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Page 1: Arylaldehydes - Sigma-Aldrich

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SIG

MA

P.O.B

OX

14508S

T.LOU

IS, M

O, U

SA

63178-9916

NewArylaldehydes

Global Bulk

Manufacturing

Combikits™

(Vials or

Titerplates)

Arylaldehyde

Resins

for SPOS

Over 80 New

Products!

Organic SynthesisBuilding Blocks for

TO ORDER

PHONE

FAX

MAIL

800-558-9160 (USA)or 414-273-3850

800-962-9591 (USA)or 414-273-4979

Aldrich Chemical CompanyP.O. Box 2060Milwaukee, WI 53201

ArgentinaSigma-Aldrich de Argentina, S.ATel: 54 11 4807 0321Fax: 54 11 4807 0346E-mail: [email protected]

AustraliaSigma-Aldrich Pty., LimitedFree Tel: 1-800-800-097Free Fax: 1-800-800-096Tel: 61-2-9841-0555Fax: 61-2-9841-0500E-mail: [email protected]

AustriaSigma-Aldrich Handels GmbHTel: 43 1 605 8110Fax: 43 1 605 8120E-mail: [email protected]

BelgiumSigma-Aldrich nv/saFree Tel: 0800-147.47Free Fax: 0800-147.45Tel: 03 899.13.01Fax: 03 899.13.11E-mail: [email protected]

BrazilSigma-Aldrich Química Brasil Ltda.Tel: 55-11-231-1866Fax: 55-11-257-9079E-mail: [email protected]

CanadaSigma-Aldrich Canada Ltd.Free Tel: 800-565-1400Free Fax: 800-265-3858Tel: 905-829-9500Fax: 905-829-9292E-mail: [email protected]

Czech RepublicSigma-Aldrich s.r.o.Tel: 00-420-2-2176 1300Fax: 00-420-2-2176 3300E-mail:[email protected]

DenmarkSigma-Aldrich Denmark A/STel: +45 43 56 59 10Fax: +45 43 56 59 05E-mail: [email protected]

EireSigma-Aldrich Ireland Ltd.Free Tel: 1 800 200 888Free Fax: 1 800 600 222Tel: 01 404 1900Fax: 01 404 1910E-mail: [email protected]

FinlandSigma-Aldrich FinlandTel: (09) 350-9250Fax: (09) 350-92555E-mail: [email protected]

FranceSigma-Aldrich Chimie S.a.r.lTel Numero Vert: 0800 21 14 08Fax Numero Vert: 0800 03 10 52E-mail: [email protected]

Germany(also SE Europe, the Baltics, Africa and theMiddle East)Sigma-Aldrich Chemie GmbHFreecall Tel: 0800-5155 000Freecall Fax: 0800-6490 000Tel: +49(0)89-6513-0Fax: +49(0)89-6513-1169E-mail: [email protected] Slovakia, Africa, Middle East and other European countries:Tel: +49(0)89-6513-1807Fax: +49(0)89-6513-1877

GreeceSigma-Aldrich (o.m) Ltd.Tel: 30-1-9948010Fax: 30-1-9943831E-mail: [email protected]

HungarySigma-Aldrich KftTel: 06-1-269-6474Fax: 06-1-235-9050E-mail: [email protected]

IndiaSigma-Aldrich CorporationBangalore location:Phone: 91 80 851 8797Fax: 91 80 851 8358

New Delhi location:Phone: (011) 689 9826Fax: (011) 689 9827E-mail: [email protected]

IsraelSigma Israel Chemicals Ltd.Toll Free Tel: 1-800-70-2222Tel: 972-8-948-4222Fax: 972-8-948-4200E-mail: [email protected]

ItalySigma-Aldrich S.r.l.Numero Verde: 800-827018Tel: 02-33417.310Fax: 02-38010.737E-mail: [email protected]

JapanSigma-Aldrich Japan K.K.Tel: 81-3-5821-3111Fax: 81-3-5821-3170

KoreaSigma-Aldrich KoreaToll Free Tel: 080-023-7111Toll Free Fax: 080-023-8111Tel: 82-2-783-5211Fax: 82-2-783-5011E-mail: [email protected]

MalaysiaSigma-Aldrich (M) Sdn BhdTel: 03-7824181, 03-7808140Fax: 03-7824067E-mail: [email protected]

MexicoSigma-Aldrich Química, S.A. de C.V.Tel Gratis: 91-800-0075300Tel: (72) 76 1600Fax: (72) 76 1601E-mail: [email protected]

NetherlandsSigma-Aldrich Chemie BVTel Gratis: 0800 022 9088Fax Gratis: 0800 022 9089Tel: 078-620 54 11Fax: 078-620 54 21E-mail: [email protected]

NorwaySigma-Aldrich Norway ASTel: 47 23 176 000Fax: 47 23 176 010E-mail: [email protected]

PolandSigma-Aldrich Sp.zo.oTel: (48-61) 823-24-81Fax: (48-61) 823-27-81E-mail: [email protected]

PortugalSigma-Aldrich Quimica S.A.Free Tel: 0800-202180Free Fax: 0800-202178E-mail, encomendas:[email protected]

RussiaSigma-Aldrich RussiaTel: 7-095-975-3321Fax: 7-095-975-4792E-mail: [email protected]

SingaporeSigma-Aldrich Pte., Ltd.Tel: (65) 271 1089Fax: (65) 271 1571E-mail: [email protected]

South AfricaSigma-Aldrich South Africa (Pty) Ltd.Tel: (011) 397 8886Fax: (011) 397 8859E-mail: [email protected]

SpainSigma-Aldrich Química S.A.Free Tel: 900-101376Free Fax: 900-102028Tel: 91-6619977Fax: 91-6619642E-mail, pedidos:[email protected]

SwedenSigma-Aldrich Sweden ABTel: 020-35 05 10Fax: 020-35 25 22Outside Sweden Tel: 46-8-742 4200Outside Sweden Fax: 46-8-742 4243E-mail: [email protected]

SwitzerlandAldrich ChemieA division of Fluka Chemie AGTel: 081-755 27 23Fax: 081-755 28 40Swiss Free Call: 0800 80 00 80E-mail: [email protected]

United KingdomSigma-Aldrich Company Ltd.Free Tel: 0800 717181Free Fax: 0800 378538Tel: 01202 733114Fax: 01202 715460E-mail: [email protected]

United StatesAldrich Chemical Company, Inc.Toll Free Tel: 1-800-558-9160Toll Free Fax: 1-800-962-9591Tel: 414-273-3850Fax: 414-273-4979E-mail: [email protected]

Sigma Chemical CompanyToll Free Tel: 1-800-521-8956Toll Free Fax: 1-800-325-5052Tel: 314-771-5765Fax: 314-771-5757E-mail: [email protected]

© 2000 Sigma-Aldrich Co. Printed in USA. Aldrich brand products are sold through Sigma-Aldrich, Inc. Sigma-Aldrich, Inc. warrants that its products conform to the information contained in thisand other Sigma-Aldrich publications. Purchaser must determine the suitability of the product(s) for their particular use. Additional terms and conditions may apply. Please see reverse side of theinvoice or packing slip. Aldrich is a registered trademark of Sigma-Aldrich. Riedel-de Haën®: trademark under license from Riedel-de Haën GmbH.

World Headquarters: 1001 W. St. Paul Ave., Milwaukee,WI 53233 USA • (001) 414-273-3850 • www.sigma-aldrich.com

Biochemicals and Reagents for Life Science Research

Specialty Chemicalsand Analytical

Reagents for Research

Laboratory Chemicalsand Reagents for

Research and Analysis

Chromatography Products for Analysis

and Purification

Organics and Inorganics for

Chemical Synthesis

The SIGMA-ALDRICHFamily

DUG

For Development/Manufacturing Quantities For Quantity Pricing/Standing OrdersContact your local Sigma-Aldrich office Contact your local Sigma-Aldrich officeand ask for Sigma-Aldrich Fine Chemicals

P.O. Box 355Milwaukee, WI 53201USA

Return Service Requested

Sigma-Aldrich Worldwide Locations

Mas

terc

ard

, Vis

a, a

nd

Am

eric

an E

xpre

ss a

ccep

ted

. N

O m

inim

um

ord

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.

ChemFiles Vol. 1, No. 2 • 2001Dess–Martin Periodinane

is widely used for the mild

oxidation of alcohols to

aldehydes and ketones.1

This reagent is especially useful

for substrates containing sensitive

functional groups and offers an

alternative to other mild

reagents (e.g. TPAP). Other

advantages such as selectivity,

rapid rates, avoiding the use of

toxic (i.e. chromium-based)

chemicals, using stoichiometric

amounts of reagent, and ease of

work up make the Dess–Martin

periodinane a reliable and easy-to-

use oxidizer in organic synthesis.

Dess–Martin PeriodinaneDess–Martin Periodinane

1. Useful in the preparation of epimerization-sensitive optically active N-protected α-amino aldehydes with high enantiomeric excess.2

2. Oximes and tosylhydrazones are converted to their corresponding carbonyl compounds under mild conditionswithout overoxidation of the final product.3

3. Oxidation of sugar hydroxyls in good yields with periodinane avoids the use of ruthenium dioxide.4

4. A highly unstable dialdehyde was prepared by oxidation with periodinane and trapped in situ with a pre-formed Wittig ylide.5

5. A convenient route to the preparation of highly reactive acyl nitroso compounds. These products can be trapped by dienes to form cycloadducts.6

6. Rapid production of complex and diverse natural product-like polycycles. A proposed mechanism starts with an ortho-oxidation followed by an intramolecular hetero Diels–Alder reaction.7

7. Neutral and mild work-up conditions avoid the formation of dehydrofluorinated by-products in the oxidation of polyfluorinated primary alcohols to aldehydes.8

27,462-3 Dess-Martin periodinane, 97% 1g; 5g[1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one]

Preparation of ArylaldehydesPreparation of ArylaldehydesVarious routes are available for the formation of arylaldehydes, including classical aromatic formylation viaVilsmeier, Gatterman, or Reimer–Tiemann reactions. Other methods include reduction of carboxylic acid derivatives,especially the reduction of esters with DIBAH9, and the oxidation of alcohols, typically with chromium reagents but accomplished under mild conditions with TPAP10 or Dess-Martin periodinane (see above).

33,074-4 Tetrapropylammonium perruthenate, 97% (TPAP) 250mg; 1g25,681-1 Diisobutylaluminum hydride (DIBAH) 100g; 1kg19,014-4 Pyridinium chlorochromate, 98% (PCC) 25g; 100g; 500g21,469-8 Pyridinium dichromate, 98% (PDC) 5g; 100g 500g

References: (1) Dess, D.B; Martin, J. C. J. Org. Chem. 1983, 48, 4155. (2) Myers, A.G. et al. Tetrahedron Lett. 2000, 41, 1359. (3) Bose, D.S.; Narsaiah, A. V. Synth. Commun.1999, 29, 937. (4) Rao, H. S. P. et al. Indian J. Chem., Sect. B. 1997, 36B, 816. (5) Barrett, A. G.M. et al. J. Org. Chem. 1997, 62, 9376. (6) Jenkins, N. E. et al. Synth. Commun.2000, 30, 947. (7) Nicolaou, K.C. et al. Angew. Chem., Int. Ed. Engl. 2000, 39, 622. (8) Lévêque, L. et al. Tetrahedron Lett. 1998. 39, 8857. (9) Winterfeldt, E. Synthesis1975, 617. (10) Ley, S.V. et al. ibid. 1994, 639.

Page 2: Arylaldehydes - Sigma-Aldrich

NO

PO

STA

GE

NE

CE

SS

AR

Y IF

MA

ILED

IN T

HE

UN

ITE

D S

TATE

S

BU

SIN

ES

S R

EP

LY M

AIL

FIR

ST

-CLA

SS

MA

IL PE

RM

IT N

O.3038 S

T.LOU

IS, M

O

PO

STA

GE

WILL B

E PA

ID B

Y A

DD

RE

SS

EE

SIG

MA

P.O.B

OX

14508S

T.LOU

IS, M

O, U

SA

63178-9916

NewArylaldehydes

Global Bulk

Manufacturing

Combikits™

(Vials or

Titerplates)

Arylaldehyde

Resins

for SPOS

Over 80 New

Products!

Organic SynthesisBuilding Blocks for

TO ORDER

PHONE

FAX

MAIL

800-558-9160 (USA)or 414-273-3850

800-962-9591 (USA)or 414-273-4979

Aldrich Chemical CompanyP.O. Box 2060Milwaukee, WI 53201

ArgentinaSigma-Aldrich de Argentina, S.ATel: 54 11 4807 0321Fax: 54 11 4807 0346E-mail: [email protected]

AustraliaSigma-Aldrich Pty., LimitedFree Tel: 1-800-800-097Free Fax: 1-800-800-096Tel: 61-2-9841-0555Fax: 61-2-9841-0500E-mail: [email protected]

AustriaSigma-Aldrich Handels GmbHTel: 43 1 605 8110Fax: 43 1 605 8120E-mail: [email protected]

BelgiumSigma-Aldrich nv/saFree Tel: 0800-147.47Free Fax: 0800-147.45Tel: 03 899.13.01Fax: 03 899.13.11E-mail: [email protected]

BrazilSigma-Aldrich Química Brasil Ltda.Tel: 55-11-231-1866Fax: 55-11-257-9079E-mail: [email protected]

CanadaSigma-Aldrich Canada Ltd.Free Tel: 800-565-1400Free Fax: 800-265-3858Tel: 905-829-9500Fax: 905-829-9292E-mail: [email protected]

Czech RepublicSigma-Aldrich s.r.o.Tel: 00-420-2-2176 1300Fax: 00-420-2-2176 3300E-mail:[email protected]

DenmarkSigma-Aldrich Denmark A/STel: +45 43 56 59 10Fax: +45 43 56 59 05E-mail: [email protected]

EireSigma-Aldrich Ireland Ltd.Free Tel: 1 800 200 888Free Fax: 1 800 600 222Tel: 01 404 1900Fax: 01 404 1910E-mail: [email protected]

FinlandSigma-Aldrich FinlandTel: (09) 350-9250Fax: (09) 350-92555E-mail: [email protected]

FranceSigma-Aldrich Chimie S.a.r.lTel Numero Vert: 0800 21 14 08Fax Numero Vert: 0800 03 10 52E-mail: [email protected]

Germany(also SE Europe, the Baltics, Africa and theMiddle East)Sigma-Aldrich Chemie GmbHFreecall Tel: 0800-5155 000Freecall Fax: 0800-6490 000Tel: +49(0)89-6513-0Fax: +49(0)89-6513-1169E-mail: [email protected] Slovakia, Africa, Middle East and other European countries:Tel: +49(0)89-6513-1807Fax: +49(0)89-6513-1877

GreeceSigma-Aldrich (o.m) Ltd.Tel: 30-1-9948010Fax: 30-1-9943831E-mail: [email protected]

HungarySigma-Aldrich KftTel: 06-1-269-6474Fax: 06-1-235-9050E-mail: [email protected]

IndiaSigma-Aldrich CorporationBangalore location:Phone: 91 80 851 8797Fax: 91 80 851 8358

New Delhi location:Phone: (011) 689 9826Fax: (011) 689 9827E-mail: [email protected]

IsraelSigma Israel Chemicals Ltd.Toll Free Tel: 1-800-70-2222Tel: 972-8-948-4222Fax: 972-8-948-4200E-mail: [email protected]

ItalySigma-Aldrich S.r.l.Numero Verde: 800-827018Tel: 02-33417.310Fax: 02-38010.737E-mail: [email protected]

JapanSigma-Aldrich Japan K.K.Tel: 81-3-5821-3111Fax: 81-3-5821-3170

KoreaSigma-Aldrich KoreaToll Free Tel: 080-023-7111Toll Free Fax: 080-023-8111Tel: 82-2-783-5211Fax: 82-2-783-5011E-mail: [email protected]

MalaysiaSigma-Aldrich (M) Sdn BhdTel: 03-7824181, 03-7808140Fax: 03-7824067E-mail: [email protected]

MexicoSigma-Aldrich Química, S.A. de C.V.Tel Gratis: 91-800-0075300Tel: (72) 76 1600Fax: (72) 76 1601E-mail: [email protected]

NetherlandsSigma-Aldrich Chemie BVTel Gratis: 0800 022 9088Fax Gratis: 0800 022 9089Tel: 078-620 54 11Fax: 078-620 54 21E-mail: [email protected]

NorwaySigma-Aldrich Norway ASTel: 47 23 176 000Fax: 47 23 176 010E-mail: [email protected]

PolandSigma-Aldrich Sp.zo.oTel: (48-61) 823-24-81Fax: (48-61) 823-27-81E-mail: [email protected]

PortugalSigma-Aldrich Quimica S.A.Free Tel: 0800-202180Free Fax: 0800-202178E-mail, encomendas:[email protected]

RussiaSigma-Aldrich RussiaTel: 7-095-975-3321Fax: 7-095-975-4792E-mail: [email protected]

SingaporeSigma-Aldrich Pte., Ltd.Tel: (65) 271 1089Fax: (65) 271 1571E-mail: [email protected]

South AfricaSigma-Aldrich South Africa (Pty) Ltd.Tel: (011) 397 8886Fax: (011) 397 8859E-mail: [email protected]

SpainSigma-Aldrich Química S.A.Free Tel: 900-101376Free Fax: 900-102028Tel: 91-6619977Fax: 91-6619642E-mail, pedidos:[email protected]

SwedenSigma-Aldrich Sweden ABTel: 020-35 05 10Fax: 020-35 25 22Outside Sweden Tel: 46-8-742 4200Outside Sweden Fax: 46-8-742 4243E-mail: [email protected]

SwitzerlandAldrich ChemieA division of Fluka Chemie AGTel: 081-755 27 23Fax: 081-755 28 40Swiss Free Call: 0800 80 00 80E-mail: [email protected]

United KingdomSigma-Aldrich Company Ltd.Free Tel: 0800 717181Free Fax: 0800 378538Tel: 01202 733114Fax: 01202 715460E-mail: [email protected]

United StatesAldrich Chemical Company, Inc.Toll Free Tel: 1-800-558-9160Toll Free Fax: 1-800-962-9591Tel: 414-273-3850Fax: 414-273-4979E-mail: [email protected]

Sigma Chemical CompanyToll Free Tel: 1-800-521-8956Toll Free Fax: 1-800-325-5052Tel: 314-771-5765Fax: 314-771-5757E-mail: [email protected]

© 2000 Sigma-Aldrich Co. Printed in USA. Aldrich brand products are sold through Sigma-Aldrich, Inc. Sigma-Aldrich, Inc. warrants that its products conform to the information contained in thisand other Sigma-Aldrich publications. Purchaser must determine the suitability of the product(s) for their particular use. Additional terms and conditions may apply. Please see reverse side of theinvoice or packing slip. Aldrich is a registered trademark of Sigma-Aldrich. Riedel-de Haën®: trademark under license from Riedel-de Haën GmbH.

World Headquarters: 1001 W. St. Paul Ave., Milwaukee,WI 53233 USA • (001) 414-273-3850 • www.sigma-aldrich.com

Biochemicals and Reagents for Life Science Research

Specialty Chemicalsand Analytical

Reagents for Research

Laboratory Chemicalsand Reagents for

Research and Analysis

Chromatography Products for Analysis

and Purification

Organics and Inorganics for

Chemical Synthesis

The SIGMA-ALDRICHFamily

DUG

For Development/Manufacturing Quantities For Quantity Pricing/Standing OrdersContact your local Sigma-Aldrich office Contact your local Sigma-Aldrich officeand ask for Sigma-Aldrich Fine Chemicals

P.O. Box 355Milwaukee, WI 53201USA

Return Service Requested

Sigma-Aldrich Worldwide Locations

Mas

terc

ard

, Vis

a, a

nd

Am

eric

an E

xpre

ss a

ccep

ted

. N

O m

inim

um

ord

er O

R c

on

firm

ing

pu

rch

ase

ord

er r

equ

ired

.

ChemFiles Vol. 1, No. 2 • 2001Dess–Martin Periodinane

is widely used for the mild

oxidation of alcohols to

aldehydes and ketones.1

This reagent is especially useful

for substrates containing sensitive

functional groups and offers an

alternative to other mild

reagents (e.g. TPAP). Other

advantages such as selectivity,

rapid rates, avoiding the use of

toxic (i.e. chromium-based)

chemicals, using stoichiometric

amounts of reagent, and ease of

work up make the Dess–Martin

periodinane a reliable and easy-to-

use oxidizer in organic synthesis.

Dess–Martin PeriodinaneDess–Martin Periodinane

1. Useful in the preparation of epimerization-sensitive optically active N-protected α-amino aldehydes with high enantiomeric excess.2

2. Oximes and tosylhydrazones are converted to their corresponding carbonyl compounds under mild conditionswithout overoxidation of the final product.3

3. Oxidation of sugar hydroxyls in good yields with periodinane avoids the use of ruthenium dioxide.4

4. A highly unstable dialdehyde was prepared by oxidation with periodinane and trapped in situ with a pre-formed Wittig ylide.5

5. A convenient route to the preparation of highly reactive acyl nitroso compounds. These products can be trapped by dienes to form cycloadducts.6

6. Rapid production of complex and diverse natural product-like polycycles. A proposed mechanism starts with an ortho-oxidation followed by an intramolecular hetero Diels–Alder reaction.7

7. Neutral and mild work-up conditions avoid the formation of dehydrofluorinated by-products in the oxidation of polyfluorinated primary alcohols to aldehydes.8

27,462-3 Dess-Martin periodinane, 97% 1g; 5g[1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one]

Preparation of ArylaldehydesPreparation of ArylaldehydesVarious routes are available for the formation of arylaldehydes, including classical aromatic formylation viaVilsmeier, Gatterman, or Reimer–Tiemann reactions. Other methods include reduction of carboxylic acid derivatives,especially the reduction of esters with DIBAH9, and the oxidation of alcohols, typically with chromium reagents but accomplished under mild conditions with TPAP10 or Dess-Martin periodinane (see above).

33,074-4 Tetrapropylammonium perruthenate, 97% (TPAP) 250mg; 1g25,681-1 Diisobutylaluminum hydride (DIBAH) 100g; 1kg19,014-4 Pyridinium chlorochromate, 98% (PCC) 25g; 100g; 500g21,469-8 Pyridinium dichromate, 98% (PDC) 5g; 100g 500g

References: (1) Dess, D.B; Martin, J. C. J. Org. Chem. 1983, 48, 4155. (2) Myers, A.G. et al. Tetrahedron Lett. 2000, 41, 1359. (3) Bose, D.S.; Narsaiah, A. V. Synth. Commun.1999, 29, 937. (4) Rao, H. S. P. et al. Indian J. Chem., Sect. B. 1997, 36B, 816. (5) Barrett, A. G.M. et al. J. Org. Chem. 1997, 62, 9376. (6) Jenkins, N. E. et al. Synth. Commun.2000, 30, 947. (7) Nicolaou, K.C. et al. Angew. Chem., Int. Ed. Engl. 2000, 39, 622. (8) Lévêque, L. et al. Tetrahedron Lett. 1998. 39, 8857. (9) Winterfeldt, E. Synthesis1975, 617. (10) Ley, S.V. et al. ibid. 1994, 639.

Page 3: Arylaldehydes - Sigma-Aldrich

Arylaldehydes

54,264-4 Mol. Wt.C8H7FO2 154.14

1g5g

O

H

F

O

52,681-9 Mol. Wt.C8H7FO3 170.14

1g

O

HO

F

HO

51,513-2 Mol. Wt.C8H7FO 138.14

5g

O

H

F

51,832-8 Mol. Wt.C8H7NO3 165.15

1g

O

H

NO2

52,898-6 Mol. Wt.C8H7FO2 154.14

25g

O

H

O F

51,576-0 Mol. Wt.C8H7NO4 181.15

5g

O

H

O

O2N

52,662-2 Mol. Wt.C8H6ClFO 172.58

1g5g

O

H

F

Cl

53,673-3 Mol. Wt.C8H7FO2 154.14

1g5g

O

H

F

O

51,642-2 Mol. Wt.C8H7NO4 181.15

5g

O

H

O

NO2

51,383-0 Mol. Wt.C9H7NO 145.16

5g

NH

O

H

52,661-4 Mol. Wt.C8H6ClFO 172.58

1g5g

O

H

Cl

F

52,310-0 Mol. Wt.C8H7FO2 154.14

1g5g

O

H

O

F

52,311-9 Mol. Wt.C8H8OS 152.22

5g

O

H

S

52,306-2 Mol. Wt.C9H8O 132.16

5g

O

H

52,923-0 Mol. Wt.C8H6F2O2 172.12

5g

O

H

OCF2H

52,314-3 Mol. Wt.C8H7FO 138.14

5g

O

H

F

51,286-9 Mol. Wt.C8H9BO4 179.97

5g25g

O

H

B(OH)2

O

51,874-3 Mol. Wt.C9H6BrNO 224.06

5g

NH

O

HBr

34,854-6 Mol. Wt.C9H9FO3 184.16

1g

O

H

O

O

F

51,806-9 Mol. Wt.C9H10O 134.18

1g5g

O

H

51,805-0 Mol. Wt.

C9H10O 134.18

5g

O

H

52,640-1 Mol. Wt.C9H4F6O 242.12

1g5g

O

H

CF3F3C

53,307-6 Mol. Wt.C9H6ClNO 179.60

5g

NH

O

HCl

51,575-2 Mol. Wt.C9H9BrO2 229.08

5g

O

H

O

Br

TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com

51,515-9 Mol. Wt.C9H10O 134.18

5g

O

H

51,535-3 Mol. Wt.C9H10O 134.18

1g5g

O

H

49,385-6 Mol. Wt.C9H10O 134.18

1g5g

O

H

54,382-9 Mol. Wt.C10H4FNO5 237.14

1g

O

O

H

O

F

NO2

51,631-7 Mol. Wt.C9H10O2 150.18

1g5g

O

H

O

54,372-1 Mol. Wt.C10H6ClFO2 212.60

1g

O

O

H

Cl

F

54,362-4 Mol. Wt.C10H5FO3 192.15

1g

O

O

H

O

F

51,632-5 Mol. Wt.C9H10O2 150.18

5g

Arylaldehyde chemistry has led to a wealth of diverse products, so naturally Aldrich is determined to offer thewidest possible breadth of substitution patterns. Target molecules prepared from groups of arylaldehydes haveincluded aminoindenes,1 quinolines,2 arylglycines,3 and homoallylic alcohols.4 With over 400 arylaldehydes amongthe more than 80,000 products in stock at Sigma-Aldrich, chances are you’ll find what you’re looking for!

(1) Katritzky, A. R. et al. J. Org. Chem. 2000, 65, 8066. (2) Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1996, 118, 8977. (3) Beller, M. et al. J. Org. Chem. 1998, 63,5658. (4) Curran, D.P.; Zhiyong, L. Med. Chem. Res. 1998, 8, 261. 1. What type of chemistry do you routinely perform?

❍ General Organic Chemistry [ORGS] ❍ Organometallics [ORGM]❍ Organic Combinatorial [COCH] ❍ Polymer Chemistry [POLY]❍ Chiral Chemistry [CHIR] ❍ Drug Discovery [DRUG]

2. Please check any of the following FREE catalog and literature piecesthat you would like to receive.❍ Aldrich Handbook [002]❍ Sigma General Catalog [001]❍ Fluka/Riedel-de-Haën® Catalog [003]❍ Aldrichimica Acta [032]❍ Resins for Combichem [DLW]❍ Combikits™/Small Sample Service [CBJ]❍ Polymer Products CD [DGQ]❍ New Fluorinated Products [DEO]❍ Products for Suzuki Coupling [DTK]

3. What other specialized grouping would be of interest to you?❍ Oxidizing agents [3AA] ❍ Terminal alkenes [3AE]❍ Reducing agents [3AB] ❍ Sulfonyl chlorides [3AF]❍ Oximes [3AC] ❍ Nitriles [3AG]❍ Terminal alkynes [3AD] ❍ Other _____________________

4. ❍ I would like to receive a FREE CD-ROM with product listingsfrom the Sigma-Aldrich Library of Rare Chemicals. [DDH]

Fluka/Riedel-de-Haën and Combikits are a registered trademark and trademark, respectively, of Sigma-Aldrich Co.

Purpald®, an aminotriazole, continues to be useful as a complexation reagent for the spectrophotomeric determination of aldehydes, e.g., in drug concentrationanalyses and in determining airborne formaldehyde.Ketones, esters, formic acid, amides, hydroxylamines,quinones, uric acid, hydrazines and aminophenols do not react with Purpald® to yield purple products.1-2

For properties, procedure for detecting aldehydes, applications, and references of Purpald®, please contact our Technical Services department at 800-231-8327(USA)or your local office and request Aldrich Technical Bulletin#AL-145; or visit our Web site, www.sigma-aldrich.com/aldrichand click on Technical Bulletins.

16,289-2 Purpald®, 99+%(4-amino-3-hydrazino-5-mercapto-1,2,4-triazole)

5g; 25g; 100g

53,145-6 Mol. Wt.C5H3ClO2 130.53

1g

OCl

O

H

49,990-0 Mol. Wt.C5H5BO3S 155.97

1g5g

S

O

H

B(OH)2

51,405-5 Mol. Wt.C5H5BO3S 155.97

1g5g

S(HO)2B

H

O

49,991-9 Mol. Wt.C5H5BO3S 155.97

1g5g

S

O

H

B(OH)2

52,642-8 Mol. Wt.C7H3ClF2O 176.55

1g5g

O

H

F

Cl

F

52,391-7 Mol. Wt.C7H4Cl2O 175.01

5g

O

H

Cl

Cl

52,919-2 Mol. Wt.C7H3F3O 160.10

1mL5mL

O

H

F

F

F

54,331-4 Mol. Wt.C7H4FIO 250.01

1g

O

H

F

I

52,917-6 Mol. Wt.C7H3F3O 160.10

5mL

O

H

F

F

F

53,724-1 Mol. Wt.C7H4ClFO 158.56

1g5g

O

H

Cl

F

52,742-4 Mol. Wt.C7H5NO4 167.12

1g5g

O

H

OH

NO2

49,386-4 Mol. Wt.C7H6O4 154.12

1g

O

H

OHHO

HO

53,306-8 Mol. Wt.C7H7NO2 137.14

5g

N

O

H

O

52,918-4 Mol. Wt.C7H3F3O 160.10

1g5g

O

HF

F F

52,660-6 Mol. Wt.C7H4ClFO 158.56

1g5g

O

H

Cl

F

52,627-4 Mol. Wt.C7H5FO2 140.11

1g

O

H

OH

F

TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com

52,569-3 Mol. Wt.C6H4BrNO 186.01

1g10g

NBr

O

H

52,659-2 Mol. Wt.C7H3ClF2O 176.55

1g5g

O

H

Cl

F

F

51,830-1 Mol. Wt.C7H4FNO3 169.11

1g

O

H

NO2

F

51,677-5 Mol. Wt.C7H5BrO2 201.02

5g

O

H

Br

HO

52,887-0 Mol. Wt.C7H4BrFO 203.01

25g

O

HBr

F

52,663-0 Mol. Wt.C8H3ClF4O 226.56

1g5g

O

H

Cl

F

F3C

52,664-9 Mol. Wt.C8H3ClF4O 226.56

1g5g

O

H

Cl

F

CF3

52,897-8 Mol. Wt.C7H4BrFO 203.01

1g5g

O

HF

Br

52,921-4 Mol. Wt.C8H4F4O 192.10

1g5g

O

H

FF3C

52,914-1 Mol. Wt.C8H5F3OS 206.17

5g

O

H

SF3C

52,920-6 Mol. Wt.C8H4F4O 192.10

1g5g

O

HF3C

F

51,574-4 Mol. Wt.C8H6Br2O2 293.95

5g

O

H

O

Br

Br

52,916-8 Mol. Wt.C8H5F3O2 190.11

1g5g

O

H

O

CF3

52,922-2 Mol. Wt.C8H4F4O 192.10

1mL10mL

52,667-3 Mol. Wt.C11H8O2 172.18

1g5g

O

O

H

52,386-0 Mol. Wt.C11H12N2O 188.23

25g

O

H

N

CN

E540-9 Mol. Wt.C10H12O3 180.20

5g

O

H

O

O

51,804-2 Mol. Wt.C11H14O 162.23

5g

O

H

53,565-6 Mol. Wt.C11H8ClNO 205.64

1g

N

O

H

Cl

51,678-3 Mol. Wt.C11H14O3 194.23

5g

O

H

O

O

13,413-9 Mol. Wt.C10H9NO 159.19

1g5g

NH

O

H

53,564-8 Mol. Wt.C11H8ClNO 205.64

5g

N

O

H

Cl

51,630-9 Mol. Wt.C11H14O3 194.23

5g

O

H

OO

54,332-2 Mol. Wt.C15H11NO 221.26

1g5g

NH

O

H

51,112-9 Mol. Wt.C10H9NO 159.19

5g

N

O

H

49,399-6 Mol. Wt.C11H8ClNO2 221.65

5g

N

O

H

Cl

O

52,648-7 Mol. Wt.C12H10O 170.21

1g10g

OH

40,587-6 Mol. Wt.C15H12N2O2 252.27

1g5g

NNH

O

HO

52,645-2 Mol. Wt.C10H12O2 148.21

1g10g

O

H

51,640-6 Mol. Wt.C10H12O3 180.21

5g

53,308-4 Mol. Wt.C12H10O2 186.21

5g

O

H

O

49,974-9 Mol. Wt.C14H12O2 212.25

10mL50mL

O

H

O

52,338-0 Mol. Wt.C12H14OSi 202.33

5g

O

H

TMSi

54,981-9 Mol. Wt.C15H10FNO 239.24

1g5g

NH

O

H

F

TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com

49,387-2 Mol. Wt.C16H16O2 240.30

1g

O

H

O

51,577-9 Mol. Wt.C16H24O2 248.37

5g

O

H

O

52,665-7 Mol. Wt.C13H10O 182.22

5g

OH

54,333-0 Mol. Wt.C14H11BrO2 291.14

1g10g

O

H

O

Br

ArylaldehydesArylaldehydes

TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com

TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com

TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com

Arylaldehyde Resins for SPOS

Scavenger Resins5

for Aldehydes

References: (1) Wilson, T.W. et al. Tetrahedron Lett. 1997,38, 7151. (2) Sarantakis, D. et al. Tetrahedron Lett. 1997,38, 7325. (3) Bilodeau, M.T. et al. J. Org. Chem. 1998, 63,2800. (4) Estep, K.G. et al. J. Org. Chem. 1998, 63, 5300. (5) Kaldor, S.W. et al. Tetrahedron Lett. 1996, 40, 7193.

The following resins are useful for thesolid phase preparation of secondarysulfonamides, amides, ureas, and carbamates, and feature dilute-acid-labile linkers.1-4

Base resin

51,644-9AMEBA resin, 100-200 mesh, 1% cross-linked, 1.0-1.5 mmol/g

1g; 5g53,821-34-Benzyloxy-2,6-dimethoxybenz-aldehyde, polymer-bound, 100-200 mesh, 1% cross-linked

1g; 5g; 25g

51,627-93-Formyl-1-indoleacetic acid, polymer-bound

1g; 5g; 25g

53,240-1Formylpolystyrene, 100-200 mesh, 1% cross-linked, 0.7-1.5 mmol/g

1g; 5g; 25g

47,978-0Diethylenetriamine, polymer-bound, 2.5-3.0 mmol N/g

5g; 25g47,209-3Ethylenediamine, polymer-bound,1% cross-linked, 2.5-3.0 mmol N/g

5g; 25g

53,233-9p-Toluenesulfonyl hydrazide, polymer-bound, 1% cross-linked, 100-200 mesh, ~1.5 mmol N/g

1g; 5g; 25g

Please call us at 800-336-9719 (USA) or 314-534-4900, contact your localSigma-Aldrich office, or visit us at

www.sigma-aldrich.com/safc.

Sigma-Aldrich Fine Chemicals is readyto provide a competitive bulk quote

on any of our products includingthose listed in this publication.

✔ Prompt delivery of the broadestrange of chemicals from stock.

✔ Extensive custom processdevelopment and scaleup.

✔ New large scale & cGMP manufacturing facilities worldwide.

✔ Custom packaging.

✔ Analytical services & regulatory support.

We offer:

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A reagent thatturns aldehydespurple!

Purpald®

References: (1) Hopps, H.B. Aldrichimica Acta 2000, 33, 28. (2) Dickinson, R.G.; Jacobsen, N.W. Chem Commun. 1970, 1719.Purpald is a registered trademark of Sigma-Aldrich Co.

O

H

F

F3C

O

H

O

O

H

O

O

The emerging importance of combinatorial and high-throughput methods in chemistryhas resulted in a need for specialized kits of chemicals. We are able to provide a variety of these kits by combining Aldrich’s vast chemical inventory and our customizedweighing process. Some of our more popular kits have included carboxylic acids, arylboronic acids, amines, and alcohols, and we are now pleased to add isocyanates tothis list. Please contact us. We can create a kit tailored to your specific requirements.

Key Features Include:Flexibility

❖ Ideal for high-throughput or combinatorial chemistry; available in vials or titerplates

No Minimum Order❖ Service as diverse as your needs

Reduces Waste❖ Little or no unused product to store or dispose

Saves Time❖ Less time weighing reagents, more time doing research

For more information on this unique service, please call us at800-333-7306 (USA) or e-mail us at [email protected].

In Europe, e-mail us at [email protected].

Aldrich Offers CombiKits™

CombiKits™ is a trademark of Sigma-Aldrich Co.

CGM

For a complete listing of all of our arylaldehydes, please visit our Web site at www.sigma-aldrich.com/aldrich, go to the Organics area, and click on Specialty Areas; or contact our Technical Services department by phone, 800-231-8327 (USA),

fax, 414-287-4079, or e-mail, [email protected]. As always, new product suggestions are welcome and appreciated.

Essential Tools for Today’s Synthetic Chemist

Page 4: Arylaldehydes - Sigma-Aldrich

Arylaldehydes

54,264-4 Mol. Wt.C8H7FO2 154.14

1g5g

O

H

F

O

52,681-9 Mol. Wt.C8H7FO3 170.14

1g

O

HO

F

HO

51,513-2 Mol. Wt.C8H7FO 138.14

5g

O

H

F

51,832-8 Mol. Wt.C8H7NO3 165.15

1g

O

H

NO2

52,898-6 Mol. Wt.C8H7FO2 154.14

25g

O

H

O F

51,576-0 Mol. Wt.C8H7NO4 181.15

5g

O

H

O

O2N

52,662-2 Mol. Wt.C8H6ClFO 172.58

1g5g

O

H

F

Cl

53,673-3 Mol. Wt.C8H7FO2 154.14

1g5g

O

H

F

O

51,642-2 Mol. Wt.C8H7NO4 181.15

5g

O

H

O

NO2

51,383-0 Mol. Wt.C9H7NO 145.16

5g

NH

O

H

52,661-4 Mol. Wt.C8H6ClFO 172.58

1g5g

O

H

Cl

F

52,310-0 Mol. Wt.C8H7FO2 154.14

1g5g

O

H

O

F

52,311-9 Mol. Wt.C8H8OS 152.22

5g

O

H

S

52,306-2 Mol. Wt.C9H8O 132.16

5g

O

H

52,923-0 Mol. Wt.C8H6F2O2 172.12

5g

O

H

OCF2H

52,314-3 Mol. Wt.C8H7FO 138.14

5g

O

H

F

51,286-9 Mol. Wt.C8H9BO4 179.97

5g25g

O

H

B(OH)2

O

51,874-3 Mol. Wt.C9H6BrNO 224.06

5g

NH

O

HBr

34,854-6 Mol. Wt.C9H9FO3 184.16

1g

O

H

O

O

F

51,806-9 Mol. Wt.C9H10O 134.18

1g5g

O

H

51,805-0 Mol. Wt.

C9H10O 134.18

5g

O

H

52,640-1 Mol. Wt.C9H4F6O 242.12

1g5g

O

H

CF3F3C

53,307-6 Mol. Wt.C9H6ClNO 179.60

5g

NH

O

HCl

51,575-2 Mol. Wt.C9H9BrO2 229.08

5g

O

H

O

Br

TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com

51,515-9 Mol. Wt.C9H10O 134.18

5g

O

H

51,535-3 Mol. Wt.C9H10O 134.18

1g5g

O

H

49,385-6 Mol. Wt.C9H10O 134.18

1g5g

O

H

54,382-9 Mol. Wt.C10H4FNO5 237.14

1g

O

O

H

O

F

NO2

51,631-7 Mol. Wt.C9H10O2 150.18

1g5g

O

H

O

54,372-1 Mol. Wt.C10H6ClFO2 212.60

1g

O

O

H

Cl

F

54,362-4 Mol. Wt.C10H5FO3 192.15

1g

O

O

H

O

F

51,632-5 Mol. Wt.C9H10O2 150.18

5g

Arylaldehyde chemistry has led to a wealth of diverse products, so naturally Aldrich is determined to offer thewidest possible breadth of substitution patterns. Target molecules prepared from groups of arylaldehydes haveincluded aminoindenes,1 quinolines,2 arylglycines,3 and homoallylic alcohols.4 With over 400 arylaldehydes amongthe more than 80,000 products in stock at Sigma-Aldrich, chances are you’ll find what you’re looking for!

(1) Katritzky, A. R. et al. J. Org. Chem. 2000, 65, 8066. (2) Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1996, 118, 8977. (3) Beller, M. et al. J. Org. Chem. 1998, 63,5658. (4) Curran, D.P.; Zhiyong, L. Med. Chem. Res. 1998, 8, 261. 1. What type of chemistry do you routinely perform?

❍ General Organic Chemistry [ORGS] ❍ Organometallics [ORGM]❍ Organic Combinatorial [COCH] ❍ Polymer Chemistry [POLY]❍ Chiral Chemistry [CHIR] ❍ Drug Discovery [DRUG]

2. Please check any of the following FREE catalog and literature piecesthat you would like to receive.❍ Aldrich Handbook [002]❍ Sigma General Catalog [001]❍ Fluka/Riedel-de-Haën® Catalog [003]❍ Aldrichimica Acta [032]❍ Resins for Combichem [DLW]❍ Combikits™/Small Sample Service [CBJ]❍ Polymer Products CD [DGQ]❍ New Fluorinated Products [DEO]❍ Products for Suzuki Coupling [DTK]

3. What other specialized grouping would be of interest to you?❍ Oxidizing agents [3AA] ❍ Terminal alkenes [3AE]❍ Reducing agents [3AB] ❍ Sulfonyl chlorides [3AF]❍ Oximes [3AC] ❍ Nitriles [3AG]❍ Terminal alkynes [3AD] ❍ Other _____________________

4. ❍ I would like to receive a FREE CD-ROM with product listingsfrom the Sigma-Aldrich Library of Rare Chemicals. [DDH]

Fluka/Riedel-de-Haën and Combikits are a registered trademark and trademark, respectively, of Sigma-Aldrich Co.

Purpald®, an aminotriazole, continues to be useful as a complexation reagent for the spectrophotomeric determination of aldehydes, e.g., in drug concentrationanalyses and in determining airborne formaldehyde.Ketones, esters, formic acid, amides, hydroxylamines,quinones, uric acid, hydrazines and aminophenols do not react with Purpald® to yield purple products.1-2

For properties, procedure for detecting aldehydes, applications, and references of Purpald®, please contact our Technical Services department at 800-231-8327(USA)or your local office and request Aldrich Technical Bulletin#AL-145; or visit our Web site, www.sigma-aldrich.com/aldrichand click on Technical Bulletins.

16,289-2 Purpald®, 99+%(4-amino-3-hydrazino-5-mercapto-1,2,4-triazole)

5g; 25g; 100g

53,145-6 Mol. Wt.C5H3ClO2 130.53

1g

OCl

O

H

49,990-0 Mol. Wt.C5H5BO3S 155.97

1g5g

S

O

H

B(OH)2

51,405-5 Mol. Wt.C5H5BO3S 155.97

1g5g

S(HO)2B

H

O

49,991-9 Mol. Wt.C5H5BO3S 155.97

1g5g

S

O

H

B(OH)2

52,642-8 Mol. Wt.C7H3ClF2O 176.55

1g5g

O

H

F

Cl

F

52,391-7 Mol. Wt.C7H4Cl2O 175.01

5g

O

H

Cl

Cl

52,919-2 Mol. Wt.C7H3F3O 160.10

1mL5mL

O

H

F

F

F

54,331-4 Mol. Wt.C7H4FIO 250.01

1g

O

H

F

I

52,917-6 Mol. Wt.C7H3F3O 160.10

5mL

O

H

F

F

F

53,724-1 Mol. Wt.C7H4ClFO 158.56

1g5g

O

H

Cl

F

52,742-4 Mol. Wt.C7H5NO4 167.12

1g5g

O

H

OH

NO2

49,386-4 Mol. Wt.C7H6O4 154.12

1g

O

H

OHHO

HO

53,306-8 Mol. Wt.C7H7NO2 137.14

5g

N

O

H

O

52,918-4 Mol. Wt.C7H3F3O 160.10

1g5g

O

HF

F F

52,660-6 Mol. Wt.C7H4ClFO 158.56

1g5g

O

H

Cl

F

52,627-4 Mol. Wt.C7H5FO2 140.11

1g

O

H

OH

F

TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com

52,569-3 Mol. Wt.C6H4BrNO 186.01

1g10g

NBr

O

H

52,659-2 Mol. Wt.C7H3ClF2O 176.55

1g5g

O

H

Cl

F

F

51,830-1 Mol. Wt.C7H4FNO3 169.11

1g

O

H

NO2

F

51,677-5 Mol. Wt.C7H5BrO2 201.02

5g

O

H

Br

HO

52,887-0 Mol. Wt.C7H4BrFO 203.01

25g

O

HBr

F

52,663-0 Mol. Wt.C8H3ClF4O 226.56

1g5g

O

H

Cl

F

F3C

52,664-9 Mol. Wt.C8H3ClF4O 226.56

1g5g

O

H

Cl

F

CF3

52,897-8 Mol. Wt.C7H4BrFO 203.01

1g5g

O

HF

Br

52,921-4 Mol. Wt.C8H4F4O 192.10

1g5g

O

H

FF3C

52,914-1 Mol. Wt.C8H5F3OS 206.17

5g

O

H

SF3C

52,920-6 Mol. Wt.C8H4F4O 192.10

1g5g

O

HF3C

F

51,574-4 Mol. Wt.C8H6Br2O2 293.95

5g

O

H

O

Br

Br

52,916-8 Mol. Wt.C8H5F3O2 190.11

1g5g

O

H

O

CF3

52,922-2 Mol. Wt.C8H4F4O 192.10

1mL10mL

52,667-3 Mol. Wt.C11H8O2 172.18

1g5g

O

O

H

52,386-0 Mol. Wt.C11H12N2O 188.23

25g

O

H

N

CN

E540-9 Mol. Wt.C10H12O3 180.20

5g

O

H

O

O

51,804-2 Mol. Wt.C11H14O 162.23

5g

O

H

53,565-6 Mol. Wt.C11H8ClNO 205.64

1g

N

O

H

Cl

51,678-3 Mol. Wt.C11H14O3 194.23

5g

O

H

O

O

13,413-9 Mol. Wt.C10H9NO 159.19

1g5g

NH

O

H

53,564-8 Mol. Wt.C11H8ClNO 205.64

5g

N

O

H

Cl

51,630-9 Mol. Wt.C11H14O3 194.23

5g

O

H

OO

54,332-2 Mol. Wt.C15H11NO 221.26

1g5g

NH

O

H

51,112-9 Mol. Wt.C10H9NO 159.19

5g

N

O

H

49,399-6 Mol. Wt.C11H8ClNO2 221.65

5g

N

O

H

Cl

O

52,648-7 Mol. Wt.C12H10O 170.21

1g10g

OH

40,587-6 Mol. Wt.C15H12N2O2 252.27

1g5g

NNH

O

HO

52,645-2 Mol. Wt.C10H12O2 148.21

1g10g

O

H

51,640-6 Mol. Wt.C10H12O3 180.21

5g

53,308-4 Mol. Wt.C12H10O2 186.21

5g

O

H

O

49,974-9 Mol. Wt.C14H12O2 212.25

10mL50mL

O

H

O

52,338-0 Mol. Wt.C12H14OSi 202.33

5g

O

H

TMSi

54,981-9 Mol. Wt.C15H10FNO 239.24

1g5g

NH

O

H

F

TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com

49,387-2 Mol. Wt.C16H16O2 240.30

1g

O

H

O

51,577-9 Mol. Wt.C16H24O2 248.37

5g

O

H

O

52,665-7 Mol. Wt.C13H10O 182.22

5g

OH

54,333-0 Mol. Wt.C14H11BrO2 291.14

1g10g

O

H

O

Br

ArylaldehydesArylaldehydes

TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com

TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com

TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com

Arylaldehyde Resins for SPOS

Scavenger Resins5

for Aldehydes

References: (1) Wilson, T.W. et al. Tetrahedron Lett. 1997,38, 7151. (2) Sarantakis, D. et al. Tetrahedron Lett. 1997,38, 7325. (3) Bilodeau, M.T. et al. J. Org. Chem. 1998, 63,2800. (4) Estep, K.G. et al. J. Org. Chem. 1998, 63, 5300. (5) Kaldor, S.W. et al. Tetrahedron Lett. 1996, 40, 7193.

The following resins are useful for thesolid phase preparation of secondarysulfonamides, amides, ureas, and carbamates, and feature dilute-acid-labile linkers.1-4

Base resin

51,644-9AMEBA resin, 100-200 mesh, 1% cross-linked, 1.0-1.5 mmol/g

1g; 5g53,821-34-Benzyloxy-2,6-dimethoxybenz-aldehyde, polymer-bound, 100-200 mesh, 1% cross-linked

1g; 5g; 25g

51,627-93-Formyl-1-indoleacetic acid, polymer-bound

1g; 5g; 25g

53,240-1Formylpolystyrene, 100-200 mesh, 1% cross-linked, 0.7-1.5 mmol/g

1g; 5g; 25g

47,978-0Diethylenetriamine, polymer-bound, 2.5-3.0 mmol N/g

5g; 25g47,209-3Ethylenediamine, polymer-bound,1% cross-linked, 2.5-3.0 mmol N/g

5g; 25g

53,233-9p-Toluenesulfonyl hydrazide, polymer-bound, 1% cross-linked, 100-200 mesh, ~1.5 mmol N/g

1g; 5g; 25g

Please call us at 800-336-9719 (USA) or 314-534-4900, contact your localSigma-Aldrich office, or visit us at

www.sigma-aldrich.com/safc.

Sigma-Aldrich Fine Chemicals is readyto provide a competitive bulk quote

on any of our products includingthose listed in this publication.

✔ Prompt delivery of the broadestrange of chemicals from stock.

✔ Extensive custom processdevelopment and scaleup.

✔ New large scale & cGMP manufacturing facilities worldwide.

✔ Custom packaging.

✔ Analytical services & regulatory support.

We offer:

Name _____________________________________________________________

Company __________________________________________________________

Department____________________________ Mail Stop__________________

Address _______________________________________ Bldg/Rm # _________

City_______________ State____ Country___________ Postal Code________

Phone________________ Fax _________________ E-mail_________________

Tell Us About YourselfTell Us About Yourself

A reagent thatturns aldehydespurple!

Purpald®

References: (1) Hopps, H.B. Aldrichimica Acta 2000, 33, 28. (2) Dickinson, R.G.; Jacobsen, N.W. Chem Commun. 1970, 1719.Purpald is a registered trademark of Sigma-Aldrich Co.

O

H

F

F3C

O

H

O

O

H

O

O

The emerging importance of combinatorial and high-throughput methods in chemistryhas resulted in a need for specialized kits of chemicals. We are able to provide a variety of these kits by combining Aldrich’s vast chemical inventory and our customizedweighing process. Some of our more popular kits have included carboxylic acids, arylboronic acids, amines, and alcohols, and we are now pleased to add isocyanates tothis list. Please contact us. We can create a kit tailored to your specific requirements.

Key Features Include:Flexibility

❖ Ideal for high-throughput or combinatorial chemistry; available in vials or titerplates

No Minimum Order❖ Service as diverse as your needs

Reduces Waste❖ Little or no unused product to store or dispose

Saves Time❖ Less time weighing reagents, more time doing research

For more information on this unique service, please call us at800-333-7306 (USA) or e-mail us at [email protected].

In Europe, e-mail us at [email protected].

Aldrich Offers CombiKits™

CombiKits™ is a trademark of Sigma-Aldrich Co.

CGM

For a complete listing of all of our arylaldehydes, please visit our Web site at www.sigma-aldrich.com/aldrich, go to the Organics area, and click on Specialty Areas; or contact our Technical Services department by phone, 800-231-8327 (USA),

fax, 414-287-4079, or e-mail, [email protected]. As always, new product suggestions are welcome and appreciated.

Essential Tools for Today’s Synthetic Chemist

Page 5: Arylaldehydes - Sigma-Aldrich

Arylaldehydes

54,264-4 Mol. Wt.C8H7FO2 154.14

1g5g

O

H

F

O

52,681-9 Mol. Wt.C8H7FO3 170.14

1g

O

HO

F

HO

51,513-2 Mol. Wt.C8H7FO 138.14

5g

O

H

F

51,832-8 Mol. Wt.C8H7NO3 165.15

1g

O

H

NO2

52,898-6 Mol. Wt.C8H7FO2 154.14

25g

O

H

O F

51,576-0 Mol. Wt.C8H7NO4 181.15

5g

O

H

O

O2N

52,662-2 Mol. Wt.C8H6ClFO 172.58

1g5g

O

H

F

Cl

53,673-3 Mol. Wt.C8H7FO2 154.14

1g5g

O

H

F

O

51,642-2 Mol. Wt.C8H7NO4 181.15

5g

O

H

O

NO2

51,383-0 Mol. Wt.C9H7NO 145.16

5g

NH

O

H

52,661-4 Mol. Wt.C8H6ClFO 172.58

1g5g

O

H

Cl

F

52,310-0 Mol. Wt.C8H7FO2 154.14

1g5g

O

H

O

F

52,311-9 Mol. Wt.C8H8OS 152.22

5g

O

H

S

52,306-2 Mol. Wt.C9H8O 132.16

5g

O

H

52,923-0 Mol. Wt.C8H6F2O2 172.12

5g

O

H

OCF2H

52,314-3 Mol. Wt.C8H7FO 138.14

5g

O

H

F

51,286-9 Mol. Wt.C8H9BO4 179.97

5g25g

O

H

B(OH)2

O

51,874-3 Mol. Wt.C9H6BrNO 224.06

5g

NH

O

HBr

34,854-6 Mol. Wt.C9H9FO3 184.16

1g

O

H

O

O

F

51,806-9 Mol. Wt.C9H10O 134.18

1g5g

O

H

51,805-0 Mol. Wt.

C9H10O 134.18

5g

O

H

52,640-1 Mol. Wt.C9H4F6O 242.12

1g5g

O

H

CF3F3C

53,307-6 Mol. Wt.C9H6ClNO 179.60

5g

NH

O

HCl

51,575-2 Mol. Wt.C9H9BrO2 229.08

5g

O

H

O

Br

TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com

51,515-9 Mol. Wt.C9H10O 134.18

5g

O

H

51,535-3 Mol. Wt.C9H10O 134.18

1g5g

O

H

49,385-6 Mol. Wt.C9H10O 134.18

1g5g

O

H

54,382-9 Mol. Wt.C10H4FNO5 237.14

1g

O

O

H

O

F

NO2

51,631-7 Mol. Wt.C9H10O2 150.18

1g5g

O

H

O

54,372-1 Mol. Wt.C10H6ClFO2 212.60

1g

O

O

H

Cl

F

54,362-4 Mol. Wt.C10H5FO3 192.15

1g

O

O

H

O

F

51,632-5 Mol. Wt.C9H10O2 150.18

5g

Arylaldehyde chemistry has led to a wealth of diverse products, so naturally Aldrich is determined to offer thewidest possible breadth of substitution patterns. Target molecules prepared from groups of arylaldehydes haveincluded aminoindenes,1 quinolines,2 arylglycines,3 and homoallylic alcohols.4 With over 400 arylaldehydes amongthe more than 80,000 products in stock at Sigma-Aldrich, chances are you’ll find what you’re looking for!

(1) Katritzky, A. R. et al. J. Org. Chem. 2000, 65, 8066. (2) Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1996, 118, 8977. (3) Beller, M. et al. J. Org. Chem. 1998, 63,5658. (4) Curran, D.P.; Zhiyong, L. Med. Chem. Res. 1998, 8, 261. 1. What type of chemistry do you routinely perform?

❍ General Organic Chemistry [ORGS] ❍ Organometallics [ORGM]❍ Organic Combinatorial [COCH] ❍ Polymer Chemistry [POLY]❍ Chiral Chemistry [CHIR] ❍ Drug Discovery [DRUG]

2. Please check any of the following FREE catalog and literature piecesthat you would like to receive.❍ Aldrich Handbook [002]❍ Sigma General Catalog [001]❍ Fluka/Riedel-de-Haën® Catalog [003]❍ Aldrichimica Acta [032]❍ Resins for Combichem [DLW]❍ Combikits™/Small Sample Service [CBJ]❍ Polymer Products CD [DGQ]❍ New Fluorinated Products [DEO]❍ Products for Suzuki Coupling [DTK]

3. What other specialized grouping would be of interest to you?❍ Oxidizing agents [3AA] ❍ Terminal alkenes [3AE]❍ Reducing agents [3AB] ❍ Sulfonyl chlorides [3AF]❍ Oximes [3AC] ❍ Nitriles [3AG]❍ Terminal alkynes [3AD] ❍ Other _____________________

4. ❍ I would like to receive a FREE CD-ROM with product listingsfrom the Sigma-Aldrich Library of Rare Chemicals. [DDH]

Fluka/Riedel-de-Haën and Combikits are a registered trademark and trademark, respectively, of Sigma-Aldrich Co.

Purpald®, an aminotriazole, continues to be useful as a complexation reagent for the spectrophotomeric determination of aldehydes, e.g., in drug concentrationanalyses and in determining airborne formaldehyde.Ketones, esters, formic acid, amides, hydroxylamines,quinones, uric acid, hydrazines and aminophenols do not react with Purpald® to yield purple products.1-2

For properties, procedure for detecting aldehydes, applications, and references of Purpald®, please contact our Technical Services department at 800-231-8327(USA)or your local office and request Aldrich Technical Bulletin#AL-145; or visit our Web site, www.sigma-aldrich.com/aldrichand click on Technical Bulletins.

16,289-2 Purpald®, 99+%(4-amino-3-hydrazino-5-mercapto-1,2,4-triazole)

5g; 25g; 100g

53,145-6 Mol. Wt.C5H3ClO2 130.53

1g

OCl

O

H

49,990-0 Mol. Wt.C5H5BO3S 155.97

1g5g

S

O

H

B(OH)2

51,405-5 Mol. Wt.C5H5BO3S 155.97

1g5g

S(HO)2B

H

O

49,991-9 Mol. Wt.C5H5BO3S 155.97

1g5g

S

O

H

B(OH)2

52,642-8 Mol. Wt.C7H3ClF2O 176.55

1g5g

O

H

F

Cl

F

52,391-7 Mol. Wt.C7H4Cl2O 175.01

5g

O

H

Cl

Cl

52,919-2 Mol. Wt.C7H3F3O 160.10

1mL5mL

O

H

F

F

F

54,331-4 Mol. Wt.C7H4FIO 250.01

1g

O

H

F

I

52,917-6 Mol. Wt.C7H3F3O 160.10

5mL

O

H

F

F

F

53,724-1 Mol. Wt.C7H4ClFO 158.56

1g5g

O

H

Cl

F

52,742-4 Mol. Wt.C7H5NO4 167.12

1g5g

O

H

OH

NO2

49,386-4 Mol. Wt.C7H6O4 154.12

1g

O

H

OHHO

HO

53,306-8 Mol. Wt.C7H7NO2 137.14

5g

N

O

H

O

52,918-4 Mol. Wt.C7H3F3O 160.10

1g5g

O

HF

F F

52,660-6 Mol. Wt.C7H4ClFO 158.56

1g5g

O

H

Cl

F

52,627-4 Mol. Wt.C7H5FO2 140.11

1g

O

H

OH

F

TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com

52,569-3 Mol. Wt.C6H4BrNO 186.01

1g10g

NBr

O

H

52,659-2 Mol. Wt.C7H3ClF2O 176.55

1g5g

O

H

Cl

F

F

51,830-1 Mol. Wt.C7H4FNO3 169.11

1g

O

H

NO2

F

51,677-5 Mol. Wt.C7H5BrO2 201.02

5g

O

H

Br

HO

52,887-0 Mol. Wt.C7H4BrFO 203.01

25g

O

HBr

F

52,663-0 Mol. Wt.C8H3ClF4O 226.56

1g5g

O

H

Cl

F

F3C

52,664-9 Mol. Wt.C8H3ClF4O 226.56

1g5g

O

H

Cl

F

CF3

52,897-8 Mol. Wt.C7H4BrFO 203.01

1g5g

O

HF

Br

52,921-4 Mol. Wt.C8H4F4O 192.10

1g5g

O

H

FF3C

52,914-1 Mol. Wt.C8H5F3OS 206.17

5g

O

H

SF3C

52,920-6 Mol. Wt.C8H4F4O 192.10

1g5g

O

HF3C

F

51,574-4 Mol. Wt.C8H6Br2O2 293.95

5g

O

H

O

Br

Br

52,916-8 Mol. Wt.C8H5F3O2 190.11

1g5g

O

H

O

CF3

52,922-2 Mol. Wt.C8H4F4O 192.10

1mL10mL

52,667-3 Mol. Wt.C11H8O2 172.18

1g5g

O

O

H

52,386-0 Mol. Wt.C11H12N2O 188.23

25g

O

H

N

CN

E540-9 Mol. Wt.C10H12O3 180.20

5g

O

H

O

O

51,804-2 Mol. Wt.C11H14O 162.23

5g

O

H

53,565-6 Mol. Wt.C11H8ClNO 205.64

1g

N

O

H

Cl

51,678-3 Mol. Wt.C11H14O3 194.23

5g

O

H

O

O

13,413-9 Mol. Wt.C10H9NO 159.19

1g5g

NH

O

H

53,564-8 Mol. Wt.C11H8ClNO 205.64

5g

N

O

H

Cl

51,630-9 Mol. Wt.C11H14O3 194.23

5g

O

H

OO

54,332-2 Mol. Wt.C15H11NO 221.26

1g5g

NH

O

H

51,112-9 Mol. Wt.C10H9NO 159.19

5g

N

O

H

49,399-6 Mol. Wt.C11H8ClNO2 221.65

5g

N

O

H

Cl

O

52,648-7 Mol. Wt.C12H10O 170.21

1g10g

OH

40,587-6 Mol. Wt.C15H12N2O2 252.27

1g5g

NNH

O

HO

52,645-2 Mol. Wt.C10H12O2 148.21

1g10g

O

H

51,640-6 Mol. Wt.C10H12O3 180.21

5g

53,308-4 Mol. Wt.C12H10O2 186.21

5g

O

H

O

49,974-9 Mol. Wt.C14H12O2 212.25

10mL50mL

O

H

O

52,338-0 Mol. Wt.C12H14OSi 202.33

5g

O

H

TMSi

54,981-9 Mol. Wt.C15H10FNO 239.24

1g5g

NH

O

H

F

TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com

49,387-2 Mol. Wt.C16H16O2 240.30

1g

O

H

O

51,577-9 Mol. Wt.C16H24O2 248.37

5g

O

H

O

52,665-7 Mol. Wt.C13H10O 182.22

5g

OH

54,333-0 Mol. Wt.C14H11BrO2 291.14

1g10g

O

H

O

Br

ArylaldehydesArylaldehydes

TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com

TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com

TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com

Arylaldehyde Resins for SPOS

Scavenger Resins5

for Aldehydes

References: (1) Wilson, T.W. et al. Tetrahedron Lett. 1997,38, 7151. (2) Sarantakis, D. et al. Tetrahedron Lett. 1997,38, 7325. (3) Bilodeau, M.T. et al. J. Org. Chem. 1998, 63,2800. (4) Estep, K.G. et al. J. Org. Chem. 1998, 63, 5300. (5) Kaldor, S.W. et al. Tetrahedron Lett. 1996, 40, 7193.

The following resins are useful for thesolid phase preparation of secondarysulfonamides, amides, ureas, and carbamates, and feature dilute-acid-labile linkers.1-4

Base resin

51,644-9AMEBA resin, 100-200 mesh, 1% cross-linked, 1.0-1.5 mmol/g

1g; 5g53,821-34-Benzyloxy-2,6-dimethoxybenz-aldehyde, polymer-bound, 100-200 mesh, 1% cross-linked

1g; 5g; 25g

51,627-93-Formyl-1-indoleacetic acid, polymer-bound

1g; 5g; 25g

53,240-1Formylpolystyrene, 100-200 mesh, 1% cross-linked, 0.7-1.5 mmol/g

1g; 5g; 25g

47,978-0Diethylenetriamine, polymer-bound, 2.5-3.0 mmol N/g

5g; 25g47,209-3Ethylenediamine, polymer-bound,1% cross-linked, 2.5-3.0 mmol N/g

5g; 25g

53,233-9p-Toluenesulfonyl hydrazide, polymer-bound, 1% cross-linked, 100-200 mesh, ~1.5 mmol N/g

1g; 5g; 25g

Please call us at 800-336-9719 (USA) or 314-534-4900, contact your localSigma-Aldrich office, or visit us at

www.sigma-aldrich.com/safc.

Sigma-Aldrich Fine Chemicals is readyto provide a competitive bulk quote

on any of our products includingthose listed in this publication.

✔ Prompt delivery of the broadestrange of chemicals from stock.

✔ Extensive custom processdevelopment and scaleup.

✔ New large scale & cGMP manufacturing facilities worldwide.

✔ Custom packaging.

✔ Analytical services & regulatory support.

We offer:

Name _____________________________________________________________

Company __________________________________________________________

Department____________________________ Mail Stop__________________

Address _______________________________________ Bldg/Rm # _________

City_______________ State____ Country___________ Postal Code________

Phone________________ Fax _________________ E-mail_________________

Tell Us About YourselfTell Us About Yourself

A reagent thatturns aldehydespurple!

Purpald®

References: (1) Hopps, H.B. Aldrichimica Acta 2000, 33, 28. (2) Dickinson, R.G.; Jacobsen, N.W. Chem Commun. 1970, 1719.Purpald is a registered trademark of Sigma-Aldrich Co.

O

H

F

F3C

O

H

O

O

H

O

O

The emerging importance of combinatorial and high-throughput methods in chemistryhas resulted in a need for specialized kits of chemicals. We are able to provide a variety of these kits by combining Aldrich’s vast chemical inventory and our customizedweighing process. Some of our more popular kits have included carboxylic acids, arylboronic acids, amines, and alcohols, and we are now pleased to add isocyanates tothis list. Please contact us. We can create a kit tailored to your specific requirements.

Key Features Include:Flexibility

❖ Ideal for high-throughput or combinatorial chemistry; available in vials or titerplates

No Minimum Order❖ Service as diverse as your needs

Reduces Waste❖ Little or no unused product to store or dispose

Saves Time❖ Less time weighing reagents, more time doing research

For more information on this unique service, please call us at800-333-7306 (USA) or e-mail us at [email protected].

In Europe, e-mail us at [email protected].

Aldrich Offers CombiKits™

CombiKits™ is a trademark of Sigma-Aldrich Co.

CGM

For a complete listing of all of our arylaldehydes, please visit our Web site at www.sigma-aldrich.com/aldrich, go to the Organics area, and click on Specialty Areas; or contact our Technical Services department by phone, 800-231-8327 (USA),

fax, 414-287-4079, or e-mail, [email protected]. As always, new product suggestions are welcome and appreciated.

Essential Tools for Today’s Synthetic Chemist

Page 6: Arylaldehydes - Sigma-Aldrich

Arylaldehydes

54,264-4 Mol. Wt.C8H7FO2 154.14

1g5g

O

H

F

O

52,681-9 Mol. Wt.C8H7FO3 170.14

1g

O

HO

F

HO

51,513-2 Mol. Wt.C8H7FO 138.14

5g

O

H

F

51,832-8 Mol. Wt.C8H7NO3 165.15

1g

O

H

NO2

52,898-6 Mol. Wt.C8H7FO2 154.14

25g

O

H

O F

51,576-0 Mol. Wt.C8H7NO4 181.15

5g

O

H

O

O2N

52,662-2 Mol. Wt.C8H6ClFO 172.58

1g5g

O

H

F

Cl

53,673-3 Mol. Wt.C8H7FO2 154.14

1g5g

O

H

F

O

51,642-2 Mol. Wt.C8H7NO4 181.15

5g

O

H

O

NO2

51,383-0 Mol. Wt.C9H7NO 145.16

5g

NH

O

H

52,661-4 Mol. Wt.C8H6ClFO 172.58

1g5g

O

H

Cl

F

52,310-0 Mol. Wt.C8H7FO2 154.14

1g5g

O

H

O

F

52,311-9 Mol. Wt.C8H8OS 152.22

5g

O

H

S

52,306-2 Mol. Wt.C9H8O 132.16

5g

O

H

52,923-0 Mol. Wt.C8H6F2O2 172.12

5g

O

H

OCF2H

52,314-3 Mol. Wt.C8H7FO 138.14

5g

O

H

F

51,286-9 Mol. Wt.C8H9BO4 179.97

5g25g

O

H

B(OH)2

O

51,874-3 Mol. Wt.C9H6BrNO 224.06

5g

NH

O

HBr

34,854-6 Mol. Wt.C9H9FO3 184.16

1g

O

H

O

O

F

51,806-9 Mol. Wt.C9H10O 134.18

1g5g

O

H

51,805-0 Mol. Wt.

C9H10O 134.18

5g

O

H

52,640-1 Mol. Wt.C9H4F6O 242.12

1g5g

O

H

CF3F3C

53,307-6 Mol. Wt.C9H6ClNO 179.60

5g

NH

O

HCl

51,575-2 Mol. Wt.C9H9BrO2 229.08

5g

O

H

O

Br

TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com

51,515-9 Mol. Wt.C9H10O 134.18

5g

O

H

51,535-3 Mol. Wt.C9H10O 134.18

1g5g

O

H

49,385-6 Mol. Wt.C9H10O 134.18

1g5g

O

H

54,382-9 Mol. Wt.C10H4FNO5 237.14

1g

O

O

H

O

F

NO2

51,631-7 Mol. Wt.C9H10O2 150.18

1g5g

O

H

O

54,372-1 Mol. Wt.C10H6ClFO2 212.60

1g

O

O

H

Cl

F

54,362-4 Mol. Wt.C10H5FO3 192.15

1g

O

O

H

O

F

51,632-5 Mol. Wt.C9H10O2 150.18

5g

Arylaldehyde chemistry has led to a wealth of diverse products, so naturally Aldrich is determined to offer thewidest possible breadth of substitution patterns. Target molecules prepared from groups of arylaldehydes haveincluded aminoindenes,1 quinolines,2 arylglycines,3 and homoallylic alcohols.4 With over 400 arylaldehydes amongthe more than 80,000 products in stock at Sigma-Aldrich, chances are you’ll find what you’re looking for!

(1) Katritzky, A. R. et al. J. Org. Chem. 2000, 65, 8066. (2) Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1996, 118, 8977. (3) Beller, M. et al. J. Org. Chem. 1998, 63,5658. (4) Curran, D.P.; Zhiyong, L. Med. Chem. Res. 1998, 8, 261. 1. What type of chemistry do you routinely perform?

❍ General Organic Chemistry [ORGS] ❍ Organometallics [ORGM]❍ Organic Combinatorial [COCH] ❍ Polymer Chemistry [POLY]❍ Chiral Chemistry [CHIR] ❍ Drug Discovery [DRUG]

2. Please check any of the following FREE catalog and literature piecesthat you would like to receive.❍ Aldrich Handbook [002]❍ Sigma General Catalog [001]❍ Fluka/Riedel-de-Haën® Catalog [003]❍ Aldrichimica Acta [032]❍ Resins for Combichem [DLW]❍ Combikits™/Small Sample Service [CBJ]❍ Polymer Products CD [DGQ]❍ New Fluorinated Products [DEO]❍ Products for Suzuki Coupling [DTK]

3. What other specialized grouping would be of interest to you?❍ Oxidizing agents [3AA] ❍ Terminal alkenes [3AE]❍ Reducing agents [3AB] ❍ Sulfonyl chlorides [3AF]❍ Oximes [3AC] ❍ Nitriles [3AG]❍ Terminal alkynes [3AD] ❍ Other _____________________

4. ❍ I would like to receive a FREE CD-ROM with product listingsfrom the Sigma-Aldrich Library of Rare Chemicals. [DDH]

Fluka/Riedel-de-Haën and Combikits are a registered trademark and trademark, respectively, of Sigma-Aldrich Co.

Purpald®, an aminotriazole, continues to be useful as a complexation reagent for the spectrophotomeric determination of aldehydes, e.g., in drug concentrationanalyses and in determining airborne formaldehyde.Ketones, esters, formic acid, amides, hydroxylamines,quinones, uric acid, hydrazines and aminophenols do not react with Purpald® to yield purple products.1-2

For properties, procedure for detecting aldehydes, applications, and references of Purpald®, please contact our Technical Services department at 800-231-8327(USA)or your local office and request Aldrich Technical Bulletin#AL-145; or visit our Web site, www.sigma-aldrich.com/aldrichand click on Technical Bulletins.

16,289-2 Purpald®, 99+%(4-amino-3-hydrazino-5-mercapto-1,2,4-triazole)

5g; 25g; 100g

53,145-6 Mol. Wt.C5H3ClO2 130.53

1g

OCl

O

H

49,990-0 Mol. Wt.C5H5BO3S 155.97

1g5g

S

O

H

B(OH)2

51,405-5 Mol. Wt.C5H5BO3S 155.97

1g5g

S(HO)2B

H

O

49,991-9 Mol. Wt.C5H5BO3S 155.97

1g5g

S

O

H

B(OH)2

52,642-8 Mol. Wt.C7H3ClF2O 176.55

1g5g

O

H

F

Cl

F

52,391-7 Mol. Wt.C7H4Cl2O 175.01

5g

O

H

Cl

Cl

52,919-2 Mol. Wt.C7H3F3O 160.10

1mL5mL

O

H

F

F

F

54,331-4 Mol. Wt.C7H4FIO 250.01

1g

O

H

F

I

52,917-6 Mol. Wt.C7H3F3O 160.10

5mL

O

H

F

F

F

53,724-1 Mol. Wt.C7H4ClFO 158.56

1g5g

O

H

Cl

F

52,742-4 Mol. Wt.C7H5NO4 167.12

1g5g

O

H

OH

NO2

49,386-4 Mol. Wt.C7H6O4 154.12

1g

O

H

OHHO

HO

53,306-8 Mol. Wt.C7H7NO2 137.14

5g

N

O

H

O

52,918-4 Mol. Wt.C7H3F3O 160.10

1g5g

O

HF

F F

52,660-6 Mol. Wt.C7H4ClFO 158.56

1g5g

O

H

Cl

F

52,627-4 Mol. Wt.C7H5FO2 140.11

1g

O

H

OH

F

TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com

52,569-3 Mol. Wt.C6H4BrNO 186.01

1g10g

NBr

O

H

52,659-2 Mol. Wt.C7H3ClF2O 176.55

1g5g

O

H

Cl

F

F

51,830-1 Mol. Wt.C7H4FNO3 169.11

1g

O

H

NO2

F

51,677-5 Mol. Wt.C7H5BrO2 201.02

5g

O

H

Br

HO

52,887-0 Mol. Wt.C7H4BrFO 203.01

25g

O

HBr

F

52,663-0 Mol. Wt.C8H3ClF4O 226.56

1g5g

O

H

Cl

F

F3C

52,664-9 Mol. Wt.C8H3ClF4O 226.56

1g5g

O

H

Cl

F

CF3

52,897-8 Mol. Wt.C7H4BrFO 203.01

1g5g

O

HF

Br

52,921-4 Mol. Wt.C8H4F4O 192.10

1g5g

O

H

FF3C

52,914-1 Mol. Wt.C8H5F3OS 206.17

5g

O

H

SF3C

52,920-6 Mol. Wt.C8H4F4O 192.10

1g5g

O

HF3C

F

51,574-4 Mol. Wt.C8H6Br2O2 293.95

5g

O

H

O

Br

Br

52,916-8 Mol. Wt.C8H5F3O2 190.11

1g5g

O

H

O

CF3

52,922-2 Mol. Wt.C8H4F4O 192.10

1mL10mL

52,667-3 Mol. Wt.C11H8O2 172.18

1g5g

O

O

H

52,386-0 Mol. Wt.C11H12N2O 188.23

25g

O

H

N

CN

E540-9 Mol. Wt.C10H12O3 180.20

5g

O

H

O

O

51,804-2 Mol. Wt.C11H14O 162.23

5g

O

H

53,565-6 Mol. Wt.C11H8ClNO 205.64

1g

N

O

H

Cl

51,678-3 Mol. Wt.C11H14O3 194.23

5g

O

H

O

O

13,413-9 Mol. Wt.C10H9NO 159.19

1g5g

NH

O

H

53,564-8 Mol. Wt.C11H8ClNO 205.64

5g

N

O

H

Cl

51,630-9 Mol. Wt.C11H14O3 194.23

5g

O

H

OO

54,332-2 Mol. Wt.C15H11NO 221.26

1g5g

NH

O

H

51,112-9 Mol. Wt.C10H9NO 159.19

5g

N

O

H

49,399-6 Mol. Wt.C11H8ClNO2 221.65

5g

N

O

H

Cl

O

52,648-7 Mol. Wt.C12H10O 170.21

1g10g

OH

40,587-6 Mol. Wt.C15H12N2O2 252.27

1g5g

NNH

O

HO

52,645-2 Mol. Wt.C10H12O2 148.21

1g10g

O

H

51,640-6 Mol. Wt.C10H12O3 180.21

5g

53,308-4 Mol. Wt.C12H10O2 186.21

5g

O

H

O

49,974-9 Mol. Wt.C14H12O2 212.25

10mL50mL

O

H

O

52,338-0 Mol. Wt.C12H14OSi 202.33

5g

O

H

TMSi

54,981-9 Mol. Wt.C15H10FNO 239.24

1g5g

NH

O

H

F

TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com

49,387-2 Mol. Wt.C16H16O2 240.30

1g

O

H

O

51,577-9 Mol. Wt.C16H24O2 248.37

5g

O

H

O

52,665-7 Mol. Wt.C13H10O 182.22

5g

OH

54,333-0 Mol. Wt.C14H11BrO2 291.14

1g10g

O

H

O

Br

ArylaldehydesArylaldehydes

TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com

TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com

TO ORDER: CONTACT YOUR LOCAL SIGMA-ALDRICH OFFICE OR CALL 1-800-558-9160 (USA) or visit our Web site at www.sigma-aldrich.com

Arylaldehyde Resins for SPOS

Scavenger Resins5

for Aldehydes

References: (1) Wilson, T.W. et al. Tetrahedron Lett. 1997,38, 7151. (2) Sarantakis, D. et al. Tetrahedron Lett. 1997,38, 7325. (3) Bilodeau, M.T. et al. J. Org. Chem. 1998, 63,2800. (4) Estep, K.G. et al. J. Org. Chem. 1998, 63, 5300. (5) Kaldor, S.W. et al. Tetrahedron Lett. 1996, 40, 7193.

The following resins are useful for thesolid phase preparation of secondarysulfonamides, amides, ureas, and carbamates, and feature dilute-acid-labile linkers.1-4

Base resin

51,644-9AMEBA resin, 100-200 mesh, 1% cross-linked, 1.0-1.5 mmol/g

1g; 5g53,821-34-Benzyloxy-2,6-dimethoxybenz-aldehyde, polymer-bound, 100-200 mesh, 1% cross-linked

1g; 5g; 25g

51,627-93-Formyl-1-indoleacetic acid, polymer-bound

1g; 5g; 25g

53,240-1Formylpolystyrene, 100-200 mesh, 1% cross-linked, 0.7-1.5 mmol/g

1g; 5g; 25g

47,978-0Diethylenetriamine, polymer-bound, 2.5-3.0 mmol N/g

5g; 25g47,209-3Ethylenediamine, polymer-bound,1% cross-linked, 2.5-3.0 mmol N/g

5g; 25g

53,233-9p-Toluenesulfonyl hydrazide, polymer-bound, 1% cross-linked, 100-200 mesh, ~1.5 mmol N/g

1g; 5g; 25g

Please call us at 800-336-9719 (USA) or 314-534-4900, contact your localSigma-Aldrich office, or visit us at

www.sigma-aldrich.com/safc.

Sigma-Aldrich Fine Chemicals is readyto provide a competitive bulk quote

on any of our products includingthose listed in this publication.

✔ Prompt delivery of the broadestrange of chemicals from stock.

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A reagent thatturns aldehydespurple!

Purpald®

References: (1) Hopps, H.B. Aldrichimica Acta 2000, 33, 28. (2) Dickinson, R.G.; Jacobsen, N.W. Chem Commun. 1970, 1719.Purpald is a registered trademark of Sigma-Aldrich Co.

O

H

F

F3C

O

H

O

O

H

O

O

The emerging importance of combinatorial and high-throughput methods in chemistryhas resulted in a need for specialized kits of chemicals. We are able to provide a variety of these kits by combining Aldrich’s vast chemical inventory and our customizedweighing process. Some of our more popular kits have included carboxylic acids, arylboronic acids, amines, and alcohols, and we are now pleased to add isocyanates tothis list. Please contact us. We can create a kit tailored to your specific requirements.

Key Features Include:Flexibility

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For more information on this unique service, please call us at800-333-7306 (USA) or e-mail us at [email protected].

In Europe, e-mail us at [email protected].

Aldrich Offers CombiKits™

CombiKits™ is a trademark of Sigma-Aldrich Co.

CGM

For a complete listing of all of our arylaldehydes, please visit our Web site at www.sigma-aldrich.com/aldrich, go to the Organics area, and click on Specialty Areas; or contact our Technical Services department by phone, 800-231-8327 (USA),

fax, 414-287-4079, or e-mail, [email protected]. As always, new product suggestions are welcome and appreciated.

Essential Tools for Today’s Synthetic Chemist

Page 7: Arylaldehydes - Sigma-Aldrich

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NewArylaldehydes

Global Bulk

Manufacturing

Combikits™

(Vials or

Titerplates)

Arylaldehyde

Resins

for SPOS

Over 80 New

Products!

Organic SynthesisBuilding Blocks for

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ChemFiles Vol. 1, No. 2 • 2001Dess–Martin Periodinane

is widely used for the mild

oxidation of alcohols to

aldehydes and ketones.1

This reagent is especially useful

for substrates containing sensitive

functional groups and offers an

alternative to other mild

reagents (e.g. TPAP). Other

advantages such as selectivity,

rapid rates, avoiding the use of

toxic (i.e. chromium-based)

chemicals, using stoichiometric

amounts of reagent, and ease of

work up make the Dess–Martin

periodinane a reliable and easy-to-

use oxidizer in organic synthesis.

Dess–Martin PeriodinaneDess–Martin Periodinane

1. Useful in the preparation of epimerization-sensitive optically active N-protected α-amino aldehydes with high enantiomeric excess.2

2. Oximes and tosylhydrazones are converted to their corresponding carbonyl compounds under mild conditionswithout overoxidation of the final product.3

3. Oxidation of sugar hydroxyls in good yields with periodinane avoids the use of ruthenium dioxide.4

4. A highly unstable dialdehyde was prepared by oxidation with periodinane and trapped in situ with a pre-formed Wittig ylide.5

5. A convenient route to the preparation of highly reactive acyl nitroso compounds. These products can be trapped by dienes to form cycloadducts.6

6. Rapid production of complex and diverse natural product-like polycycles. A proposed mechanism starts with an ortho-oxidation followed by an intramolecular hetero Diels–Alder reaction.7

7. Neutral and mild work-up conditions avoid the formation of dehydrofluorinated by-products in the oxidation of polyfluorinated primary alcohols to aldehydes.8

27,462-3 Dess-Martin periodinane, 97% 1g; 5g[1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one]

Preparation of ArylaldehydesPreparation of ArylaldehydesVarious routes are available for the formation of arylaldehydes, including classical aromatic formylation viaVilsmeier, Gatterman, or Reimer–Tiemann reactions. Other methods include reduction of carboxylic acid derivatives,especially the reduction of esters with DIBAH9, and the oxidation of alcohols, typically with chromium reagents but accomplished under mild conditions with TPAP10 or Dess-Martin periodinane (see above).

33,074-4 Tetrapropylammonium perruthenate, 97% (TPAP) 250mg; 1g25,681-1 Diisobutylaluminum hydride (DIBAH) 100g; 1kg19,014-4 Pyridinium chlorochromate, 98% (PCC) 25g; 100g; 500g21,469-8 Pyridinium dichromate, 98% (PDC) 5g; 100g 500g

References: (1) Dess, D.B; Martin, J. C. J. Org. Chem. 1983, 48, 4155. (2) Myers, A.G. et al. Tetrahedron Lett. 2000, 41, 1359. (3) Bose, D.S.; Narsaiah, A. V. Synth. Commun.1999, 29, 937. (4) Rao, H. S. P. et al. Indian J. Chem., Sect. B. 1997, 36B, 816. (5) Barrett, A. G.M. et al. J. Org. Chem. 1997, 62, 9376. (6) Jenkins, N. E. et al. Synth. Commun.2000, 30, 947. (7) Nicolaou, K.C. et al. Angew. Chem., Int. Ed. Engl. 2000, 39, 622. (8) Lévêque, L. et al. Tetrahedron Lett. 1998. 39, 8857. (9) Winterfeldt, E. Synthesis1975, 617. (10) Ley, S.V. et al. ibid. 1994, 639.

Page 8: Arylaldehydes - Sigma-Aldrich

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ChemFiles Vol. 1, No. 2 • 2001Dess–Martin Periodinane

is widely used for the mild

oxidation of alcohols to

aldehydes and ketones.1

This reagent is especially useful

for substrates containing sensitive

functional groups and offers an

alternative to other mild

reagents (e.g. TPAP). Other

advantages such as selectivity,

rapid rates, avoiding the use of

toxic (i.e. chromium-based)

chemicals, using stoichiometric

amounts of reagent, and ease of

work up make the Dess–Martin

periodinane a reliable and easy-to-

use oxidizer in organic synthesis.

Dess–Martin PeriodinaneDess–Martin Periodinane

1. Useful in the preparation of epimerization-sensitive optically active N-protected α-amino aldehydes with high enantiomeric excess.2

2. Oximes and tosylhydrazones are converted to their corresponding carbonyl compounds under mild conditionswithout overoxidation of the final product.3

3. Oxidation of sugar hydroxyls in good yields with periodinane avoids the use of ruthenium dioxide.4

4. A highly unstable dialdehyde was prepared by oxidation with periodinane and trapped in situ with a pre-formed Wittig ylide.5

5. A convenient route to the preparation of highly reactive acyl nitroso compounds. These products can be trapped by dienes to form cycloadducts.6

6. Rapid production of complex and diverse natural product-like polycycles. A proposed mechanism starts with an ortho-oxidation followed by an intramolecular hetero Diels–Alder reaction.7

7. Neutral and mild work-up conditions avoid the formation of dehydrofluorinated by-products in the oxidation of polyfluorinated primary alcohols to aldehydes.8

27,462-3 Dess-Martin periodinane, 97% 1g; 5g[1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one]

Preparation of ArylaldehydesPreparation of ArylaldehydesVarious routes are available for the formation of arylaldehydes, including classical aromatic formylation viaVilsmeier, Gatterman, or Reimer–Tiemann reactions. Other methods include reduction of carboxylic acid derivatives,especially the reduction of esters with DIBAH9, and the oxidation of alcohols, typically with chromium reagents but accomplished under mild conditions with TPAP10 or Dess-Martin periodinane (see above).

33,074-4 Tetrapropylammonium perruthenate, 97% (TPAP) 250mg; 1g25,681-1 Diisobutylaluminum hydride (DIBAH) 100g; 1kg19,014-4 Pyridinium chlorochromate, 98% (PCC) 25g; 100g; 500g21,469-8 Pyridinium dichromate, 98% (PDC) 5g; 100g 500g

References: (1) Dess, D.B; Martin, J. C. J. Org. Chem. 1983, 48, 4155. (2) Myers, A.G. et al. Tetrahedron Lett. 2000, 41, 1359. (3) Bose, D.S.; Narsaiah, A. V. Synth. Commun.1999, 29, 937. (4) Rao, H. S. P. et al. Indian J. Chem., Sect. B. 1997, 36B, 816. (5) Barrett, A. G.M. et al. J. Org. Chem. 1997, 62, 9376. (6) Jenkins, N. E. et al. Synth. Commun.2000, 30, 947. (7) Nicolaou, K.C. et al. Angew. Chem., Int. Ed. Engl. 2000, 39, 622. (8) Lévêque, L. et al. Tetrahedron Lett. 1998. 39, 8857. (9) Winterfeldt, E. Synthesis1975, 617. (10) Ley, S.V. et al. ibid. 1994, 639.