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Supplementary information: General synthesis for the preparation of 1-substituted 1H-tetrazoles A mixture of amine (1 mmol), sodium azide (1 mmol), triethyl orthoformate (1.2 mmol) and Fe 3 O 4 @silica sulfonic acid (0.02 g) was taken in a round-bottomed flask and stirred at 100 °C. The progress of the reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, the reaction mixture was cooled to room temperature and diluted with ethyl acetate (3×20 mL). The catalyst was removed by an external magnet, and then the resulting solution was washed with water and dried over anhydrous Na 2 SO 4 . After concentration, a crystallization step was performed using EtOAc- hexane (1:9). The products were characterized by 1 H NMR, 13 C NMR, FT-IR and melting points. We have reported the spectral data of synthesized compounds. 1-(phenyl)-1H-tetrazole Yellow solid; m.p=: 63-65 °C M.P Lit : 65-67 °C IR (KBr)/ A (cm -1 ): 3126 (C-H, sp 2 stretch Ar), 1694 (C=N), 1597, 1498 (C=C); 1 H NMR (CDCl 3 , 400 MHz) (ppm): 7.07-7.34 (m, 5H, Ar), 8.20 (s, 1H tetrazole). 1-(4-Boromophenyl)-1H-tetrazole White solid; m.p=169-170°C N N N N N N N N Br Electronic Supplementary Material (ESI) for Dalton Transactions. This journal is © The Royal Society of Chemistry 2014

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  • 1

    Supplementary information:

    General synthesis for the preparation of 1-substituted 1H-tetrazoles

    A mixture of amine (1 mmol), sodium azide (1 mmol), triethyl orthoformate (1.2

    mmol) and Fe3O4@silica sulfonic acid (0.02 g) was taken in a round-bottomed flask and

    stirred at 100 °C. The progress of the reaction was monitored by thin layer chromatography

    (TLC). After completion of the reaction, the reaction mixture was cooled to room

    temperature and diluted with ethyl acetate (3×20 mL). The catalyst was removed by an

    external magnet, and then the resulting solution was washed with water and dried over

    anhydrous Na2SO4. After concentration, a crystallization step was performed using EtOAc-

    hexane (1:9). The products were characterized by 1H NMR, 13C NMR, FT-IR and melting

    points. We have reported the spectral data of synthesized compounds.

    1-(phenyl)-1H-tetrazole

    Yellow solid; m.p=: 63-65 °C M.PLit: 65-67 °C

    IR (KBr)/ ν (cm-1): 3126 (C-H, sp2 stretch Ar), 1694 (C=N), 1597, 1498 (C=C); 1H NMR

    (CDCl3, 400 MHz) δ (ppm): 7.07-7.34 (m, 5H, Ar), 8.20 (s, 1H tetrazole).

    1-(4-Boromophenyl)-1H-tetrazole

    White solid; m.p=169-170°C

    N

    NN

    N

    N

    NN

    NBr

    Electronic Supplementary Material (ESI) for Dalton Transactions.This journal is © The Royal Society of Chemistry 2014

  • 2

    IR (KBr)/ ν (cm-1): 3060 (C-H, sp2 stretch, Ar), 1659 (C=N), 1576, 1482 (C=C); 1H NMR

    (CDCl3, 400 MHz) δ (ppm): 6.92-6.94 (d, 2H), 7.40-7.42 (d, 2H), 8.09 (s, 1H tetrazole); 13C

    NMR (CDCl3, 100 MHz) δ (ppm)): 116.43, 120.76, 132.03, 143.99, 149.29.

    1-(4-Chlorophenyl)-1H-tetrazole

    White solid; m.p=153-155 °C M.PLit:155-156 °C

    IR (KBr)/ ν (cm-1): 3057 (C-H, sp2 stretch, Ar), 1661 (C=N), 1485, 1581 (C=C) 1H NMR

    (CDCl3, 400 MHz) δ (ppm): 6.98-7.00 (d-2H), 7.27-7.29 (d-2H), 8.09 (s-1H tetrazole); 13C

    NMR (CDCl3, 100 MHz) δ (ppm)): 120.35, 128.85, 129.47, 143.52, 149.50.

    1-(4-Methylphenyl)-1H-tetrazole

    Light yellow solid; m.p=92-99 °C

    IR (KBr)/ ν (cm-1): 3022 (C-H, sp2 stretch, Ar), 2918(C-H, sp3 stretch), 1664 (C=N), 1607,

    1506 (C=C); 1H NMR (CDCl3, 400 MHz) δ (ppm): 2.34 (s, 3H), 6.94-6.96 (d, 2H), 7.11-7.13

    (d, 2H), 8.17 (s, 1H tetrazole); 13C NMR (CDCl3, 100 MHz) δ (ppm)): 20.79, 119.08, 129.63,

    130.17, 142.95, 149.77.

    N

    NN

    NMe

    N

    NN

    NCl

  • 3

    1-(3-Methylphenyl)-1H-tetrazole

    White solid; m.p=53-55 °C

    IR (KBr)/ ν (cm-1): 3167 (C-H, sp2 stretch, Ar), 2923 (C-H, sp3 stretch), 1690 (C=N), 1594,

    1483 (C=C); 1H NMR (CDCl3, 400 MHz) δ (ppm): 2.33 (s, 3H), 6.86 (s, 1H), 6.89- 6.91 (d,

    2H), 7.18-7.22(t, 1H), 8.21 (s, 1H tetrazole); 13C NMR (CDCl3, 100 MHz) δ (ppm) ): 21.43,

    115.93, 119.97, 124.06, 129.19, 139.26, 145.28, 149.23

    1-(2-Methylphenyl)-1H-tetrazole

    White solid; m.p=152-155 °C

    IR (KBr)/ ν (cm-1): 3015 (C-H, sp2 stretch, Ar), 2870 (C-H, sp3 stretch), 1664(C=N), 1488,

    1590 (C=C); 1H NMR (CDCl3, 400 MHz) δ (ppm): 2.33 (s, 3H), 7.02-7.03 (d, 1H), 7.05-7.07

    (d, 1H), 7.18-7.22 (t, 2H), 8.08 (s, 1HTetrazole); 13C NMR (CDCl3, 100 MHz) δ (ppm)):

    17.94, 117.68, 123.43, 127, 128.71, 130.72, 144.10, 147.78.

    1-(2,4-Dimethylphenyl)-1H-tetrazole

    White solid; m.p=133-135 °C

    N

    NN

    N

    Me

    N

    NN

    N

    Me

    N

    NN

    NMe

    Me

  • 4

    IR (KBr)/ ν (cm-1): 3069 (C-H, sp2 stretch, Ar), 2914 (C-H, sp3 stretch), 1663 (C=N), 1495,

    1607 (C=C); 1H NMR (CDCl3, 400 MHz) δ (ppm): 2.29 (s, 3H), 2.30 (s, 3H), 6.94-6.96 (d,

    1H), ), 6.98-7.00 (d, 1H), 7.02 (s, 1H), 8.00 (s, 1H tetrazole).

    1-(4-Acetylphenyl)-1H-tetrazole

    Yellow solid; m.p=175-176 °C

    IR (KBr)/ ν (cm-1): 3075 (C-H, sp2 stretch, Ar), 2995 (C-H, sp3 stretch), 1669 (C=N), 1499,

    1585 (C=C); 1H NMR (CDCl3, 400 MHz) δ (ppm): 2.60 (S, 3H), 7.13-7.15 (d, 2H), 7.95-7.97

    (d, 2H), 8.30 (s, 1H tetrazole).

    1-(3-Chlorophenyl)-1H-tetrazole

    White solid; m.p=137-139 °C

    IR (KBr)/ ν (cm-1): 3065 (C-H, sp2 stretch, Ar), 1669 (C=N), 1473, 1586 (C=C). 1H NMR

    (CDCl3, 400 MHz) δ (ppm): 6.92-6.94 (d, 1H) 7.07-7.09 (d, 2H) 7.26-7.27 (t, 1H), 8.14 (s-1H

    tetrazole); 13C NMR (CDCl3, 100 MHz) δ (ppm)): 117.45, 119.23, 123.73, 130.34, 135.12,

    146.14, 149.72.

    1-(2-Chlorophenyl)-1H-tetrazole

    N

    NN

    NO

    N

    NN

    N

    Cl

    N

    NN

    N

    Cl

  • 5

    White solid; m.p=129-131 °C

    IR (KBr)/ ν (cm-1): 3023 (C-H, sp2 stretch, Ar), 1670 (C=N), 1481, 1598 (C=C); 1H NMR

    (CDCl3, 400 MHz) δ (ppm): 7.03-7.50 (m-4H), 8.10 (s-1H tetrazole).

    1-(naphthalene-1-yl)-1H-tetrazole

    White solid; m.p=132-135 °C

    IR (KBr)/ ν (cm-1): 3048 (C-H, sp2 stretch, Ar), 1658(C=N), 1574, 1432 (C=C); 1H NMR

    (CDCl3, 400 MHz) δ (ppm): 7.23-8.27 (m, 7H), 8.36 (s, 1H tetrazole).

    1-[2-(1H-tetrazol-1-yl) phenyl]-1H-tetrazole

    White solid; m.p=167-169 °C

    N

    N

    N N

    N

    N N

    N

    N

    NN

    N

  • 6

    IR (KBr)/ ν (cm-1): 3062 (C-H, sp2 stretch, Ar), 1619 (C=N) 1458, 1588 (C=C); 1H NMR

    (CDCl3, 400 MHz) δ (ppm): 7.30-7.70 (m, 4H), 8.11 (s, 1HTetrazole); 13C NMR (CDCl3, 100

    MHz) δ (ppm): 115.76, 122.37, 138.50, 142.40.

  • 7

    N

    N

    N N

  • 8

    N

    NN

    N

    Cl

  • 9

    N

    NN

    N

    Me

  • 10

    N

    NN

    N

    Me

  • 11

    N

    NN

    NMe

    Me

  • 12

    N

    NN

    NBr

  • 13

    N

    NN

    NBr

  • 14

    N

    N N

    N

    N

    NN

    N

  • 15

    N

    N N

    N

    N

    NN

    N

  • 16

    N

    NN

    N

    Cl

  • 17

    N

    NN

    N

    Cl

  • 18

    N

    NN

    NCl

  • 19

    N

    NN

    NCl

  • 20

    N

    NN

    NO

  • 21

    N

    NN

    N

  • 22

    N

    NN

    N

    Me

  • 23

    N

    NN

    N

    Me

  • 24

    N

    NN

    NMe

  • 25

    N

    NN

    NMe


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