4-BROMO-2-NITROBENZYL BROMIDE Chemical Properties

Boiling point:

325.8±27.0 °C(Predicted)

Density 

2.006±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

solid

color 

Light Yellow

Safety Information

HS Code 

2904990090

4-BROMO-2-NITROBENZYL BROMIDE Usage And Synthesis

Synthesis

General procedure for the synthesis of 4-bromo-2-nitrobenzyl bromide from 4-bromo-2-nitrotoluene: (1) Preparation of 4-bromo-1-(bromomethyl)-2-nitrobenzene (0145): 4-bromo-2-nitrotoluene (25.0 g, 116 mmol), N-bromosuccinimide (28.2 g, 162 mmol) and 2 ,2'-azobis(2-methylpropionitrile) (1.90 mg, 11.6 mmol) and the reaction mixture was refluxed for 18 hours. After completion of the reaction, the reaction solution was filtered and the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (ethyl acetate/hexane = 1/9) to afford 18.5 g (54% yield) of 4-bromo-2-nitrobenzyl bromide.1H-NMR (CDCl3) data: δ 4.78 (s, 2H, CH2), 7.46 (d, J = 8.0 Hz, 1H, Ar-H), 7.74 (dd, J = 2.0, 8.1 Hz, 1H, Ar-H), 8.18 (d, J = 1.7 Hz, 1H, Ar-H).

References

[1] Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 401 - 406
[2] Organic Letters, 2012, vol. 14, # 15, p. 3870 - 3873
[3] Patent: EP2907818, 2015, A1. Location in patent: Paragraph 0145
[4] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 20, p. 6574 - 6595
[5] Heterocycles, 1994, vol. 39, # 2, p. 767 - 778

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