2-bromo-1-(bromomethyl)-4-nitrobenzene Chemical Properties

Melting point:

73-74°

Boiling point:

348.0±27.0 °C(Predicted)

Density 

2.006±0.06 g/cm3(Predicted)

storage temp. 

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

Appearance

White to off-white Solid

Safety Information

HazardClass 

IRRITANT

HS Code 

2916399090

2-bromo-1-(bromomethyl)-4-nitrobenzene Usage And Synthesis

Synthesis

General procedure for the synthesis of 2-bromo-4-nitrobenzyl bromide from m-bromonitrobenzene: A mixture of 2-bromo-6-nitrobenzene (1.08 g, 5.00 mmol) and N-bromosuccinimide (908 mg, 5.10 mmol) was dissolved in carbon tetrachloride (15 mL), and α,α'-azobisisobutyronitrile (AIBN) (28 mg) was added as initiator. The reaction mixture was stirred at 70 °C for 3 hours. Subsequently, additional AIBN (82 mg) was added in batches at the same temperature and stirring was continued for 4 hours. After completion of the reaction, the reaction mixture was diluted with chloroform and filtered to remove the precipitate. The filtrate was distilled under reduced pressure to remove the solvent and the crude product obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=1/1) to afford the target compound 2-bromo-1-(bromomethyl)-4-nitrobenzene (493 mg, 33% yield). The product was characterized by 1H-NMR (CDCl3): δ 4.62 (2H, s), 7.65 (1H, d, J=8.4Hz), 8.17 (1H, dd, J=8.4,2.2Hz), 8.46 (1H, d, J=2.2Hz).

References

[1] Patent: EP1844768, 2007, A1. Location in patent: Page/Page column 39

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