4-Bromo-2-nitrobenzyl bromide

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4-Bromo-2-nitrobenzyl bromide Basic information
Product Name:4-Bromo-2-nitrobenzyl bromide
Synonyms:Benzene, 4-broMo-1-(broMoMethyl)-2-nitro-;4-bromo-1-(bromomethyl)-2-nitrobenzene;4-Bromo-2-nitrobenzyl bromide
CAS:82420-34-6
MF:C7H5Br2NO2
MW:294.93
EINECS:
Product Categories:
Mol File:82420-34-6.mol
4-Bromo-2-nitrobenzyl bromide Structure
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
MSDS Information
4-Bromo-2-nitrobenzyl bromide Usage And Synthesis
Synthesis
4-Bromo-2-nitrotoluene

60956-26-5

4-BROMO-2-NITROBENZYL BROMIDE

82420-34-6

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
4-Bromo-2-nitrobenzyl bromide Preparation Products And Raw materials
Raw materials4-Bromo-2-nitrotoluene-->4-Bromo-2-nitrobenzyl alcohol-->Methyl 2-methyl-3-nitrobenzoate-->Carbon tetrachloride-->N-Bromosuccinimide-->AIBN
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