5-Bromo-3-nitro-benzene-1,2-diamine

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5-Bromo-3-nitro-benzene-1,2-diamine Basic information
Product Name:5-Bromo-3-nitro-benzene-1,2-diamine
Synonyms:5-Bromo-3-nitro-benzene-1,2-diamine;4-Bromo-6-nitro-1,2-phenylenediamine;1,2-Benzenediamine, 5-bromo-3-nitro-
CAS:84752-20-5
MF:C6H6BrN3O2
MW:232.03
EINECS:
Product Categories:Aromatic Building Blocks
Mol File:84752-20-5.mol
5-Bromo-3-nitro-benzene-1,2-diamine Structure
5-Bromo-3-nitro-benzene-1,2-diamine Chemical Properties
storage temp. under inert gas (nitrogen or Argon) at 2–8 °C
AppearanceBrown to reddish brown Solid
Safety Information
MSDS Information
5-Bromo-3-nitro-benzene-1,2-diamine Usage And Synthesis
Synthesis
4-BroMo-2,6-dinitroaniline

62554-90-9

5-Bromo-3-nitro-benzene-1,2-diamine

84752-20-5

General procedure for the synthesis of 3-nitro-5-bromobenzene-1,2-diamine from 2,6-dinitro-4-bromoaniline: a mixture of 4-bromo-2,6-dinitroaniline (5.5 g, 21.2 mmol) and ammonium sulfide (10.5 mL, 21.2 mmol) in ethanol (150 mL) was heated and reacted for 1 hr at 90 °C. Thin layer chromatography (TLC) monitoring showed incomplete consumption of the feedstock. Ammonium sulfide (10.5 mL, 21.2 mmol) was added and the reaction was continued with stirring at 90 °C for 1 hour. Upon completion of the reaction, the mixture was concentrated and purified by silica gel column chromatography (eluent: petroleum ether/dichloromethane = 1:1) to afford the target compound 3-nitro-5-bromobenzene-1,2-diamine (2.5 g, 51% yield) as a red solid. Liquid chromatography-mass spectrometry (LCMS) analysis results: m/z 230, 232 ([M+H]+).

References[1] Patent: WO2016/168682, 2016, A2. Location in patent: Paragraph 0288
[2] Patent: US2012/88767, 2012, A1. Location in patent: Page/Page column 13; 15; 19
[3] Analytical Chemistry, 1983, vol. 55, # 6, p. 963 - 965
5-Bromo-3-nitro-benzene-1,2-diamine Preparation Products And Raw materials
Raw materials4-BroMo-2,6-dinitroaniline-->Ethanol-->Ammonium sulfide
Preparation Products6-Bromo-2-methyl-4-nitro-1H-benzo[d]imidazole
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