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2-Bromo-4-chloro-6-nitrophenylamine

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2-Bromo-4-chloro-6-nitrophenylamine Basic information
Product Name:2-Bromo-4-chloro-6-nitrophenylamine
Synonyms:2-Bromo-4-chloro-6-nitrobenzenamine;2-Amino-3-bromo-5-chloronitrobenzene;Benzenamine, 2-bromo-4-chloro-6-nitro-;2-BROMO-4-CHLORO-6-NITROPHENYLAMINE ISO 9001:2015 REACH;2-Bromo-4-chloro-6-nitroaniline, 97%;2-BROMO-4-CHLORO-6-NITROANILINE;2-Bromo-4-chloro-6-nitrophenylamine
CAS:827-25-8
MF:C6H4BrClN2O2
MW:251.47
EINECS:
Product Categories:Alkylanilines;Anilines, Amides & Amines;Bromine Compounds;Chlorine Compounds;Nitro Compounds
Mol File:827-25-8.mol
2-Bromo-4-chloro-6-nitrophenylamine Structure
2-Bromo-4-chloro-6-nitrophenylamine Chemical Properties
Melting point 106 °C
Boiling point 329.3±37.0 °C(Predicted)
density 1.909±0.06 g/cm3(Predicted)
storage temp. 2-8°C(protect from light)
pka-3.20±0.25(Predicted)
AppearanceWhite to yellow Solid
CAS DataBase Reference827-25-8(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
HS Code 2921420090
MSDS Information
2-Bromo-4-chloro-6-nitrophenylamine Usage And Synthesis
Synthesis Reference(s)Tetrahedron Letters, 35, p. 7055, 1994 DOI: 10.1016/0040-4039(94)88224-X
Synthesis
4-Chloro-2-nitroaniline

89-63-4

2-BROMO-4-CHLORO-6-NITROPHENYLAMINE

827-25-8

General procedure for the synthesis of 2-nitro-4-chloro-6-bromoaniline from 4-chloro-2-nitroaniline: 4-chloro-2-nitroaniline (5.1 g, 30 mmol) and N-bromosuccinimide (6.2 g, 36 mmol) were dissolved in acetonitrile (50 mL) and the reaction was heated to reflux overnight. After completion of the reaction, the mixture was cooled to room temperature and diluted with ethyl acetate (50 mL). Subsequently, the mixture was washed with saturated aqueous potassium carbonate (100 mL x 2). The organic phase was separated, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the target compound 2-nitro-4-chloro-6-bromoaniline (109a) as a yellow solid (8.1 g, 100% yield).LCMS analysis showed [M + H]+ of 253.1 H NMR (500 MHz, CDCl3) δ 8.17 (d, J = 2.5 Hz, 1H), 1 H 7.71 (d, J = 2.5 Hz, 1H), 6.64 (s, 2H).

References[1] Patent: US2013/116262, 2013, A1. Location in patent: Paragraph 0260
[2] Patent: WO2018/13776, 2018, A1. Location in patent: Page/Page column 108
[3] Patent: WO2018/13770, 2018, A1. Location in patent: Page/Page column 80
[4] Patent: WO2018/13774, 2018, A1. Location in patent: Page/Page column 155
[5] Tetrahedron Letters, 1994, vol. 35, # 38, p. 7055 - 7056
2-Bromo-4-chloro-6-nitrophenylamine Preparation Products And Raw materials
Raw materials4-Chloro-2-nitroaniline-->N-Bromosuccinimide-->Acetonitrile
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