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)

Appearance

White to yellow Solid

CAS DataBase Reference

827-25-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

HS Code 

2921420090

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

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

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