2-AMINO-3-CHLORO-5-NITROBENZOTRIFLUORIDE Chemical Properties

Melting point:

115-116 °C(Solv: acetic acid (64-19-7))

Boiling point:

286.0±35.0 °C(Predicted)

Density 

1.614±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

-3.90±0.46(Predicted)

CAS DataBase Reference

400-67-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36/37/39

Hazard Note 

Irritant

HS Code 

2921490090

2-AMINO-3-CHLORO-5-NITROBENZOTRIFLUORIDE Usage And Synthesis

Uses

2-Amino-3-chloro-5-nitrobenzotrifluoride is a useful intermediate for the preparation of monoazo dyes.

Synthesis

General procedure for the synthesis of 2-chloro-4-nitro-6-(trifluoromethyl)aniline from 2-amino-5-nitrobenzotrifluoride: 4-nitro-2-(trifluoromethyl)aniline (15 g) and N-chlorosuccinimide (10.7 g) were dissolved in acetonitrile (100 ml) in a sealed microwaveable reaction flask and heated to 150°C for 15 minutes. After completion of the reaction, the mixture was cooled to room temperature and poured into a mixture of 5% sodium hydroxide solution (500 ml) and ethyl acetate (400 ml). The organic phase was separated, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Purification by fast column chromatography afforded 17.0 g (97% yield) of 2-chloro-4-nitro-6-(trifluoromethyl)aniline as a yellow solid.LC-MS (m/z) 240 (MH+); tR=4.76, (UV, ELSD) purity 97% and 96%, respectively.1H NMR (500 MHz, DMSO-d6) δ: 7.15 (s , 2H), 8.15 (d, 1H), 8.40 (d, 1H).

References

[1] Patent: WO2006/29623, 2006, A1. Location in patent: Page/Page column 60-61
[2] Patent: WO2005/87754, 2005, A1. Location in patent: Page/Page column 46
[3] Industrial and Engineering Chemistry, 1953, vol. 45, p. 1730,1732
[4] Industrial and Engineering Chemistry, 1954, vol. 46, p. 2213,2218, 2219

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