Chemical Properties
yellow to brownish powder. 2-Amino-5-nitrobenzonitrile [17420-30-3], 2-cyano-4-nitroaniline, Mr 163.13, mp 210℃, is readily soluble in acetone, chloroform, and benzene; it is sparingly soluble in water and ethanol. As already mentioned, the reaction of 2-chloro5-nitrobenzonitrile with ammonia gives 2-amino-5-nitrobenzonitrile, an intermediate for azo dyes.
Uses
5-Nitroanthranilonitrile is mainly used in the synthesis of disperse dyes and is an important intermediate for disperse dyes. It is used to synthesize various high-temperature or medium-temperature disperse dyes such as Disperse Ruby SE-GFL, Disperse Scarlet S-FL, Disperse Blue SE-2R, and Disperse Violet SR.
Production Methods
A newer synthetic route
starts from 6-nitroisatoic anhydride [2H-3,1-benzoxazine-6-nitro-2,4 (1H)-dione]: the latter is
converted into 2-amino-5-nitrobenzonitrile by
reaction with ammonia, subsequent treatment
with phosgene in dimethylformamide or Nmethylpyrrolidone, followed by hydrolysis of
the formamidine.
Synthesis Reference(s)
Journal of the American Chemical Society, 82, p. 3152, 1960
DOI: 10.1021/ja01497a043
References
[1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 11, p. 2589 - 2593
