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.
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.
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.
[1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 11, p. 2589 - 2593
