Nitroanilines

Nitroanilines

 

products of the replacement of hydrogen atoms in the aniline ring, C6H5NH2, by nitro groups, —NO2. They may contain one to five nitro groups.

The meta-, ortho-, and para- isomers of mononitroanilines have industrial significance. They are yellow crystalline compounds that melt at 114.0°, 71.0°, and 147.0°C, respectively, and are poorly soluble in water but readily soluble in organic solvents. The ortho- and para- isomers are weak bases and are less soluble in acids than the meta- isomer, which is a stronger base. Upon heating with aqueous alkaline solutions, the NH2 groups in o-nitroaniline and p-nitroaniline are replaced by OH groups with the formation of nitrophenols.

Nitroanilines with more than one nitro group are explosive. In industry, o-nitroaniline and p-nitroaniline are obtained by heating the corresponding nitrochlorobenzenes with ammonia; m-nitroaniline is produced by partial reduction of m-dinitroben-zene with sodium sulfide. Nitroanilines are blood poisons, and the combined action of nitroanilines and ethyl alcohol is particularly dangerous. Nitroanilines are intermediates in the production of azo dyes and a number of drugs.

REFERENCE

Vorontsov, I. I. Poluprodukty anilinokrasochnoi promyshlennosti. Moscow, 1955.
References in periodicals archive ?
Dawis-Ward, A mild, one-pot synthesis of disubstituted benzimidazoles from 2- nitroanilines, Tet.
Later on, the synthesis of benzimidazole from N-substituted 2- nitroaniline on hydrogenation by using palladium catalyst was also reported [10].
Several coumarins and variants of nitro aromatic systems, such as nitrocoumarins, nitroanilines, and nitroindolines, were synthesized and studied for their photoreactivity (Table 1).
Fluazinam is a nitroanilines fungicide with excellent control effect on such bacteria as Alternaria, Botrytis, Phytophthora, Plasmopara, Sclerotinia, etc.