Nitroanilines

The following article is from The Great Soviet Encyclopedia (1979). It might be outdated or ideologically biased.

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.
The Great Soviet Encyclopedia, 3rd Edition (1970-1979). © 2010 The Gale Group, Inc. All rights reserved.
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).