Nitro-aniline anilines

Only the mono-amines are described here. The diamines are more frequently encountered as reduction products of dinitrobenzenes and nitro-anilines, and the chief reactions of the phenylenediamines are therefore given in Section 23, pp. 384-388. 

Various basic substances, such as aromatic amines (naphthyl-amines dissolve with difficulty in dil. HCl, diphenylamine only in cone. HCl, triphenylamine insoluble) nitro-anilines some amino-carboxylic acids. 

Its production was 621 t and the average price 0.75/kg in 1987. Direct YeUow 44 (64) is prepared by phosgenation of an equimolar mixture of metanilic acid coupled to o-anisidinomethanesulfonic acid (with subsequent hydrolysis of the methanesulfonic acid group) and nitro aniline coupled to sahcychc acid (with subsequent reduction of the nitro group). 

T -nitro aniline (PNA) [100-01-6] ammonia T -phenylenedi-amine gasoline antioxidants, dyes, mbber chemicals... 

Nitrophenylarsonic acid has been prepared by heating p-nitrobenzenediazonium chloride with arsenious acid in hydrochloric acid, by the action of -nitrobenzenediazonium chloride on sodium arsenite, by the action of sodium arsenite on sodium -nitrobenzeneisodiazo oxide, by the diazotization of -nitro-aniline in acetic acid in the presence of arsenic chloride and cuprous chloride, and by the reaction of -nitrobenzenediazonium borofluoride with sodium arsenite in the presence of cuprous chloride. ... 

Methoxy-anilin 4-MethyI-anilin 4-Brom-anilin 3-Nitro-anilin I-Naphthylamin... 

N-Formyl-2-nitro-anilin wird in acetatgepuffertem wabrigem Athanol zu Benzimida-zol-3-oxid reduziert3 ... 

N-Alkyl-2-nitro-aniline mit a-standigem Wasserstoff lassen sich in saurem Milieu mit guten Ausbeuten zu Benzimidazolen cyclisieren6 ... 

Bei der Reduktion von 4-Nitro-l-phenylthioazo-benzol wird 4-Nitro-anilin (bei -0,6 V) bzw. /,4-Diamino-benzol (bei —1,2 V) erhalten5 ... 

A group with a more powerful (electron-withdrawing) inductive effect, e.g. NOa, is found to have rather more influence. Electron-withdrawal is intensified when the nitro group is in the o- or p-position, for the interaction of the unshared pair of the amino nitrogen with the delocalised it orbital system of the benzene nucleus is then enhanced. The neutral molecule is thus stabilised even further with respect to the cation, resulting in further weakening as a base. Thus the nitro-anilines are found to have related p a values ... 

---