Aniline

Ball-and-stick model of aniline. The black balls are carbon, the white balls are hydrogen, and the blue ball is nitrogen. The dotted line shows the benzene ring.

Aniline is an organic compound with the formula C
6H
5NH
2. It is a benzene ring where one of the hydrogen atoms has been replaced by an amine functional group. Because of this, it is also called aminobenzene.

Production

In the chemical industry, aniline is produced by the hydrogenation of nitrobenzene.

Aniline Media

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  Ball-and-stick model of aniline from the crystal structure at 252 K

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  Reaction for the production of aniline from nitrobenzene

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  Sample of 2,6-diisopropylaniline, a colorless liquid when pure, illustrating the tendency of anilines to air-oxidize to dark-colored products.

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  Polyanilines can form upon oxidation of aniline.

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  Aniline can react with bromine even in room temperatures in water. Acetyl chloride is added to prevent tribromination.

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  The lone electron pair on the nitrogen delocalizes into the pi system of the benzene ring. This is responsible for nitrogen's weaker basicity compared to other amines.

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  Most aniline is consumed in the production of methylenedianiline, a precursor to polyurethanes.

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  Cake of indigo dye, which is prepared from aniline.