Aniline

File:Aniline-3D-balls.png

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 It is a benzene ring where one of the hydrogen atoms has been replaced by an amine functional group.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

• Aniline-from-xtal-3D-balls.png

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

• Aniline from Nitrobenzene.svg

  Reaction for the production of aniline from nitrobenzene

• 2,6-(iPr)2C6H3NH2sample.jpg

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

• Polyanilines can form upon oxidation of aniline.

• Aniline reaction with bromine .jpg

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

• Anilin delocalization.svg

  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.

• Synthesis of 4,4'-diaminodiphenylmethane.svg

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

• Indigo cake.jpg

  Cake of indigo dye, which is prepared from aniline.