Aniline  is an  organic compound  with the  formula  C 6 H 5 NH 2 . Consisting of a  phenyl group attached to an  amino group , aniline is the prototypical aromatic amine. Its main use is in the manufacture of precursors to  polyurethane  and other industrial chemicals. Like most volatile amines, it possesses the odour of rotten fish. It ignites readily, burning with a smoky flame characteristic of aromatic compounds.  Aniline is a planar molecule. The amine is nearly planar owing to conjugation of the lone pair with the aryl substituent. The C-N distance is correspondingly shorter. In aniline, the C-N and C-C distances are close to 1.39 Å, indicating the  π -bonding between N and C.   Industrial aniline production involves two steps. First,  benzene  is  nitrated  with a concentrated mixture of  nitric acid  and  sulfuric acid  at 50 to 60 °C to yield  nitrobenzene . The nitrobenzene is ...