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 then hydrogenated (typically at 200–300 °C) in the presence of metal catalysts . The reduction