Nicotinonitrile or 3-cyanopyridine is an organic compound with the formula NCC<sub>5</sub>H<sub>4</sub>N. The molecule consists of a pyridine ring with a nitrile group attached to the 3-position. A colorless solid, it is produced by ammoxidation of 3-methylpyridine:
Nicotinonitrile is a precursor to the vitamin niacin.
Nitrilase-catalyzed hydrolysis of 3-cyanopyridine by means of immobilized Rhodococcus rhodochrous J1 strains leads in quantitative yield to nicotinamide (vitamin B<sub>3</sub>). The enzyme allows for a more selective synthesis as further hydrolysis of the amide to nicotinic acid is avoided.
Oxidation of 3-cyanopyridine with hydrogen peroxide gives 3-cyanopyridine-N-oxide, which hydrolyzes to nicotinic acid N-oxide, a precursor to pharmaceuticals.