Nicotinonitrile

Precautionary statementsP261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Nicotinonitrile or 3-cyanopyridine is an organic compound with the formula NCC5H4N. 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:

H3CC5H4N + NH3 + 1.5 O2 → NCC5H4N + 3 H2O

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 B3). 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.