Benzonitrile

Benzonitrile is the chemical compound with the formula C6H5CN, abbreviated PhCN. This aromatic organic compound is colourless, with a sweet almond odour. It is prepared by the dehydration of benzamide and the reaction of sodium cyanide with bromobenzene.

As a building block in organic chemistry
PhCN is a useful solvent and a versatile precursor to many derivatives. It reacts with amines to afford N-substituted benzamides after hydrolysis, It is a precursor to Ph2C=NH  (b.p. 151 °C, 8 mm Hg) via reaction with phenylmagnesium bromide followed by hydrolysis.

As a ligand in coordination chemistry
PhCN forms coordination complexes with late transition metals that are both soluble in organic solvents and conveniently labile. e.g. PdCl2(PhCN)2.

Safety considerations
Benzonitrile is an eye and skin irritant.