Benzonitrile

This aromatic organic compound is a colorless liquid with a sweet bitter almond odour.

[1] In the laboratory it can be prepared by the dehydration of benzamide or benzaldehyde oxime[2] or by the Rosenmund–von Braun reaction using cuprous cyanide or NaCN/DMSO and bromobenzene.

Hydrogenation of benzonitrile in principle gives benzylamine, but owing to transamination, dibenzylamine and tribenzylamine are also produced.

[4] Benzonitrile forms coordination complexes with transition metals that are both soluble in organic solvents and conveniently labile.

He deduced its structure from the already known analogue reaction of ammonium formate yielding hydrogen cyanide (formonitrile).

Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
NFPA 704 four-colored diamond Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas Flammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuel Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen Special hazards (white): no code