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.

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Applications

Benzonitrile is a useful solvent and a versatile precursor to many derivatives. It reacts with amines to afford N-substituted benzamides after hydrolysis,^[1] It is a precursor to Ph₂C=NH (b.p. 151 °C, 8 mm Hg) via reaction with phenylmagnesium bromide followed by hydrolysis.^[2]

Benzonitrile can form coordination complexes with late transition metals that are both soluble in organic solvents and conveniently labile, e.g. PdCl₂(PhCN)₂. The benzonitrile ligands are readily displaced by stronger ligands, making benzonitrile complexes useful synthetic intermediates.^[3]

References

1. ^ Cooper, F.C.; Partridge, M. W. (1963). "N-Phenylbenzamidine". Org. Synth.; Coll. Vol. 4: 769. 
2. ^ Pickard, P. L.; Tolbert, T. L. (1973). "Diphenyl Ketimine". Org. Synth.; Coll. Vol. 5: 520. 
3. ^ Gordon K. Anderson, Minren Lin. "Bis(Benzonitrile)Dichloro Complexes of Palladium and Platinum". Inorganic Syntheses 28: 60-63. doi:10.1002/9780470132593.ch13.