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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.
Benzonitrile 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.
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.
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Benzonitrile". A list of authors is available in Wikipedia.|