Benzonitrile
Benzonitrile is the chemical compound with the formula Template:Chem2, abbreviated PhCN. This aromatic organic compound is a colorless liquid with a cherry or almond like odour. It is mainly used industrially to synthesize the melamine resin precursor benzoguanamine.
Production and reactions
It is prepared by ammoxidation of toluene, that is its reaction with ammonia and oxygen (or air) at Template:Convert.<ref>Template:Cite journal</ref>
In the laboratory it can be prepared by the dehydration of benzamide or benzaldehyde oxime<ref>Template:Cite journal</ref><ref>One Pot Synthesis of Nitriles from Aldehydes and Hydroxylamine Hydrochloride Using Ferrous Sulphate in DMF Under Reflux Condition† Asian Journal of Chemistry; Vol. 24, No. 3 (2012), 1401-1402.</ref> 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.
Applications
Laboratory uses
Benzonitrile is a useful solvent and a versatile precursor to many derivatives. It reacts with amines to afford N-substituted benzamides after hydrolysis.<ref>Template:OrgSynth</ref> It is a precursor to diphenylmethanimine via reaction with phenylmagnesium bromide followed by methanolysis.<ref>Template:OrgSynth</ref>
Benzonitrile forms coordination complexes with transition metals that are both soluble in organic solvents and conveniently labile. One example is [[Bis(benzonitrile)palladium dichloride|Template:Chem2]]. The benzonitrile ligands are readily displaced by stronger ligands, making benzonitrile complexes useful synthetic intermediates.<ref>Template:Cite book</ref>
History
Benzonitrile was reported by Hermann Fehling in 1844. He found the compound as a product from the thermal dehydration of ammonium benzoate. He deduced its structure from the already known analogue reaction of ammonium formate yielding hydrogen cyanide (formonitrile). He also coined the name benzonitrile which gave the name to all the group of nitriles.<ref>Template:Cite journal</ref>
In 2018, benzonitrile was reported to be detected in the interstellar medium.<ref name="SC-20180112">Template:Cite journal</ref>
References
External links
Template:Molecules detected in outer space Template:Authority control