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Benzonitrile is the chemical compound with the formula , abbreviated . This is a colorless liquid with a or like odour. It is mainly used industrially to synthesize the precursor .


Production and reactions
It is prepared by of , that is its reaction with and oxygen (or air) at .
(2000). 9783527306732
+ 3/2 + → +
In the laboratory it can be prepared by the dehydration of or benzaldehyde oxime or by the Rosenmund–von Braun reaction using or /DMSO and .

of benzonitrile in principle gives , but owing to transamination, and 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. It is a precursor to diphenylmethanimine via reaction with phenylmagnesium bromide followed by .

Benzonitrile forms coordination complexes with transition metals that are both soluble in organic solvents and conveniently labile. One example is . The benzonitrile ligands are readily displaced by stronger ligands, making benzonitrile complexes useful synthetic intermediates.

(1990). 9780470132593, John Wiley & Sons.


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 yielding (formonitrile). He also coined the name benzonitrile which gave the name to all the group of .

In 2018, benzonitrile was reported to be detected in the interstellar medium.


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