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Benzonitrile is a useful solvent and a versatile precursor to many derivatives. It reacts with amines to afford N-substituted benzamides after hydrolysis. [3] It is a precursor to diphenylmethanimine via reaction with phenylmagnesium bromide followed by methanolysis.
Benzophenone imine can also be synthesized by addition of phenylmagnesium bromide to benzonitrile followed by careful hydrolysis (lest the imine be hydrolyzed): [3] C 6 H 5 CN + C 6 H 5 MgBr → (C 6 H 5) 2 C=NMgBr (C 6 H 5) 2 C=NMgBr + H 2 O → (C 6 H 5) 2 C=NH + MgBr(OH) This method is known as Moureu-Mignonac ketimine synthesis. [4]
The structure of a nitrile: the functional group is highlighted blue. In organic chemistry, a nitrile is any organic compound that has a −C≡N functional group.The name of the compound is composed of a base, which includes the carbon of the −C≡N, suffixed with "nitrile", so for example CH 3 CH 2 C≡N is called "propionitrile" (or propanenitrile). [1]
Typically, aryl nitriles are produced by ammoxidation. [2] 3-Chlorobenzonitrile can also be produced by dehydration of the aldoxime of 3-chlorobenzaldehyde. [3]It can also be produced by heating 3-chlorobenzylamine and iodine in ammonium acetate aqueous solution.
Its dehydration yields benzonitrile. It can be hydrolyzed to regenerate benzaldehyde. [5] It reacts with N-chlorosuccinimide in DMF to form benzohydroximoyl chloride, in which chlorine replaces hydrogen on the carbon attached to the nitrogen in benzaldehyde oxime. [6]
Nitriles can also be converted to aldehydes by reduction and hydrolysis. The Stephen aldehyde synthesis uses Tin(II) chloride and hydrochloric acid to yield an aldehyde via the hydrolysis of a resulting iminium salt. Aldehydes can also form using a hydrogen donor followed by in-situ hydrolysis of an imine.
Typical nitrile ligands are acetonitrile, propionitrile, and benzonitrile.The structures of [Ru(NH 3) 5 (NCPh)] n+ have been determined for the 2+ and 3+ oxidation states. Upon oxidation the Ru-NH 3 distances contract and the Ru-NCPh distances elongate, consistent with amines serving as pure-sigma donor ligands and nitriles functioning as pi-acceptors.
Benzoic acid (/ b ɛ n ˈ z oʊ. ɪ k /) is a white (or colorless) solid organic compound with the formula C 6 H 5 COOH, whose structure consists of a benzene ring (C 6 H 6) with a carboxyl (−C(=O)OH) substituent.