Benzonitrile
Encyclopedia
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
, or by the reaction of sodium cyanide
with bromobenzene.
followed by methanolysis.
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.
until it decomposed, and one of the products was benzonitrile. He was able to determine the structure of the product from the already known analogue reaction of ammonium formate
yielding hydrocyanic acid. He also coined the name benzonitrile which gave the name to all the group of nitrile
s.
Chemical compound
A chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...
with the formula C6H5CN, abbreviated PhCN. This aromatic organic compound
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
is colourless, with a sweet almond odour. It is prepared by the dehydration of benzamide
Benzamide
Benzamide is an off-white solid with the chemical formula of C6H5CONH2. It is a derivative of benzoic acid. It is slightly soluble in water, and soluble in many organic solvents.- External links :* *...
, or by the reaction of sodium cyanide
Sodium cyanide
Sodium cyanide is an inorganic compound with the formula NaCN. This highly toxic colorless salt is used mainly in gold mining but has other niche applications...
with bromobenzene.
Applications
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 bromidePhenylmagnesium bromide
Phenylmagnesium bromide, with the simplified formula , is a magnesium-containing organometallic compound. It is so commonly used that it is commercially available as a solution in diethyl ether or tetrahydrofuran . Phenylmagnesium bromide is a Grignard reagent...
followed by methanolysis.
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.
History
Benzonitrile was discovered by Hermann Fehling in 1844. He heated ammonium benzoateAmmonium benzoate
Ammonium benzoate, a white solid, is the ammonium salt of benzoic acid.It is a white metal substance that is highly reactive with Sodium Phosphate....
until it decomposed, and one of the products was benzonitrile. He was able to determine the structure of the product from the already known analogue reaction of ammonium formate
Ammonium formate
Ammonium formate, NH4HCO2, is the ammonium salt of formic acid. It is a colorless, hygroscopic, crystalline solid.-Uses:Pure ammonium formate decomposes into formamide and water when heated, and this is its primary use in industry...
yielding hydrocyanic acid. He also coined the name benzonitrile which gave the name to all the group of nitrile
Nitrile
A nitrile is any organic compound that has a -C≡N functional group. The prefix cyano- is used interchangeably with the term nitrile in industrial literature. Nitriles are found in many useful compounds, one example being super glue .Inorganic compounds containing the -C≡N group are not called...
s.