Benzonitrile is the

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

with the formula , abbreviated PhCN. This

aromatic In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to satur ...

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...

is a colorless liquid with a sweet bitter

almond The almond (''Prunus amygdalus'', syn. ''Prunus dulcis'') is a species of tree native to Iran and surrounding countries, including the Levant. The almond is also the name of the edible and widely cultivated seed of this tree. Within the genu ...

odour. It is mainly used as a precursor to the resin benzoguanamine.

Production

It is prepared by

ammoxidation In organic chemistry, ammoxidation is a process for the production of nitriles () using ammonia () and oxygen (). It is sometimes called the SOHIO process, acknowledging that ammoxidation was developed at Standard Oil of Ohio. The usual substrate ...

toluene Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon. It is a colorless, water-insoluble liquid with the smell associated with paint thinners. It is a mono-substituted benzene derivative, consisting of a methyl group (CH3) ...

, that is its reaction with

ammonia Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogenous ...

and oxygen (or air) at . : + 3/2 + → + In the laboratory it can be prepared by the dehydration of

benzamide Benzamide is a organic compound with the chemical formula of C6H5C(O)NH2. It is the simplest amide derivative of benzoic acid. In powdered form, it appears as a white solid, while in crystalline form, it appears as colourless crystals. It is slig ...

or by the

Rosenmund–von Braun reaction The Rosenmund–von Braun synthesis is an organic reaction in which an aryl halide reacts with cuprous cyanide to yield an aryl nitrile. : The reaction was named after Karl Wilhelm Rosenmund who together with his Ph.D. student Erich Struck disc ...

using cuprous cyanide or NaCN/ DMSO and bromobenzene. :

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 diphenylketimine (b.p. 151 °C, 8 mm Hg) via reaction with

phenylmagnesium bromide Phenylmagnesium bromide, with the simplified formula , is a magnesium-containing organometallic compound. It is commercially available as a solution in diethyl ether or tetrahydrofuran (THF). Phenylmagnesium bromide is a Grignard reagent. It is ...

followed by methanolysis. Benzonitrile forms

coordination complex A coordination complex consists of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of bound molecules or ions, that are in turn known as '' ligands'' or complexing agents. M ...

es 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.

History

Benzonitrile was reported by

Hermann Fehling Hermann or Herrmann may refer to: * Hermann (name), list of people with this name * Arminius, chieftain of the Germanic Cherusci tribe in the 1st century, known as Hermann in the German language * Éditions Hermann, French publisher * Hermann, M ...

in 1844. He found the compound as a product from the thermal dehydration of

ammonium benzoate Ammonium benzoate, a white powder-like substance, is the ammonium salt of benzoic acid. This compound is prepared by the reaction of benzoic acid and ammonia Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A s ...

. He deduced its structure from the already known analogue reaction of ammonium formate yielding

hydrogen cyanide Hydrogen cyanide, sometimes called prussic acid, is a chemical compound with the formula HCN and structure . It is a colorless, extremely poisonous, and flammable liquid that boils slightly above room temperature, at . HCN is produced on a ...

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

nitrile In organic chemistry, a nitrile is any organic compound that has a functional group. The prefix '' cyano-'' is used interchangeably with the term ''nitrile'' in industrial literature. Nitriles are found in many useful compounds, including me ...

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

interstellar medium In astronomy, the interstellar medium is the matter and radiation that exist in the space between the star systems in a galaxy. This matter includes gas in ionic, atomic, and molecular form, as well as dust and cosmic rays. It fills interstella ...

References

External links

* {{Authority control Aromatic solvents Phenyl compounds Benzonitriles