Benzonitrile

Benzonitrile

Skeletal formula Ball-and-stick model
Names
IUPAC name Benzonitrile
Other names cyanobenzene phenyl cyanide
Identifiers
CAS Number	100-47-0 Y
ChEBI	CHEBI:27991 Y
ChEMBL	ChEMBL15819 Y
ChemSpider	7224 Y
Jmol 3D model	Interactive image
KEGG	C09814 Y
PubChem	7505
RTECS number	DI2450000
UNII	9V9APP5H5S Y
InChI InChI=1S/C7H5N/c8-6-7-4-2-1-3-5-7/h1-5H Y Key: JFDZBHWFFUWGJE-UHFFFAOYSA-N Y InChI=1/C7H5N/c8-6-7-4-2-1-3-5-7/h1-5H Key: JFDZBHWFFUWGJE-UHFFFAOYAY
SMILES c1ccc(cc1)C#N
Properties
Chemical formula	C7H5N
Molar mass	103.12 g/mol
Density	1.0 g/ml
Melting point	−13 °C (9 °F; 260 K)
Boiling point	188 to 191 °C (370 to 376 °F; 461 to 464 K)
Solubility in water	<0.5 g/100 ml (22 °C)
Refractive index (nD)	1.5280
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Benzonitrile is the chemical compound with the formula C₆H₅CN, abbreviated PhCN. This aromatic organic compound is a colorless liquid with a sweet almond odour. It is mainly used as a precursor to the resin benzoguanamine.

Production

It is prepared by ammoxidation of toluene, that is its reaction ammonia and oxygen (or air) at 400 to 450 °C.

C₆H₅CH₃ + 3/2 O₂ + NH₃ → C₆H₅CN + 3 H₂O

In laboratory it can be prepared by the dehydration of benzamide or by the Rosenmund-von Braun reaction 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 Ph₂C=NH (b.p. 151 °C, 8 mm Hg) via reaction with phenylmagnesium bromide followed by methanolysis.

Benzonitrile forms coordination complexes with transition metals that are both soluble in organic solvents and conveniently labile. One example is PdCl₂(PhCN)₂. The benzonitrile ligands are readily displaced by stronger ligands, making benzonitrile complexes useful synthetic intermediates.

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

External links

• International Chemical Safety Card 1103