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IUPAC name Benzonitrile
Molar mass 103.04 g/mol
CAS number 100-47-0
Density 1.0 g/ml
Solubility <0.5 g/100 ml (22 °C)
Melting point

−13 °C

Boiling point

188–91 °C

SMILES N#Cc1ccccc1
InChI InChI=1/C7H5N/c8-6-
EU classification Harmful (Xn)
EU Index 608-012-00-3
NFPA 704
R-phrases R21/22
S-phrases (S2), S23
Flash point 75 °C
550 °C
Explosive limits 1.4–7.2%
RTECS number DI2450000
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

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 and the reaction of sodium cyanide with bromobenzene.


Benzonitrile is a useful solvent and a versatile precursor to many derivatives. It reacts with amines to afford N-substituted benzamides after hydrolysis,[1] It is a precursor to Ph2C=NH (b.p. 151 °C, 8 mm Hg) via reaction with phenylmagnesium bromide followed by hydrolysis.[2]

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.[3]


  1. ^ Cooper, F.C.; Partridge, M. W. (1963). "N-Phenylbenzamidine". Org. Synth.; Coll. Vol. 4: 769. 
  2. ^ Pickard, P. L.; Tolbert, T. L. (1973). "Diphenyl Ketimine". Org. Synth.; Coll. Vol. 5: 520. 
  3. ^ Gordon K. Anderson, Minren Lin. "Bis(Benzonitrile)Dichloro Complexes of Palladium and Platinum". Inorganic Syntheses 28: 60-63. doi:10.1002/9780470132593.ch13.
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Benzonitrile". A list of authors is available in Wikipedia.
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