Benzonitrile

Benzonitrile
IUPAC name Benzonitrile
Other names cyanobenzene phenyl cyanide
Identifiers
CAS number	100-47-0 Y
PubChem	7505
ChemSpider	7224 Y
UNII	9V9APP5H5S Y
KEGG	C09814 Y
ChEBI	CHEBI:27991 Y
ChEMBL	CHEMBL15819 Y
Jmol-3D images	Image 1
SMILES c1ccc(cc1)C#N
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
Properties
Molecular formula	C7H5N
Molar mass	103.04 g/mol
Density	1.0 g/ml
Melting point	−13 °C
Boiling point	188–191 °C
Solubility in water	<0.5 g/100 ml (22 °C)
Refractive index (nD)	1.5280
Hazards
EU Index	608-012-00-3
EU classification	Harmful (Xn)
R-phrases	R21/22
S-phrases	(S2), S23
NFPA 704	2 3 0
Flash point	75 °C
Autoignition temperature	550 °C
Explosive limits	1.4–7.2%
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox 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, or by the reaction of sodium cyanide 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,^[1] It is a precursor to Ph₂C=NH (b.p. 151 °C, 8 mm Hg) via reaction with phenylmagnesium bromide followed by methanolysis.^[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]

History

Benzonitrile was discovered by Hermann Fehling in 1844. He heated ammonium benzoate 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 nitriles.^[4]

References

1. ^ Cooper, F.C.; Partridge, M. W. (1963), "N-Phenylbenzamidine", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv4p0769 ; Coll. Vol. 4: 769 
2. ^ Pickard, P. L.; Tolbert, T. L. (1973), "Diphenyl Ketimine", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv5p0520 ; Coll. Vol. 5: 520 
3. ^ Gordon K. Anderson, Minren Lin (1990). "Bis(Benzonitrile)Dichloro Complexes of Palladium and Platinum". Inorganic Syntheses. Inorganic Syntheses 28: 60–63. doi:10.1002/9780470132593.ch13. ISBN 9780470132593. 
4. ^ Hermann Fehling (1844). "Ueber die Zersetzung des benzoësauren Ammoniaks durch die Wärme". Annalen der Chemie und Pharmacie 49 (1): 91–97. doi:10.1002/jlac.18440490106. 

External links

• International Chemical Safety Card 1103