Benzonitrile
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| Names | |
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| IUPAC name
Benzonitrile
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| Other names | |
| Identifiers | |
3D model (JSmol)
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| ECHA InfoCard | 100.002.596 |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C7H5N | |
| Molar mass | 103.04 g/mol |
| Density | 1.0 g/ml |
| Melting point | −13 °C |
| Boiling point | 188–91 °C |
| <0.5 g/100 ml (22 °C) | |
Refractive index (nD)
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1.5280 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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
- ^ Cooper, F.C.; Partridge, M. W. (1963). "N-Phenylbenzamidine". Organic Syntheses
{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 4, p. 769. - ^ Pickard, P. L.; Tolbert, T. L. (1973). "Diphenyl Ketimine". Organic Syntheses
{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 5, p. 520. - ^ Gordon K. Anderson, Minren Lin (1990). "Bis(Benzonitrile)Dichloro Complexes of Palladium and Platinum". Inorganic Syntheses. 28: 60–63. doi:10.1002/9780470132593.ch13.
- ^ 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.