Benzonitrile
From Wikipedia, the free encyclopedia
| Benzonitrile | |
|---|---|
 |
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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 | 1/C7H5N/c8-6- 7-4-2-1-3-5-7/h1-5H |
| Hazards | |
| EU classification | Harmful (Xn) |
| EU Index | 608-012-00-3 |
| NFPA 704 |
 2
3
0
|
| R-phrases | R21/22 |
| S-phrases | (S2), S23 |
| Flash point | 75 °C |
| Autoignition temperature |
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 |
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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 and the reaction of sodium cyanide with bromobenzene.
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[edit] 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 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]
[edit] History
Benzonitrile was discovered by Hermann Fehling in 1844. He heated ammonium benzoate till 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 formiate yielding hydrocyanic acid. He also coined the name benzonitrile which gave the name to all the group of nitriles.[4]
[edit] References
- ^ Cooper, F.C.; Partridge, M. W. (1963). "N-Phenylbenzamidine". Org. Synth.; Coll. Vol. 4: 769.
- ^ Pickard, P. L.; Tolbert, T. L. (1973). "Diphenyl Ketimine". Org. Synth.; Coll. Vol. 5: 520.
- ^ Gordon K. Anderson, Minren Lin (1990). "Bis(Benzonitrile)Dichloro Complexes of Palladium and Platinum". Inorganic Syntheses 28: 60-63. doi:.
- ^ Hermann Fehling (1844). "Ueber die Zersetzung des benzoësauren Ammoniaks durch die Wärme". Annalen der Chemie und Pharmacie 49 (1): 91 - 97. doi:.
