Benzonitrile
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| Benzonitrile | |
|---|---|
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| IUPAC name | Benzonitrile |
| Molar mass | 103.04 g/mol |
| CAS number | [] |
| 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 |
| 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.
Contents |
[edit] As a building block in organic chemistry
PhCN 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]
[edit] As a ligand in coordination chemistry
PhCN forms coordination complexes with late transition metals that are both soluble in organic solvents and conveniently labile. e.g. PdCl2(PhCN)2.[3]
[edit] Safety considerations
Benzonitrile is an eye and skin irritant.
[edit] References
- ^ Cooper F.C.; Partridge, M. W. "N-Phenylbenzamidine" Organic Syntheses, Collected Volume 4, page 769 (1963). http://www.orgsyn.org/orgsyn/pdfs/CV4P0769.pdf
- ^ Pickard, P. L.; Tolbert, T. L. "Diphenyl Ketimine" Organic Syntheses, Collected Volume 5, p.520 (1973). http://www.orgsyn.org/orgsyn/pdfs/CV5P0520.pdf
- ^ Anderson, G. K.; Lin, M. "Bis(benzonitrile)dichloro Complexes of Palladium and Platinum" Inorganic Syntheses, 1990, volume 28, pages 60-63.ISBN 0-471-52619-3
[edit] External links
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