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| Names | |||
|---|---|---|---|
| Preferred IUPAC name Benzonitrile | |||
| Systematic IUPAC name Benzenecarbonitrile | |||
| Other names | |||
| Identifiers | |||
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3D model (JSmol) | |||
| 506893 | |||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider |
| ||
| ECHA InfoCard | 100.002.596 | ||
| EC Number |
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| 2653 | |||
| KEGG |
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| RTECS number |
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| UNII | |||
| UN number | 2224 | ||
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| Properties | |||
| C6H5(CN) | |||
| Molar mass | 103.12 g/mol | ||
| Density | 1.0 g/ml | ||
| Melting point | −13 °C (9 °F; 260 K) | ||
| Boiling point | 188 to 191 °C (370 to 376 °F; 461 to 464 K) | ||
| <0.5 g/100 ml (22 °C) | |||
| −65.19·10−6 cm3/mol | |||
Refractive index (nD) | 1.5280 | ||
| Hazards | |||
| GHS labelling: | |||
 | |||
| Warning | |||
| H302,H312 | |||
| P264,P270,P280,P301+P312,P302+P352,P312,P322,P330,P363,P501 | |||
| NFPA 704 (fire diamond) | |||
| Flash point | 75 °C (167 °F; 348 K) | ||
| 550 °C (1,022 °F; 823 K) | |||
| Explosive limits | 1.4–7.2% | ||
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
Benzonitrile is thechemical compound with the formulaC6H5(CN), abbreviatedPhCN. Thisaromaticorganic compound is a colorless liquid with a sweet bitteralmond odour. It is mainly used as a precursor to the resinbenzoguanamine.
It is prepared byammoxidation oftoluene, that is its reaction withammonia and oxygen (or air) at 400 to 450 °C (752 to 842 °F).[1]
In the laboratory it can be prepared by the dehydration ofbenzamide orbenzaldehyde oxime[2] or by theRosenmund–von Braun reaction usingcuprous cyanide orNaCN/DMSO andbromobenzene.
Hydrogenation of benzonitrile in principle givesbenzylamine, but owing to transamination,dibenzylamine andtribenzylamine are also produced.
Benzonitrile is a useful solvent and a versatile precursor to many derivatives. It reacts with amines to afford N-substituted benzamides after hydrolysis.[3] It is a precursor to diphenylmethanimine via reaction withphenylmagnesium bromide followed bymethanolysis.[4]
Benzonitrile formscoordination complexes with transition metals that are both soluble in organic solvents and conveniently labile. One example isPdCl2(PhCN)2. The benzonitrile ligands are readily displaced by stronger ligands, making benzonitrile complexes useful synthetic intermediates.[5]
Benzonitrile was reported byHermann Fehling in 1844. He found the compound as a product from the thermal dehydration ofammonium benzoate. He deduced its structure from the already known analogue reaction ofammonium formate yieldinghydrogen cyanide (formonitrile). He also coined the name benzonitrile which gave the name to all the group ofnitriles.[6]
In 2018, benzonitrile was reported to be detected in theinterstellar medium.[7]
| Authority control databases: National |
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