Benzonitrile is the chemical compound with the formula C6H5(CN), abbreviated PhCN. This aromatic organic compound is a colorless liquid with a cherry or almond like odour. It is mainly used industrially to synthesize the melamine resin precursor benzoguanamine.
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| Names | |||
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| Preferred IUPAC name Benzonitrile | |||
| Systematic IUPAC name Benzenecarbonitrile | |||
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| Identifiers | |||
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3D model (JSmol) |
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| 506893 | |||
| ChEBI |
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| ChEMBL |
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| ChemSpider |
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| ECHA InfoCard | 100.002.596 | ||
| EC Number |
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| 2653 | |||
| KEGG |
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PubChem CID |
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| RTECS number |
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| UNII |
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| UN number | 2224 | ||
CompTox Dashboard (EPA) |
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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: | |||
Signal word | Warning | ||
| H302, H312 | |||
| P264, P270, P280, P301+P312, P302+P352, P312, P322, P330, P363, P501 | |||
| NFPA 704 (fire diamond) | 3 2 0 | ||
| 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 their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references | |||
Production and reactions
It is prepared by ammoxidation of toluene, that is its reaction with ammonia and oxygen (or air) at 400 to 450 °C (752 to 842 °F).
- C6H5CH3 + 3/2 O2 + NH3 → C6H5(CN) + 3 H2O
In the laboratory it can be prepared by the dehydration of benzamide or benzaldehyde oxime or by the Rosenmund–von Braun reaction using cuprous cyanide or NaCN/DMSO and bromobenzene.
Hydrogenation of benzonitrile in principle gives benzylamine, but owing to transamination, dibenzylamine and tribenzylamine are also produced.
Applications
Laboratory uses
Benzonitrile is a useful solvent and a versatile precursor to many derivatives. It reacts with amines to afford N-substituted benzamides after hydrolysis. It is a precursor to diphenylmethanimine via reaction with phenylmagnesium bromide followed by methanolysis.
Benzonitrile forms coordination complexes with transition metals that are both soluble in organic solvents and conveniently labile. One example is PdCl2(PhCN)2. The benzonitrile ligands are readily displaced by stronger ligands, making benzonitrile complexes useful synthetic intermediates.
History
Benzonitrile was reported by Hermann Fehling in 1844. He found the compound as a product from the thermal dehydration of ammonium benzoate. He deduced its structure from the already known analogue reaction of ammonium formate yielding hydrogen cyanide (formonitrile). He also coined the name benzonitrile which gave the name to all the group of nitriles.
In 2018, benzonitrile was reported to be detected in the interstellar medium.
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