Benzonitrile
| Names | |
|---|---|
| IUPAC name
Benzonitrile
| |
| Preferred IUPAC name
Benzonitrile | |
| Systematic IUPAC name
Benzenecarbonitrile | |
| Other names
Cyanobenzene
Phenyl cyanide | |
| Properties | |
| C7H5N C6H5CN | |
| Molar mass | 103.12 g/mol |
| Appearance | White solid |
| Odor | Almond-like |
| Density | 1.01 g/cm3 (20 °C) |
| Melting point | −13 °C (9 °F; 260 K) |
| Boiling point | 190.7 °C (375.3 °F; 463.8 K) |
| 2 g/100 ml (25 °C) | |
| Solubility | Miscible with ethanol Vvery soluble in acetone, benzene, toluene Soluble in carbon tetrachloride |
| Vapor pressure | 0.768 mmHg at 25 °C |
| Hazards | |
| Safety data sheet | Sigma-Aldrich |
| Flash point | 75 °C (167 °F; 348 K) |
| Related compounds | |
| Related compounds
|
Benzyl cyanide |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Benzonitrile is the chemical compound with the formula C6H5(CN), abbreviated PhCN.
Benzonitrile aka phenyl cyanide is NOT benzyl cyanide.
Contents
Properties
Chemical
Benzonitrile forms coordination complexes with transition metals that are both soluble in organic solvents and conveniently labile.
Physical
Benzonitrile is a colorless liquid with a sweet almond odor.
Availability
Benzonitrile is sold by chem suppliers.
Preparation
Benzonitrile can be prepared by heating a mixture of benzamide and ammonium sulfamate. The reaction produces ammonia and ammonium bisulfate as side products.[1]
Can be prepared by the dehydration of benzamide at high temperatures in the presence of catalyst. Another accessible route is reaction between cuprous cyanide or NaCN with bromobenzene in DMSO, known as Rosenmund–von Braun reaction.
Benzonitrile can be prepared by ammoxidation of toluene, that is its reaction with ammonia and oxygen (or air) at temperatures between 400-450 °C:
- C6H5CH3 + 3/2 O2 + NH3 → C6H5(CN) + 3 H2O
Projects
- Make aromatic compounds
- Make benzamide
Handling
Safety
Benzonitrile is irritant.
Storage
In closed bottles, away from light and air.
Disposal
Can be neutralized by mixing it with a flammable solvent then incinerated outside or in a fume hood.
