Benzyl cyanide
| Names | |
|---|---|
| IUPAC name
Phenylacetonitrile
| |
| Other names
2-Phenylacetonitrile
Benzeneacetonitrile Benzylnitrile Benzyl nitrile Phenylacetonitrile α-Tolunitrile | |
| Properties | |
| C8H7N C6H5CH2CN | |
| Molar mass | 117.15 g/mol |
| Appearance | Colorless oily liquid |
| Odor | Aromatic |
| Density | 1.020 g/cm3 (20 °C) |
| Melting point | −24 °C (−11 °F; 249 K) |
| Boiling point | 233.5 °C (452.3 °F; 506.6 K) |
| 0.1 g/100 ml | |
| Solubility | Miscible with acetone, diethyl ether, ethanol, isopropanol, methanol, THF |
| Vapor pressure | 0.1 mmHg (20 °C) |
| Hazards | |
| Safety data sheet | Sigma-Aldrich |
| Flash point | 102 °C (215.6 °F; 375 K) |
| Lethal dose or concentration (LD, LC): | |
| LD50 (Median dose)
|
270 mg/kg (rat, oral) |
| Related compounds | |
| Related compounds
|
Benzonitrile |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Benzyl cyanide (abbreviated BnCN) is an organic aromatic compound with the formula C6H5CH2CN.
Contents
Properties
Chemical
Hydrolysis of benzyl cyanide gives phenylacetic acid. Sulfuric acid is often used as catalyst, usually as 70% concentration.[1][2]
Physical
Benzyl cyanide is a colorless liquid, immiscible with water, but miscible with other organic solvents.
Availability
Benzyl cyanide is sold by chemical suppliers. Since it's classified as List I drug precursor in most countries, it's almost impossible to be acquired by the hobby chemist without a permit. In the United States it is classified as a DEA List I chemical.
Preparation
Benzyl cyanide can be produced via Kolbe nitrile synthesis between benzyl chloride and sodium cyanide.
- C6H5CH2Cl + NaCN → C6H5CH2CN + NaCl
Oxidative decarboxylation of phenylalanine is another possible route.
Projects
- Synthesis of various pharmaceuticals
- Preparation of phenylacetic acid
- Preparation of phenethylamine
Handling
Safety
Benzyl cyanide is irritant, though it's not very volatile. It has medium toxicity.
Storage
In closed amber glass bottles, away from light and air.
Disposal
Can be mixed with a more flammable solvent and burned.
References
- ↑ Perfumery Essent. Oil Record 14, 336 (1924)
- ↑ https://erowid.org/archive/rhodium/chemistry/phenylacetic.html
