Benzyl chloride
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| Names | |||
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Preferred IUPAC name
(Chloromethyl)benzene
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| Other names
α-Chlorotoluene
Benzyl chloride |
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| Identifiers | |||
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3D model (Jmol)
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| Abbreviations | BnCl | ||
| ChEBI | |||
| ChemSpider | |||
| ECHA InfoCard | 100.002.594 | ||
| EC Number | 202-853-6 | ||
| KEGG | |||
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PubChem CID
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| UNII | |||
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| Properties | |||
| C7H7Cl | |||
| Molar mass | 126.58 g/mol | ||
| Appearance | colorless to slightly yellow liquid | ||
| Odor | pungent, aromatic | ||
| Density | 1.100 g/cm3 | ||
| Melting point | −39 °C (−38 °F; 234 K) | ||
| Boiling point | 179 °C (354 °F; 452 K) | ||
| very slightly soluble (0.05% at 20 °C) | |||
| Solubility | soluble in ethanol, ethyl ether, chloroform, CCl4 miscible in organic solvents |
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| Vapor pressure | 1 mmHg (20 °C) | ||
| -81.98·10−6 cm3/mol | |||
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Refractive index (nD)
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1.5415 (15 °C) | ||
| Hazards | |||
| Safety data sheet | External MSDS | ||
| NFPA 704 | |||
| Flash point | 67 °C (153 °F; 340 K) | ||
| 585 °C (1,085 °F; 858 K) | |||
| Explosive limits | ≥1.1% | ||
| Lethal dose or concentration (LD, LC): | |||
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LD50 (median dose)
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1231 mg/kg (rat, oral) | ||
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LC50 (median concentration)
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150 ppm (rat, 2 hr) 80 ppm (mouse, 2 hr) |
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LCLo (lowest published)
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380 ppm (dog, 8 hr) | ||
| US health exposure limits (NIOSH): | |||
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PEL (Permissible)
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TWA 1 ppm (5 mg/m3) | ||
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REL (Recommended)
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C 1 ppm (5 mg/m3) [15-minute] | ||
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IDLH (Immediate danger)
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10 ppm | ||
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is   ?) |
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| Infobox references | |||
Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula C6H5CH2Cl. This colourless liquid is a reactive organochlorine compound that is a widely used chemical building block.
Benzyl chloride is prepared industrially by the gas-phase reaction of toluene with chlorine:
In this way, approximately 100,000 tonnes are produced annually. The reaction proceeds by the free radical process, involving the intermediacy of free chlorine atoms. Side products of the reaction include benzal chloride and benzotrichloride.
Other methods of production exist, such as the Blanc chloromethylation of benzene. Benzyl chloride was first prepared from treatment of benzyl alcohol with hydrochloric acid.
Industrially, benzyl chloride is the precursor to benzyl esters which are used as plasticizers, flavorants, and perfumes. Phenylacetic acid, a precursor to pharmaceuticals, is produced from benzyl cyanide, which is generated by treatment of benzyl chloride with sodium cyanide. Quaternary ammonium salts, used as surfactants, are readily formed by alkylation of tertiary amines with benzyl chloride.
In organic synthesis, benzyl chloride is used for the introduction of the benzyl protecting group in reaction with alcohols, yielding the corresponding benzyl ether, carboxylic acids, and benzyl ester. Benzoic acid (C6H5COOH) can be prepared by oxidation of benzyl chloride in the presence of alkaline KMnO4:
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