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| Names | |||
|---|---|---|---|
| Preferred IUPAC name (Chloromethyl)benzene | |||
| Other names α-Chlorotoluene Benzyl chloride alpha-chlorophenylmethane | |||
| Identifiers | |||
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3D model (JSmol) | |||
| Abbreviations | BnCl | ||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider |
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| ECHA InfoCard | 100.002.594 | ||
| EC Number |
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| KEGG |
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| UNII | |||
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| Properties | |||
| C7H7Cl | |||
| Molar mass | 126.58 g·mol−1 | ||
| Appearance | Colorless to slightlyyellow,toxic liquid | ||
| Odor | Pungent, aromatic[1] | ||
| 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)[1] | |||
| Solubility | soluble inethanol,ethyl ether,chloroform,CCl4 miscible in organic solvents | ||
| Vapor pressure | 1 mmHg (20 °C)[1] | ||
| −81.98·10−6 cm3/mol | |||
Refractive index (nD) | 1.5415 (15 °C) | ||
| Hazards | |||
| Occupational safety and health (OHS/OSH): | |||
Main hazards | Toxic andcarcinogenic; lachrymator | ||
| NFPA 704 (fire diamond) | |||
| Flash point | 67 °C (153 °F; 340 K) | ||
| 585 °C (1,085 °F; 858 K) | |||
| Explosive limits | ≥1.1%[1] | ||
| Lethal dose or concentration (LD, LC): | |||
LD50 (median dose) | 121 mg/kg (rat, oral) | ||
LC50 (median concentration) | 150 ppm (rat, 2 hr) 80 ppm (mouse, 2 hr)[2] | ||
LCLo (lowest published) | 380 ppm (dog, 8 hr)[2] | ||
| NIOSH (US health exposure limits): | |||
PEL (Permissible) | TWA 1 ppm (5 mg/m3)[1] | ||
REL (Recommended) | C 1 ppm (5 mg/m3) [15-minute][1] | ||
IDLH (Immediate danger) | 10 ppm[1] | ||
| Safety data sheet (SDS) | External MSDS | ||
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
Benzyl chloride, orα-chlorotoluene, is anorganic compound with theformulaC6H5CH2Cl. This colorless liquid is areactiveorganochlorine compound that is a widely usedchemical building block.
Benzyl chloride is prepared industrially by thegas-phasephotochemical reaction oftoluene withchlorine:[3]
In this way, approximately 100,000 tonnes are produced annually. The reaction proceeds by thefree radical process, involving the intermediacy of free chlorine atoms.[4] Side products of the reaction includebenzal chloride andbenzotrichloride.
Other methods of production exist, such as theBlanc chloromethylation ofbenzene. Benzyl chloride was first prepared from treatment ofbenzyl alcohol withhydrochloric acid.
Industrially, benzyl chloride is theprecursor to benzyl esters, which are used asplasticizers, flavorants, andperfumes.Phenylacetic acid, a precursor to pharmaceuticals, is produced frombenzyl cyanide, which in turn is generated by treatment of benzyl chloride withsodium cyanide.Quaternary ammonium salts, used assurfactants, are readily formed by alkylation oftertiary amines with benzyl chloride.[3]
Benzyl ethers are often derived from benzyl chloride. Benzyl chloride reacts with aqueous sodium hydroxide to givedibenzyl ether. Inorganic synthesis, benzyl chloride is used to introduce thebenzylprotecting group in reaction withalcohols, 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 alkalineKMnO4:
Benzyl chloride may be used in the synthesis of amphetamine-class drugs, and for this reason, sales of benzyl chloride are monitored as aList II drug precursor chemical by the USDrug Enforcement Administration.
Benzyl chloride also reacts readily with metallicmagnesium to produce aGrignard reagent.[5] It is preferable overbenzyl bromide for the preparation of this reagent, since the reaction of the bromide with magnesium tends to form theWurtz coupling product1,2-diphenylethane.
Benzyl chloride is analkylating agent. Indicative of its high reactivity (relative to alkyl chlorides), benzyl chloride slowly reacts with water in ahydrolysis reaction to formbenzyl alcohol andhydrochloric acid. In contact with mucous membranes, hydrolysis produces hydrochloric acid. Thus, benzyl chloride is alachrymator and has been used inchemical warfare.[6] It is also very irritating to the skin.
It is classified as anextremely hazardous substance in the United States as defined in Section 302 of the U.S.Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.[7]
