Benzyl chloride
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Names | |||
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Preferred IUPAC name
(Chloromethyl)benzene | |||
Other names
α-Chlorotoluene
Benzyl chloride alpha-chlorophenylmethane | |||
Identifiers | |||
3D model (
JSmol ) |
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Abbreviations | BnCl | ||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard
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100.002.594 | ||
EC Number |
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KEGG | |||
PubChem CID
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UNII | |||
CompTox Dashboard (EPA)
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Properties | |||
C7H7Cl | |||
Molar mass | 126.58 g·mol−1 | ||
Appearance | Colorless to slightly toxic liquid
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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 in ethyl ether, chloroform, CCl4 miscible in organic solvents | ||
Vapor pressure | 1 mmHg (20 °C)[1] | ||
-81.98·10−6 cm3/mol | |||
Refractive index (nD)
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1.5415 (15 °C) | ||
Hazards | |||
Occupational safety and health (OHS/OSH): | |||
Main hazards
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Toxic and carcinogenic ; lachrymator
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NFPA 704 (fire diamond) | |||
Flash point | 67 °C (153 °F; 340 K) | ||
585 °C (1,085 °F; 858 K) | |||
Explosive limits
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≥1.1%[1] | ||
Lethal dose or concentration (LD, LC): | |||
LD50 (median dose)
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121 mg/kg (rat, oral) | ||
LC50 (median concentration)
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150 ppm (rat, 2 hr) 80 ppm (mouse, 2 hr)[2] | ||
LCLo (lowest published)
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380 ppm (dog, 8 hr)[2] | ||
NIOSH (US health exposure limits): | |||
PEL (Permissible)
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TWA 1 ppm (5 mg/m3)[1] | ||
REL (Recommended)
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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 their standard state (at 25 °C [77 °F], 100 kPa).
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Benzyl chloride, or α-chlorotoluene, is an
Preparation
Benzyl chloride is prepared industrially by the
- C6H5CH3 + Cl2 → C6H5CH2Cl + HCl
In this way, approximately 100,000 tonnes are produced annually. The reaction proceeds by the
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.
Uses and reactions
Industrially, benzyl chloride is the
Benzyl ethers are often derived from benzyl chloride. Benzyl chloride reacts with aqueous sodium hydroxide to give
Benzoic acid (C6H5COOH) can be prepared by oxidation of benzyl chloride in the presence of alkaline KMnO4:
- C6H5CH2Cl + 2 KOH + 2 [O] → C6H5COOK + KCl + H2O
Benzyl chloride may be used in the synthesis of amphetamine-class drugs, and for this reason, sales of benzyl chloride are monitored as a List II drug precursor chemical by the US Drug Enforcement Administration.
Benzyl chloride also reacts readily with metallic
Safety
Benzyl chloride is an
It is classified as an
See also
References
- ^ a b c d e f g NIOSH Pocket Guide to Chemical Hazards. "#0053". National Institute for Occupational Safety and Health (NIOSH).
- ^ a b "Benzyl chloride". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
- ^ ISBN 978-3527306732.
- ISBN 0-582-46236-3
- ^ Henry Gilman and W. E. Catlin (1941). "n-Propylbenzene". Organic Syntheses; Collected Volumes, vol. 1, p. 471.
- ^ "40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" (PDF) (July 1, 2008 ed.). Government Printing Office. Archived from the original (PDF) on February 25, 2012. Retrieved October 29, 2011.
External links
- International Chemical Safety Card 0016
- SIDS Initial Assessment Report for benzyl chloride from the Organisation for Economic Co-operation and Development(OECD)
- CDC - NIOSH Pocket Guide for Chemical Hazards - Benzyl chloride