Benzyl chloride

Details

Stereochemistry	ACHIRAL
Molecular Formula	C7H7Cl
Molecular Weight	126.583
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

ClCC1=CC=CC=C1

InChI

InChIKey=KCXMKQUNVWSEMD-UHFFFAOYSA-N

InChI=1S/C7H7Cl/c8-6-7-4-2-1-3-5-7/h1-5H,6H2

HIDE SMILES / InChI

Molecular Formula	C7H7Cl
Molecular Weight	126.583
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23939874 | https://www.ncbi.nlm.nih.gov/pubmed/6358331 | https://www.ncbi.nlm.nih.gov/pubmed/6635615 | https://www.ncbi.nlm.nih.gov/pubmed/791819

Benzyl chloride, or α-chlorotoluene, is a reactive organochlorine compound that is a widely used chemical building block. 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. Benzyl chloride is an alkylating agent with very irritating properties to the skin. Indicative of its high reactivity (relative to alkyl chlorides), benzyl chloride reacts with water in a hydrolysis reaction to form benzyl alcohol and hydrochloric acid. In contact with mucous membranes, hydrolysis produces hydrochloric acid. Thus, benzyl chloride is a lachrymator and has been used in chemical warfare.

Approval Year

PubMed

Title	Date	PubMed
Synthesis and analgesic activity of some 1-benzyl-2-substituted-4,5-diphenyl-1H-imidazole derivatives.	2001 Apr	11421256
Synthesis, DNA-binding activity and cytotoxicity of carbamate derivatives of Hoechst 33258 in breast cancer MCF-7 cells.	2002 Jul	12132669
Benzylation of aromatic compounds with different crystallites of MgO.	2003 Feb 26	12590509
Triamidotriazacyclononane complexes of group 3 metals. Synthesis and crystal structures.	2003 Jun 30	12817984
Determination of aliphatic alcohols after on-line microwave-assisted derivatization by liquid chromatography-photodiode array detection.	2004 Dec 15	18969749
Mixture toxicity of reactive chemicals by using two bacterial growth assays as indicators of protein and DNA damage.	2005 Nov 15	16323773
Ultrafast spectroscopic study of the photochemistry and photophysics of arylhalodiazirines: direct observation of carbene and zwitterion formation.	2006 Dec 27	17177362
EcoScale, a semi-quantitative tool to select an organic preparation based on economical and ecological parameters.	2006 Mar 3	16542013
Amino benzoic acid modified silica--an improved catalyst for the mono-substituted product in the benzylation of toluene with benzyl chloride.	2007 Jul 1	17391688
Surface-imprinted core-shell nanoparticles for sorbent assays.	2007 Jul 15	17563116
Synthesis, Characterization, and In Vitro Photodynamic Activity of Novel Amphiphilic Zinc(II) Phthalocyanines Bearing Oxyethylene-Rich Substituents.	2008	18288246
Synthesis of functional cubes from octavinylsilsesquioxane (OVS).	2008 Dec 21	19039377
2-(1,3-Dibenzyl-imidazolidin-2-yl-idene)malononitrile.	2008 May 21	21202631
Adsorption and desorption of phosphate and nitrate ions using quaternary (polypropylene-g-N,N-dimethylamino ethylmethacrylate) graft copolymer.	2008 Nov 30	18367330
Aromatic ortho-benzylation reveals an unexpected reductant.	2008 Nov 6	18839963
Synthesis of chlorovinyl sulfones as structural analogs of chalcones and their antiplasmodial activities.	2009 Apr	19036479
Bond activation, substrate addition and catalysis by an isolable two-coordinate Pd(0) bis-isocyanide monomer.	2009 Aug 19	19630396
Analysis of residual products in benzyl chloride used for the industrial synthesis of quaternary compounds by liquid chromatography with diode-array detection.	2009 Feb	19222920
Structures of copper complexes of the hybrid [SNS] ligand of bis(2-(benzylthio)ethyl)amine and facile catalytic formation of 1-benzyl-4-phenyl-1H-1,2,3-triazole through click reaction.	2009 Feb 2	19123783
Characterization of the chronic risk and hazard of hazardous air pollutants in the United States using ambient monitoring data.	2009 May	19479023
Diversification of a thieno[2,3-d]pyrimidin-4-one scaffold via regioselective alkylation reactions.	2009 May-Jun	19385601
Simple mixed Fe-Zn catalysts for the Suzuki couplings of tetraarylborates with benzyl halides and 2-halopyridines.	2009 Nov 14	19841799
N-Benzyl-N-cyclo-hexyl-4-methyl-benzene-sulfonamide.	2009 Nov 18	21578835
Dichloridobis(4-chloro-benz-yl)(4,4'-dimethyl-2,2'-bipyridine-κN,N')tin(IV).	2009 Nov 25	21578683
1-Benzyl-3-phenyl-quinoxalin-2(1H)-one.	2009 Oct 10	21578291
Benzyl 2-ethyl-hexyl sulfoxide.	2009 Oct 31	21578506
Dichloridoocta-kis(2-chloro-benz-yl)di-μ(2)-hydroxido-di-μ(3)-oxido-tetra-tin(IV).	2009 Oct 31	21578215
An ortho-rhom-bic polymorph of 1-benzyl-1H-benzimidazole.	2010 Apr 28	21579238
Phenylhydroxycarbene.	2010 Jun 2	20462194
High-throughput production of high-quality graphene by exfoliation of expanded graphite in simple liquid benzene derivatives.	2010 Nov	21137940
Removal of hexavalent chromium by new quaternized crosslinked poly(4-vinylpyridines).	2010 Nov 15	20692089

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:55:25 GMT 2025` Edited by `admin` on `Mon Mar 31 17:55:25 GMT 2025`
Record UNII	83H19HW7K6
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Benzyl chloride

Systematic Name

English

NSC-8043

Preferred Name

English

Benzyl chloride [MI]

Common Name

English

Tolyl chloride

Systematic Name

English

Benzyl chloride [USP-RS]

Common Name

English

Benzyl chloride [HSDB]

Common Name

English

?-Chlorotoluene

Systematic Name

English

Benzalkonium chloride impurity C [EP IMPURITY]

Common Name

English

Benzyl chloride [II]

Common Name

English

Toluene, ?-chloro-

Systematic Name

English

1-Chloromethylbenzene

Systematic Name

English

Phenylmethyl chloride

Systematic Name

English

Classification Tree Code System Code

DEA NO.

8570