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
Dibenzyl sulfoxide.	2010-12-18	21522682
{2-[(Benzo-yloxy)meth-yl]-1-oxo-3H-pyrrolizin-2-yl}methyl benzoate.	2010-12-18	21522679
Removal of hexavalent chromium by new quaternized crosslinked poly(4-vinylpyridines).	2010-11-15	20692089
High-throughput production of high-quality graphene by exfoliation of expanded graphite in simple liquid benzene derivatives.	2010-11	21137940
BODIPY-based chain transfer agent: reversibly thermoswitchable luminescent gold nanoparticle stabilized by BODIPY-terminated water-soluble polymer.	2010-10-05	20815359
Effect of saliva processing on bacterial DNA extraction.	2010-10	21213596
Ab initio HF and DFT simulations, FT-IR and FT-Raman vibrational analysis of alpha-chlorotoluene.	2010-09-15	20537941
Highly efficient palladium precatalysts of homoscorpionate bispyrazolyl ligands for the more challenging Suzuki-Miyaura cross-coupling of aryl chlorides.	2010-08-21	20607167
In situ identification of intermediates of benzyl chloride reduction at a silver electrode by SERS coupled with DFT calculations.	2010-07-21	20575538
Palladium nanoparticle catalyzed Hiyama coupling reaction of benzyl halides.	2010-06-18	20491503
Phenylhydroxycarbene.	2010-06-02	20462194
Rapid and effective DNA extraction method with bead grinding for a large amount of fungal DNA.	2010-06	20537263
N,N-Dibenzyl-4-methyl-benzene-sulfonamide.	2010-04-30	21579245
An ortho-rhom-bic polymorph of 1-benzyl-1H-benzimidazole.	2010-04-28	21579238
N-Benzyl-N-methyl-3-phenyl-3-[4-(tri-fluoro-meth-yl)phen-oxy]propanamine (N-benzylflouoxetine).	2010-04-24	21579194
9-Benzyl-9H-carbazole.	2010-04-14	21579131
4-Benzyl-6-bromo-2-phenyl-4H-imidazo[4,5-b]pyridine.	2010-03-27	21580750
Discovery of 4-amino-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamides as selective, orally active inhibitors of protein kinase B (Akt).	2010-03-11	20151677
1,3-Dibenzyl-6-bromo-1H-imidazo[4,5-b]pyridin-2(3H)-one.	2010-03-06	21580599
{[(N-Butyl-N-methylcarbamothioyl)sulfanyl]acetato-κO}tris(2-chloro-benz-yl)tin(IV).	2010-02-17	21580249
1,3-Dibenzyl-2-methyl-benzimidazolium chloride.	2010-01-27	21579870
1-Benzyl-3-methyl-imidazolium chloride 0.25-hydrate.	2009-12-19	21580102
Dichloridobis(4-chloro-benz-yl)(4,4'-dimethyl-2,2'-bipyridine-κN,N')tin(IV).	2009-11-25	21578683
Antiplasmodial activities of homogentisic acid derivative protein kinase inhibitors isolated from a Vanuatu marine sponge Pseudoceratina sp.	2009-11-23	20098604
Effect of ionic liquids on the Menschutkin reaction: an experimental and theoretical study.	2009-11-20	19908910
N-Benzyl-N-cyclo-hexyl-4-methyl-benzene-sulfonamide.	2009-11-18	21578835
Simple mixed Fe-Zn catalysts for the Suzuki couplings of tetraarylborates with benzyl halides and 2-halopyridines.	2009-11-14	19841799
N-Benzyl-N-cyclo-hexyl-benzene-sulfonamide.	2009-11-11	21578785
Benzyl 2-ethyl-hexyl sulfoxide.	2009-10-31	21578506
Dichloridoocta-kis(2-chloro-benz-yl)di-μ(2)-hydroxido-di-μ(3)-oxido-tetra-tin(IV).	2009-10-31	21578215
1-Benzyl-3-phenyl-quinoxalin-2(1H)-one.	2009-10-10	21578291
Catalytic dehydrative etherification and chlorination of benzyl alcohols in ionic liquids.	2009-09-14	20448983
Inter-laboratory evaluation of the bioluminescent Salmonella reverse mutation assay using 10 model chemicals.	2009-09	19581339
Bond activation, substrate addition and catalysis by an isolable two-coordinate Pd(0) bis-isocyanide monomer.	2009-08-19	19630396
The photoionisation of two phenylcarbenes and their diazirine precursors investigated using synchrotron radiation.	2009-07-14	19551206
Characterization of the chronic risk and hazard of hazardous air pollutants in the United States using ambient monitoring data.	2009-05	19479023
Diversification of a thieno[2,3-d]pyrimidin-4-one scaffold via regioselective alkylation reactions.	2009-04-24	19385601
Ultrafast dynamics of isolated phenylcarbenes followed by femtosecond time-resolved velocity map imaging.	2009-04-02	19245233
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.	2009-02-02	19123783
Analysis of residual products in benzyl chloride used for the industrial synthesis of quaternary compounds by liquid chromatography with diode-array detection.	2009-02	19222920
Reproducible RNA preparation from sugarcane and citrus for functional genomic applications.	2009	20148085
Synthesis of functional cubes from octavinylsilsesquioxane (OVS).	2008-12-21	19039377
Bazedoxifene for the prevention of postmenopausal osteoporosis.	2008-12	19337430
2-(1,3-Dibenzyl-imidazolidin-2-yl-idene)malononitrile.	2008-05-21	21202631
2-(Benzyl-sulfan-yl)pyridine N-oxide.	2008-04-26	21202409
1-Benzyl-3-(2-furylmeth-yl)-1,2,3,4,5,6-hexa-hydro-spiro-[benzo[h]quinazoline-5,1'-cyclo-hexa-ne]-2,4-dione.	2008-03-29	21202138
1,4-Bis(benz-yloxy)-2-tert-butyl-benzene.	2008-02-22	21201954
A Direct Method to Isolate DNA from Phyllosphere Microbial Communities without Disrupting Leaf Tissues.	2008	21558716
Triethyl-ammonium N'-(benzyl-sulfanylthio-carbonyl)-2-hydroxy-benzohydrazidate.	2007-12-21	21200900
N-Benzyl-N-(4-chloro-phen-yl)acrylamide.	2007-12-06	21200771

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