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185558

Sigma-Aldrich

Benzyl chloride

ReagentPlus®, 99%, contains ≤1% propylene oxide as stabilizer

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Synonym(s):
α-Chlorotoluene
Linear Formula:
C6H5CH2Cl
CAS Number:
Molecular Weight:
126.58
Beilstein/REAXYS Number:
471308
MDL number:
eCl@ss:
39050202
PubChem Substance ID:
NACRES:
NA.22

vapor density

4.36 (vs air)

vapor pressure

10.3 mmHg ( 60 °C)
7 mmHg ( 55 °C)

product line

ReagentPlus®

assay

99%

form

liquid

autoignition temp.

1085 °F

contains

≤1% propylene oxide as stabilizer

expl. lim.

14 %

refractive index

n20/D 1.538 (lit.)

bp

177-181 °C (lit.)

mp

−43 °C (lit.)

solubility

0.46 g/L at 30 °C (Decomposes in contact with water)

density

1.1 g/mL at 25 °C (lit.)

SMILES string

ClCc1ccccc1

InChI

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

InChI key

KCXMKQUNVWSEMD-UHFFFAOYSA-N

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1 of 4

This Item
2599508.018098.01804
vibrant-m

185558

Benzyl chloride

vibrant-m

259950

Benzoyl chloride

vibrant-m

8.01809

Benzyl chloride

vibrant-m

8.01804

Benzoyl chloride

solubility

0.46 g/L at 30 °C (Decomposes in contact with water)

solubility

-

solubility

460 mg/L

solubility

-

assay

99%

assay

98.0-100.5%, 99%

assay

≥99.0% (GC)

assay

≥99.0% (GC)

bp

177-181 °C (lit.)

bp

198 °C (lit.)

bp

179.3 °C/1013 hPa

bp

197.2 °C/1013 hPa

form

liquid

form

liquid

form

liquid

form

liquid

mp

−43 °C (lit.)

mp

−1 °C (lit.)

mp

-39 °C

mp

-0.6 °C

General description

Benzyl chloride (BnCl) is an organochlorine compound, which is widely used in organic synthesis for the preparation of useful chemical building blocks.

Application

Benzyl chloride can be used as:
  • A benzylating agent for the benzylation of benzene and other aromatic compounds.
  • A reactant for the preparation of 4-methoxydiphenylmethane by Friedel-Crafts alkylation with anisole.

It can also be used to introduce the benzyl protecting group to alcohols and carboxylic acids by forming corresponding benzyl ether, and benzyl ester, respectively.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

signalword

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Carc. 1B - Eye Dam. 1 - Muta. 1B - Skin Irrit. 2 - Skin Sens. 1 - STOT RE 2 Oral - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

152.6 °F

flash_point_c

67 °C

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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Heterogeneous phase alkylation of phenols making use of phase transfer catalysis and microwave irradiation
Keglevich G, et al.
Letters in Organic Chemistry, 6(7), 535-539 (2009)
Benzylation of toluene by benzyl chloride over protonic zeolites.
Coq B, et al.
Applied Catalysis A: General, 100(1), 69-75 (1993)
Benzylation of benzene and other aromatics by benzyl chloride over mesoporous AlSBA-15 catalysts.
Vinu A.,e et al.
Microporous and Mesoporous Materials : The Official Journal of the International Zeolite Association, 80(1-3), 195-203 (2005)
Benzylation of benzene by benzyl chloride over iron mesoporous molecular sieves materials
Bachari K, et al.
J. Catal., 221(1), 55-61 (2004)
Design and performance of supported Lewis acid catalysts derived from metal contaminated biomass for Friedel-Crafts alkylation and acylation
Losfeld G, et al.
Catalysis Today, 189(1), 111-116 (2012)

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