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185558

Sigma-Aldrich

Benzyl chloride

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

Synonym(s):

α-Chlorotoluene

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About This Item

Linear Formula:
C6H5CH2Cl
CAS Number:
100-44-7
Molecular Weight:
126.58
Beilstein:
471308
MDL number:
MFCD00000889
UNSPSC Code:
12352300
eCl@ss:
39050202
PubChem Substance ID:
24851148
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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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

Signal Word

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

Heart,forestomach, Respiratory system

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

152.6 °F - closed cup

Flash Point(C)

67 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Benzylation of benzene by benzyl chloride over iron mesoporous molecular sieves materials
Bachari K, et al.
J. Catal., 221(1), 55-61 (2004)
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)
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)
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)
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