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185558

Sigma-Aldrich

Benzyl chloride

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

Sinónimos:

α-Chlorotoluene

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About This Item

Fórmula lineal:
C6H5CH2Cl
Número de CAS:
100-44-7
Peso molecular:
126.58
Beilstein/REAXYS Number:
471308
MDL number:
MFCD00000889
UNSPSC Code:
12352300
eCl@ss:
39050202
PubChem Substance ID:
24851148
NACRES:
NA.22

vapor density

4.36 (vs air)

Quality Level

200

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

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

Heart,forestomach, 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 - closed cup

flash_point_c

67 °C - closed cup

ppe

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

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Certificados de análisis (COA)

Lot/Batch Number
SLCL0249
MKCP5632
MKCM5986
MKCM2302
MKCM2298

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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)
Benzylation of toluene by benzyl chloride over protonic zeolites.
Coq B, et al.
Applied Catalysis A: General, 100(1), 69-75 (1993)
Alireza Ariafard et al.
Journal of the American Chemical Society, 128(39), 13010-13016 (2006-09-28)
The reaction mechanism of the Pd-catalyzed benzyl/allyl coupling of benzyl chloride with allyltributylstannan, resulting in the dearomatization of the benzyl group, was studied using density functional theory calculations at the B3LYP level. The calculations indicate that the intermediate (eta(3)-benzyl)(eta(1)-allyl)Pd(PH(3)) is
An Wang et al.
Journal of the American Chemical Society, 132(28), 9534-9536 (2010-06-26)
Aiming to deeply understand the electrocatalytic mechanism of silver on reduction of benzyl chloride, we carried out an in situ electrochemical surface-enhanced Raman spectroscopic study to characterize various surface species in different electrode potential regions. A further analysis with DFT
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