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B17905

Sigma-Aldrich

Benzyl bromide

reagent grade, 98%

Synonym(s):

α-Bromotoluene

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About This Item

Linear Formula:
C6H5CH2Br
CAS Number:
100-39-0
Molecular Weight:
171.03
Beilstein:
385801
EC Number:
202-847-3
MDL number:
MFCD00000172
UNSPSC Code:
12352100
PubChem Substance ID:
24891612
NACRES:
NA.22

grade

reagent grade

Quality Level

200

vapor density

5.8 (vs air)

Assay

98%

form

liquid

impurities

≤0.5% p-bromotoluene

refractive index

n20/D 1.575 (lit.)

bp

198-199 °C (lit.)

mp

−3-−1 °C (lit.)

density

1.438 g/mL at 25 °C (lit.)

SMILES string

BrCc1ccccc1

InChI

1S/C7H7Br/c8-6-7-4-2-1-3-5-7/h1-5H,6H2

InChI key

AGEZXYOZHKGVCM-UHFFFAOYSA-N

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General description

Benzyl bromide is an aromatic halide that is mainly used as a protecting agent for protecting hydroxy group of alcohols via O-benzylation reaction.

Application

Benzyl bromide has been used as an initiator in the synthesis of poly(styrene-b-methylmethacrylate) copolymers by atom transfer radical polymerization. It can undergo Menschutkin reaction with 1, 2-dimethylimidazole to form 3-benzyl-1, 2-dimethylimidazolium bromide.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

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

WGK

WGK 2

Flash Point(F)

186.8 °F - closed cup

Flash Point(C)

86 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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A novel acid-catalyzed O-benzylating reagent with the smallest unit of imidate structure.
Yamada K
Organic Letters, 14(19), 5026-5029 (2012)
Yukiko Fujii et al.
Environmental pollution (Barking, Essex : 1987), 247, 312-318 (2019-01-28)
We investigated the profiles and levels of perfluoroalkyl carboxylic acid (PFCA) contamination in Pacific cod (Gadus macrocephalus) from the North Pacific Ocean. The mean concentrations of PFCAs containing 8 to 14 carbon atoms (C8-C14) in edible Pacific cod muscle ranged
Vanderlisa Rita Meleti et al.
Acta tropica, 202, 105248-105248 (2019-11-05)
This paper reports the synthesis of (±)-licarin A 1, a dihydrobenzofuran neolignan, resultant of an oxidative coupling reaction of isoeugenol and horseradish peroxidase (HRP) enzyme. Following, three semi-synthetic derivatives from this compound were obtained: benzylated (±)-licarin A 2, methylated (±)-licarin
Simon J Mountford et al.
Organic & biomolecular chemistry, 15(34), 7173-7180 (2017-08-16)
The first total synthesis of a polypeptin, PE2, as well as its solution structure is reported. Synthesis in optically pure form confirms the proposed stereochemistry of the polypeptins at the 3-position on the 3-hydroxy depsipeptide moiety. We have also determined
Wing-Yiu Yu et al.
Organic letters, 11(2), 469-472 (2008-12-23)
A Pd-catalyzed cross-coupling reaction of benzyl bromides with alpha-aryldiazoesters is described, and E-alpha,beta-diarylacrylates were obtained in good yields and excellent E-to-Z selectivity (>20:1).
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