B17905

Sigma-Aldrich

Benzyl bromide

reagent grade, 98%

Synonym(s):
α-Bromotoluene
Linear Formula:
C6H5CH2Br
CAS Number:
Molecular Weight:
171.03
Beilstein/REAXYS Number:
385801
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

grade

reagent grade

vapor density

5.8 (vs air)

assay

98%

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.

Packaging

25, 100, 500 g in glass bottle
2.5 kg in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 1737 8(6.1) / PGII

WGK Germany

WGK 2

Flash Point(F)

186.8 °F - closed cup

Flash Point(C)

86 °C - closed cup

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...
A novel acid-catalyzed O-benzylating reagent with the smallest unit of imidate structure.
Yamada K
Organic Letters, 14(19), 5026-5029 (2012)
Giuseppe Belletti et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 26(4), 839-844 (2019-10-31)
Viedma ripening is a deracemization process that has been used to deracemize a range of chiral molecules. The method has two major requirements: the compound needs to crystallize as a conglomerate and it needs to be racemizable under the crystallization...
Rate constants for reaction of 1, 2-dimethylimidazole with benzyl bromide in ionic liquids and organic solvents.
Skrzypczak A and Neta P.
International Journal of Chemical Kinetics, 36(4), 253-258 (2004)
Hon Man Yau et al.
Molecules (Basel, Switzerland), 14(7), 2521-2534 (2009-07-28)
While there has been much effort in recent years to characterise ionic liquids in terms of parameters that are well described for molecular solvents, using these to explain reaction outcomes remains problematic. Herein we propose that many reaction outcomes in...

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