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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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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
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).
Ke Gao et al.
The Journal of organic chemistry, 72(22), 8611-8613 (2007-10-09)
A multicomponent one-pot reaction of 2-alkynylbenzaldehydes, amines, zinc, and allylic bromide or benzyl bromide using the combination of Mg(ClO4)2/Cu(OTf)2 as catalyst in THF/DCE (1:20) is described, which provides an efficient and practical route for the synthesis of functionalized 1,2-dihydroisoquinolines.
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
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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