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187070

Sigma-Aldrich

2-Bromobenzyl bromide

98%

Synonym(s):

α,2-Dibromotoluene

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About This Item

Linear Formula:
BrC6H4CH2Br
CAS Number:
3433-80-5
Molecular Weight:
249.93
Beilstein/REAXYS Number:
971015
EC Number:
222-334-8
MDL number:
MFCD00000173
UNSPSC Code:
12352100
PubChem Substance ID:
24851250
NACRES:
NA.22

Quality Level

100

assay

98%

form

solid

refractive index

n20/D 1.619 (lit.)

bp

129 °C/19 mmHg (lit.)

mp

29-32 °C (lit.)

solubility

dioxane: soluble 1 g/10 mL, clear, colorless

functional group

bromo

SMILES string

BrCc1ccccc1Br

InChI

1S/C7H6Br2/c8-5-6-3-1-2-4-7(6)9/h1-4H,5H2

InChI key

LZSYGJNFCREHMD-UHFFFAOYSA-N

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General description

2-Bromobenzyl bromide is a reagent used to protect ketones and aldehydes in their less reactive alcohol oxidation states and as a coupling component in various reactions.

Application

2-Bromobenzyl bromide was used in the synthesis of:
  • substituted quinazolines and 1,2,3,4-tetrahydroquinazolines
  • 2- and 3-substituted indenes
  • tris-2-bromotribenzylamine

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

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Synthesis and structural studies of tris-2-chlorobenzylamine and tris-2-bromobenzylamine.
Chen Q, , et al.
Journal of Chemical Crystallography, 35(3), 177-181 (2005)
Efficient synthesis of 2-and 3-substituted indenes from 2-bromobenzyl bromide through an enolate alkylation/Cr (II)/Ni (II)-mediated carbonyl addition sequence.
Halterman RLand Zhu C.
Tetrahedron Letters, 40(42), 7445-7448 (1999)
2-Bromobenzyl Bromide
Pfeifer LA
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
Xuesen Fan et al.
Chemistry, an Asian journal, 9(3), 739-743 (2014-01-01)
An efficient synthesis of diversely substituted quinazolines and 1,2,3,4-tetrahydroquinazolines through copper-catalyzed tandem reactions of the readily available 2-bromobenzyl bromides, aldehydes, and aqueous ammonia or amines has been developed. By using ammonia and simple aliphatic amines as the nitrogen source, the
Prachi Singh et al.
SLAS discovery : advancing life sciences R & D, 22(4), 440-446 (2017-03-23)
Analysis of interactions between molecules is of fundamental importance in life science research. In this study, we applied weak affinity chromatography, based on high-performance liquid chromatography and mass spectrometry, as a powerful tool for direct analysis of the components of
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