Skip to Content
MilliporeSigma
All Photos(1)

Documents

558958

Sigma-Aldrich

4-Chlorobenzyl bromide

97%

Synonym(s):

α-Bromo-p-chlorotoluene, 1-(Bromomethyl)-4-chlorobenzene, 1-Chloro-4-bromomethylbenzene, p-Chlorobenzyl bromide

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
ClC6H4CH2Br
CAS Number:
622-95-7
Molecular Weight:
205.48
EC Number:
210-760-7
MDL number:
MFCD00040714
UNSPSC Code:
12352100
PubChem Substance ID:
24879785
NACRES:
NA.22

assay

97%

form

solid

mp

48-52 °C (lit.)

SMILES string

Clc1ccc(CBr)cc1

InChI

1S/C7H6BrCl/c8-5-6-1-3-7(9)4-2-6/h1-4H,5H2

InChI key

KQNBRMUBPRGXSL-UHFFFAOYSA-N

General description

4-Chlorobenzyl bromide undergoes carbonylation in the presence of dimer of chloro(1,5-cyclooctadiene)rhodium(I) to yield the corresponding phenylacetic acid. It can be synthesized by reacting 4-chlorobenzyl alcohol with bromodimethylsulfonium bromide (BDMS) It can also be synthesized by refluxing a mixture of 4-chlorobenzaldehyde, chlorotrimethylsilane, 1,1,3,3-tetramethyldisiloxane and lithium bromide.

Application

4-Chlorobenzyl bromide may be used to synthesize 1-(4-chlorobenzyl)-2-(pyrrolidin-1-yl-methyl)-1H-benzimidazole dihydrochloride

Packaging

4-Chlorobenzyl bromide may be used to synthesize:
  • 1-[1-[2-[(4-chlorobenzyl)thio]phenyl]vinyl]-1H-imidazole
  • 6-[4-(4-chlorobenzyl)piperazinyl]chromane
  • N,N′-bis(4-chlorobenzyl)piperazine
  • N-(4-chlorobenzyl)piperazine

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Gazi S and Ananthakrishnan R
Royal Society of Chemistry Advances, 2(20), 7781- 7787 (2012)
Synthesis and antifungal activity of new 1-vinylimidazoles.
Ogata M, et al.
Journal of Medicinal Chemistry, 30(8), 1348-1354 (1987)
Synthesis of phenylacetic acids under rhodium-catalyzed carbonylation conditions.
Giroux A, et al.
Tetrahedron Letters, 41(40), 7601-7604 (2000)
Gas-phase chemistry of benzyl cations in dissociation of N-benzylammonium and N-benzyliminium ions studied by mass spectrometry.
Chai Y, et al.
Journal of the American Society For Mass Spectrometry, 23(5), 823-833 (2012)
"Reduction of carbonyl compounds promoted by silicon hydrides under the influence of trimethylsilyl-based reagent"
Aizpurua.MJ, et al.
Canadian Journal of Chemistry, 64(12), 2342-2347 (1986)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service