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558958

Sigma-Aldrich

4-Chlorobenzyl bromide

97%

Synonym(s):

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

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$391.00
100 G
$892.00

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25 G
$391.00
100 G
$892.00

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

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Quality Level

200

assay

97%

form

solid

mp

48-52 °C (lit.)

functional group

bromo
chloro

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.[1] It can be synthesized by reacting 4-chlorobenzyl alcohol with bromodimethylsulfonium bromide (BDMS)[2] It can also be synthesized by refluxing a mixture of 4-chlorobenzaldehyde, chlorotrimethylsilane, 1,1,3,3-tetramethyldisiloxane and lithium bromide.[3]

Application

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

Packaging

4-Chlorobenzyl bromide may be used to synthesize:
  • 1-[1-[2-[(4-chlorobenzyl)thio]phenyl]vinyl]-1H-imidazole[5]
  • 6-[4-(4-chlorobenzyl)piperazinyl]chromane[6]
  • N,N′-bis(4-chlorobenzyl)piperazine[7]
  • N-(4-chlorobenzyl)piperazine[7]

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL4281
BCCH4241
BCCJ5952
BCCJ5951
BCCC8006

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Gazi S and Ananthakrishnan R
Royal Society of Chemistry Advances, 2(20), 7781- 7787 (2012)
6-(4-Benzylpiperazin-1-yl) benzodioxanes as selective ligands at cloned primate dopamine D 4 receptors.
Hodgetts KJ, et al.
Bioorganic & Medicinal Chemistry, 9(12), 3207-3213 (2001)
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)
Synthesis and antifungal activity of new 1-vinylimidazoles.
Ogata M, et al.
Journal of Medicinal Chemistry, 30(8), 1348-1354 (1987)
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