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187062

Sigma-Aldrich

3-Bromobenzyl bromide

99%

Synonym(s):

α,3-Dibromotoluene

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About This Item

Linear Formula:
BrC6H4CH2Br
CAS Number:
823-78-9
Molecular Weight:
249.93
Beilstein/REAXYS Number:
2078683
EC Number:
212-519-1
MDL number:
MFCD00000176
UNSPSC Code:
12352100
PubChem Substance ID:
24851249
NACRES:
NA.22
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assay

99%

form

solid

mp

39-41 °C (lit.)

functional group

bromo

SMILES string

BrCc1cccc(Br)c1

InChI

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

InChI key

ZPCJPJQUVRIILS-UHFFFAOYSA-N

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General description

3-Bromobenzyl bromide undergoes reduction with diethylzinc in the presence of Pd(PPh3)4 to yield corresponding hydrocarbon[1].

Application

3-Bromobenzyl bromide was used in the synthesis of:
  • 1,7-di(3-bromobenzyl)cyclen[2]
  • substituted 8-arylquinoline, phosphodiesterase 4 (PDE4) inhibitors[3]

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

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000359393
0000359393
0000294702
0000266984
0000184503

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Reduction of benzylic halides with diethylzinc using tetrakis (triphenylphosphine) palladium as catalyst.
Agrios KA and Srebnik M.
The Journal of Organic Chemistry, 58(24), 6908-6910 (1993)
Synthesis of a new family of bi-and polycyclic compounds via Pd-catalyzed amination of 1, 7-di (3-bromobenzyl) cyclen.
Averin AD, et al.
Tetrahedron Letters, 49(24), 3950-3954 (2008)
Dwight Macdonald et al.
Bioorganic & medicinal chemistry letters, 15(23), 5241-5246 (2005-09-20)
The discovery and SAR of a new series of substituted 8-arylquinoline PDE4 inhibitors are herein described. This work has led to the identification of several compounds with excellent in vitro and in vivo profiles, including a good therapeutic window of
William L Scott et al.
Journal of combinatorial chemistry, 11(1), 14-33 (2008-12-25)
Distributed Drug Discovery (D(3)) proposes solving large drug discovery problems by breaking them into smaller units for processing at multiple sites. A key component of the synthetic and computational stages of D(3) is the global rehearsal of prospective reagents and
William L Scott et al.
Journal of combinatorial chemistry, 11(1), 34-43 (2008-12-25)
For the successful implementation of Distributed Drug Discovery (D(3)) (outlined in the accompanying Perspective), students, in the course of their educational laboratories, must be able to reproducibly make new, high quality, molecules with potential for biological activity. This article reports

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