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136727

Sigma-Aldrich

3-Chlorobenzyl bromide

97%

Synonym(s):

α-Bromo-3-chlorotoluene

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About This Item

Linear Formula:
ClC6H4CH2Br
CAS Number:
766-80-3
Molecular Weight:
205.48
Beilstein:
636504
EC Number:
212-171-0
MDL number:
MFCD00000597
UNSPSC Code:
12352100
PubChem Substance ID:
24848293
NACRES:
NA.22

Quality Level

100

Assay

97%

form

liquid

refractive index

n20/D 1.588 (lit.)

bp

109-110 °C/12 mmHg (lit.)

density

1.565 g/mL at 25 °C (lit.)

functional group

bromo
chloro

SMILES string

Clc1cccc(CBr)c1

InChI

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

InChI key

LZIYAIRGDHSVED-UHFFFAOYSA-N

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General description

3-Chlorobenzyl bromide reacts with aminoethanol and NaH to yield aminoethyl 3-chlorobenzyl ether.

Application

3-Chlorobenzyl bromide was used in the synthesis of symmetrical and unsymmetrical benzyl thioethers. It was used as starting reagent during the synthesis of 1-(3-chlorobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole dihydrochloride.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBJ7280
STBJ3493
STBG4279V
STBG2737V
STBG1511V

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Convenient and robust one-pot synthesis of symmetrical and unsymmetrical benzyl thioethers from benzyl halides using thiourea.
Eccles KS, et al.
ARKIVOC (Gainesville, FL, United States), ix, 216-218 (2010)
Selective inactivation of monoamine oxidase B by aminoethyl 3-chlorobenzyl ether.
Ding CZ and Silverman RB.
Bioorganic & Medicinal Chemistry, 3(10), 2077-2078 (1993)
Jason Z Vlahakis et al.
Bioorganic & medicinal chemistry, 21(21), 6788-6795 (2013-09-12)
Several analogs based on the lead structure of 1-(4-chlorobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole (clemizole) were synthesized and evaluated as novel inhibitors of heme oxygenase (HO). Many of the compounds were found to be potent and highly selective for the HO-2 isozyme (constitutive), and had

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