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427691

Sigma-Aldrich

3-Iodobenzyl bromide

95%

Synonym(s):

α-Bromo-m-iodotoluene, 1-(Bromomethyl)-3-iodobenzene, 3-(Bromomethyl)iodobenzene, m-Iodobenzylbromide

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About This Item

Linear Formula:
IC6H4CH2Br
CAS Number:
49617-83-6
Molecular Weight:
296.93
MDL number:
MFCD00019016
UNSPSC Code:
12352100
PubChem Substance ID:
24866775
NACRES:
NA.22

assay

95%

mp

46-51 °C (lit.)

SMILES string

BrCc1cccc(I)c1

InChI

1S/C7H6BrI/c8-5-6-2-1-3-7(9)4-6/h1-4H,5H2

InChI key

BACZSVQZBSCWIG-UHFFFAOYSA-N

Related Categories

General description

3-Iodobenzyl bromide (3-IBBr, m-iodobenzyl bromide) is a meta-isomer of iodobenzyl bromide. It can be synthesized by the bromination of m-iodotoluene.

Application

3-Iodobenzyl bromide (3-IBBr, m-iodobenzyl bromide) was used as a derivatization reagent for the extraction and purification of thiouracil (TU).
It may be used in the synthesis of the following:
  • meta-substituted phenylalanine derivatives
  • N6-substituted aristeromycin derivative
  • (N)-methanocarba-N6-(3-iodobenzyl)adenosine

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)

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’.

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Reaction of some sulfonyl halides with trypsin.
Kuranova IP and Konareva NV.
Bulletin of the Academy of Sciences of the USSR, Division of chemical science, 22(10), 2251-2254 (1973)
Julie A L Kiebooms et al.
Applied and environmental microbiology, 80(23), 7433-7442 (2014-09-28)
In recent years, the frequent detection of the banned thyreostat thiouracil (TU) in livestock urine has been related to endogenous TU formation following digestion of glucosinolate-rich Brassicaceae crops. Recently, it was demonstrated that, upon in vitro digestion of Brassicaceae, fecal
Phase Transfer Catalyst (PTC) Catalyzed Alkylations of Glycinamides for Asymmetric Syntheses of alpha-Amino Acid Derivatives.
Park YS, et al.
Bull. Korean Chem. Soc., 22(9), 958-962 (2001)
K A Jacobson et al.
Journal of medicinal chemistry, 43(11), 2196-2203 (2000-06-08)
Adenosine receptor agonists have cardioprotective, cerebroprotective, and antiinflammatory properties. We report that a carbocyclic modification of the ribose moiety incorporating ring constraints is a general approach for the design of A(1) and A(3) receptor agonists having favorable pharmacodynamic properties. While
Barbara Woźniak et al.
Journal of veterinary research, 62(4), 511-517 (2019-02-08)
In the European Union, the use of thyreostatic drugs for fattening slaughter animals has been banned since 1981 under Council Directive 81/602/EEC. For protection of consumer health against unwanted residues and in compliance with Directive 96/23, each EU country must

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