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553603

Sigma-Aldrich

2,3-Dibromomaleimide

97%

Synonym(s):

3,4-Dibromopyrrole-2,5-dione

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About This Item

Empirical Formula (Hill Notation):
C4HBr2NO2
CAS Number:
1122-10-7
Molecular Weight:
254.86
MDL number:
MFCD00185696
UNSPSC Code:
12352100
PubChem Substance ID:
24879339
NACRES:
NA.22

assay

97%

form

solid

mp

228-231 °C (lit.)

SMILES string

BrC1=C(Br)C(=O)NC1=O

InChI

1S/C4HBr2NO2/c5-1-2(6)4(9)7-3(1)8/h(H,7,8,9)

InChI key

BIKSKRPHKQWJCW-UHFFFAOYSA-N

General description

2,3-Dibromomaleimide a cyclic imide, has a dipole moment of 0.30 debye based on ab initio and density functional theory (DFT) calculations.

Application

2,3-Dibromomaleimide may be used in the synthesis of the following:
  • 2-bromo-3-(1H-indol-3-yl)maleimide via reaction with indolyl magnesium bromide in tetrahydrofuran
  • 2-dibromo-3-propylsulfanyl-maleimide via reaction with propanethiol and sodium acetate in methanol

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

hcodes

H314,H317

Hazard Classifications

Skin Corr. 1B - Skin Sens. 1

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’.

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Jordon Sandland et al.
Bioconjugate chemistry, 30(4), 975-993 (2019-02-16)
This Review aims to highlight key aspects of tetrapyrrole-based antibody-drug conjugates (ADCs) and significant developments in the field since 2010. Many new conjugation methods have been developed and employed in the past decade, and associated with this, there has been
A method for preparing water soluble cyclic polymers
Long S, et al.
Reactive functional Polymers, 80, 15-20 (2014)
Strong fluorescence enhancement of 2-bromo-3-(1H-indol-3-yl) maleimide upon coordination to a Lewis-acidic metal complex.
Kaletas BK, et al.
Chemical Communications (Cambridge, England), 7, 776-777 (2002)
Polarizability and first-order hyperpolarizability of cyclic imides.
Asghari-Khiavi M, et al.
Journal of Molecular Structure: THEOCHEM, 910(1), 56-60 (2009)
Ting Bai et al.
Macromolecular bioscience, 20(7), e1900438-e1900438 (2020-05-15)
Targeting the distinct cholesterol metabolism of tumor cells is proposed as a novel way to treat tumors. Blocking acyl-CoA cholesterol acyltransferase-1 (ACAT-1) by the inhibitor avasimible (Ava), which elevates intracellular free cholesterol levels, is shown to effectively induce apoptosis. However

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