Skip to Content
Merck

553603

Sigma-Aldrich

2,3-Dibromomaleimide

97%

Synonym(s):

3,4-Dibromopyrrole-2,5-dione

Sign Into View Organizational & Contract Pricing

Select a Size


Select a Size

Change View

About This Item

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

Assay

97%

form

solid

mp

228-231 °C (lit.)

functional group

bromo
maleimide

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.[1]

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]
  • 2-dibromo-3-propylsulfanyl-maleimide via reaction with propanethiol and sodium acetate in methanol[3]

Pictograms

CorrosionExclamation mark

Signal Word

Danger

Hazard Statements

Hazard Classifications

Skin Corr. 1B - Skin Sens. 1

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
A method for preparing water soluble cyclic polymers
Long S, et al.
Reactive functional Polymers, 80, 15-20 (2014)
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
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
Polarizability and first-order hyperpolarizability of cyclic imides.
Asghari-Khiavi M, et al.
Journal of Molecular Structure: THEOCHEM, 910(1), 56-60 (2009)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service