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595934

Sigma-Aldrich

2,3-Dibromo-N-methylmaleimide

99%

Synonym(s):

1-Methyl-3,4-dibromomaleimide, 3,4-Dibromo-1-methyl-1H-pyrrole-2,5-dione, 3,4-Dibromo-1-methyl-2,5-dihydropyrrole-2,5-dione, 3,4-Dibromo-1-methylpyrrole-2,5-dione, 3,4-Dibromo-N-methylmaleimide, 3,4-Dibromo-N-methylpyrrole-2,5-dione, N-Methyl-2,3-dibromomaleimide, N-Methyldibromomaleimide

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About This Item

Empirical Formula (Hill Notation):
C5H3Br2NO2
CAS Number:
Molecular Weight:
268.89
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

99%

mp

120-124 °C (lit.)

SMILES string

CN1C(=O)C(Br)=C(Br)C1=O

InChI

1S/C5H3Br2NO2/c1-8-4(9)2(6)3(7)5(8)10/h1H3

InChI key

CKITYUQKOJMMOI-UHFFFAOYSA-N

Application

2,3-Dibromo-N-methylmaleimide can be used to synthesize bis-indolylmaleimides via reaction with indolyl magnesium bromide. It can also undergo mono-cross coupling with triorganoindium derivatives which can be further coupled with naphthodithiophene to form an intermediate for [5]thiahelicene synthesis.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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"Metal-catalyzed cross-coupling reactions of halomaleic anhydrides and halomaleimides: synthesis of structurally interesting and biologically important natural and unnatural products"
Deore SP and Argade PN
Synthesis, 46(03), 281-289 (2014)
Synthesis of arcyriarubin B and related bisindolylmaleimides.
Brenner M, et al.
Tetrahedron, 44(10), 2887-2892 (1988)

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