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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:
3005-27-4
Molecular Weight:
268.89
MDL number:
MFCD00102284
UNSPSC Code:
12352100
PubChem Substance ID:
24881339
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

Related Categories

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
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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