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557781

Sigma-Aldrich

N-Benzyl-2,3-dibromomaleimide

97%

Synonym(s):

1-Benzyl-3,4-dibromo-pyrrole-2,5-dione

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About This Item

Empirical Formula (Hill Notation):
C11H7Br2NO2
CAS Number:
91026-00-5
Molecular Weight:
344.99
MDL number:
MFCD03427193
UNSPSC Code:
12352100
PubChem Substance ID:
24879697
NACRES:
NA.22

Assay

97%

form

solid

mp

117-120 °C (lit.)

SMILES string

BrC1=C(Br)C(=O)N(Cc2ccccc2)C1=O

InChI

1S/C11H7Br2NO2/c12-8-9(13)11(16)14(10(8)15)6-7-4-2-1-3-5-7/h1-5H,6H2

InChI key

DZYLZHRCCNTQCS-UHFFFAOYSA-N

Application

N-Benzyl-2,3-dibromomaleimide may be used in the synthesis of the following maleimide-based dyes, which can be employed in fluorescence quenching:
  • 2,3-bis(3-indolyl)-N-benzylmaleimide
  • 2,3-bis(2′-methyl-3-indolyl)-N-benzylmaleimide
  • 2,3-bis(2-pyrrolyl)-N-benzylmaleimide
  • 2-aryl-N-benzyl-3-bromomaleimides via suzuki cross coupling reaction with aryl boronic acid

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H314,H317

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

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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Bifunctional maleimide dyes as selective anion sensors.
Lin Z, et al.
Tetrahedron, 65(27), 5216-5221 (2009)
"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)

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