Maleimide

Maleimide
Names


IUPAC name Maleimide
Other names 2,5-Pyrroledione
Identifiers
CAS Number	541-59-3^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:16072^N
ChEMBL	ChEMBL387762^Y
ChemSpider	10471^Y
ECHA InfoCard	100.007.990
PubChem	10935
InChI InChI=1S/C4H3NO2/c6-3-1-2-4(7)5-3/h1-2H,(H,5,6,7)^Y Key: PEEHTFAAVSWFBL-UHFFFAOYSA-N^Y InChI=1/C4H3NO2/c6-3-1-2-4(7)5-3/h1-2H,(H,5,6,7) Key: PEEHTFAAVSWFBL-UHFFFAOYAL
SMILES C1=CC(=O)NC1=O
Properties
Chemical formula	C₄H₃NO₂
Molar mass	97.07 g/mol
Melting point	91 to 93 °C (196 to 199 °F; 364 to 366 K)
Solubility in water	organic solvents
Hazards
R-phrases	R25 R34 R43
S-phrases	S26 S36/37/39 S45
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N (what is ^YN ?)
Infobox references

Maleimide is a chemical compound with the formula H₂C₂(CO)₂NH (see diagram). This unsaturated imide is an important building block in organic synthesis. The name is a contraction of maleic acid and imide, the -C(O)NHC(O)- functional group. Maleimides also describes a class of derivatives of the parent maleimide where the NH group is replaced with alkyl or aryl groups such as a methyl or phenyl, respectively. The substituent can also be a polymer such as polyethylene glycol. Human hemoglobin chemically modified with maleimide-polyethylene glycol is a blood substitute called MP4.

Maleimide and its derivatives are prepared from maleic anhydride by treatment with amines followed by dehydration. A special feature of the reactivity of maleimides is their susceptibility to additions across the double bond either by Michael additions or via Diels-Alder reactions. Bismaleimides are a class of compounds with two maleimide groups connected by the nitrogen atoms via a linker, and are used as crosslinking reagents in polymer chemistry.

Only a handful of natural maleimides — exemplified by the cytotoxic showdomycin from Streptomyces showdoensis, and pencolide from Pe. multicolor — have been reported. Farinomalein was first isolated in 2009 from the entomopathogenic fungus Isaria farinosa (Paecilomyces farinosus) - source H599 (Japan).

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