Maleimide

Maleimide

Names
IUPAC name Maleimide
Other names 2,5-Pyrroledione
Identifiers
CAS Number	541-59-3
3D model (Jmol)	Interactive image
ChEBI	CHEBI:16072
ChEMBL	ChEMBL387762
ChemSpider	10471
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) Key: PEEHTFAAVSWFBL-UHFFFAOYSA-N 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).
verify (what is  ?)
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.

Organic chemistry

Maleimide and its derivatives are prepared from maleic anhydride by treatment with amines followed by dehydration.^[1] 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.

Natural maleimides

Only a handful of natural maleimides — exemplified by the cytotoxic showdomycin from Streptomyces showdoensis,^[2] and pencolide from Pe. multicolor^[2] — have been reported. Farinomalein was first isolated in 2009 from the entomopathogenic fungus Isaria farinosa (Paecilomyces farinosus) - source H599 (Japan).^[3]

Biotechnology applications

Maleimides linked to polyethylene glycol chains are often used as flexible linking molecules to attach proteins to surfaces. The double bond readily reacts with the thiol group found on cysteine to form a stable carbon-sulfur bond. Attaching the other end of the polyethylene chain to a bead or solid support allows for easy separation of protein from other molecules in solution, provided these molecules do not also possess thiol groups.

Technological applications

Mono- and bismaleimide-based polymers are used for high temperature applications up to 250 °C.^[4] Maleimides linked to rubber chains are often used as flexible linking molecules to reinforce the rubber (tire). The double bond readily reacts with all hydroxy, amine or thiol groups found on the matrix to form a stable carbon-oxygen, carbon-nitrogen, or carbon-sulfur bond, respectively. Lockheed Martin's F-35B (a VSTOL version of this US fighter) is reportedly composed of bismaleimide materials, in addition to the use of advanced carbon fiber composites.^[5]

See also

• N-Methylmaleimide
• Succinimide

References

1. Cava, M. P.; Deana, A. A.; Muth, K.; Mitchell, M. J. (1973). "N-Phenylmaleimide". Org. Synth.; Coll. Vol., 5, p. 944
2. J. H. Birkinshaw, M. G. Kalyanpur and C. E. Stickings. (1963). "Studies on the biochemistry of microorganisms. 113. Pencolide, a nitrogen-containing metabolite of Penicillium multicolor Grigorievna-Manilova and poradievova.". Biochem. J. 86: 237–243.
3. Sastia P. Putri, Hiroshi Kinoshita, Fumio Ihara, Yasuhiro Igarashi and Takuya Nihira. "Farinomalein, a Maleimide-Bearing Compound from the Entomopathogenic Fungus Paecilomyces farinosus", J. Nat. Prod., 2009, 72 (8), pp.1544-1546. doi:10.1021/np9002806
4. Lin, K.-F.; Lin, J.-S.; Cheng, C.-H. (1996). "High temperature resins based on allylamine/bismaleimides". Polymer. 37 (21): 4729–4737. doi:10.1016/S0032-3861(96)00311-4.
5. "Lockheed Martin F-35B Boasts UFO Technology, Fights For Team USA". International Science Time s. August 21, 2013. Retrieved 28 January 2014.

External links

• The MP4 website, Molecule of the Month, December 2004