Bismaleimide
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IUPAC name
Maleimide
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| Other names
2,5-Pyrroledione
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| Identifiers | |
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3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.007.990 |
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PubChem CID
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| Properties | |
| C4H3NO2 | |
| Molar mass | 97.07 g/mol |
| Melting point | 91 to 93 °C (196 to 199 °F; 364 to 366 K) |
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| Hazards | |
| R-phrases (outdated) | R25 R34 R43 |
| S-phrases (outdated) | S26 S36/37/39 S45 |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| 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 small molecule (such as biotin, a fluorescent dye, an oligosaccharide a nucleic acid), a reactive group, or a synthetic 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 thermoset polymer chemistry. Compounds containing a maleimide group linked with another reactive group, such as an activated N-hydroxysuccinimide ester, are called maleimide heterobifunctional reagents (for example, see SMCC reagent).
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