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maleimide
Sign in to saveAlso known as maleic imide
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 are also 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, or a nucleic acid), a reactive group, or a synthetic polymer such as polyethylene glycol. Hum
Chemical data
- Formula
- C4H3NO2
- Molecular weight
- 97.07 g/mol
- IUPAC name
- pyrrole-2,5-dione
- SMILES
- C1=CC(=O)NC1=O
- InChIKey
- PEEHTFAAVSWFBL-UHFFFAOYSA-N
- XLogP
- -0.3
- Polar surface area
- 46.2 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
16,146 papers- Maleimide structure: a promising scaffold for the development of antimicrobial agents.Journal of Asian natural products research · 2022
- Covalent Modification of Biomolecules through Maleimide-Based Labeling Strategies.Bioconjugate chemistry · 2018
- Maleimide-Decorated PEGylated Mucoadhesive Liposomes for Ocular Drug Delivery.Langmuir : the ACS journal of surfaces and colloids · 2022
- Maleimide-functionalized photochromic spirodihydroindolizines.The Journal of organic chemistry · 2013
- Gelatin maleimide microgels for hematopoietic progenitor cell encapsulation.Journal of biomedical materials research. Part A · 2024
via PubMed
Wikidata facts
- Mass
- 97.016378
Show 5 more facts
- topic's main category
- Category:Maleimides
- chemical formula
- C₄H₃NO₂
- canonical SMILES
- C1=CC(=O)NC1=O
- Commons category
- Maleimides
- melting point
- 92
Sources (2)
via Wikidata · CC0
~6 min read
Encyclopedic overview
7 sectionsContents
- Reactions
- Natural maleimides
- Biotechnology and pharmaceutical applications
- Technological applications
- See also
- References
- External links
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 are also 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, or 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.
==Reactions== Many analogues of maleimide are prepared by treating maleic anhydride with amines followed by dehydration.
Excerpted from Wikipedia’s “maleimide” article, available under the CC BY-SA 4.0 licence.