226351

N-Hydroxymaleimide

97%, for peptide synthesis

• Synonym(s): 1-Hydroxypyrrole-2,5-dione
• Empirical Formula (Hill Notation): C₄H₃NO₃
• CAS Number: 4814-74-8
• Molecular Weight: 113.07
• Beilstein: 1524594
• EC Number: 225-385-4
• MDL number: MFCD00005501
• UNSPSC Code: 12352005
• PubChem Substance ID: 24853562
• NACRES: NA.22

Properties

• product name: N-Hydroxymaleimide, 97%
• Quality Level: 200
• Assay: 97%
• form: solid
• reaction suitability: reaction type: Addition Reactions
• mp: 130-133 °C (dec.) (lit.)
• application(s): peptide synthesis
• SMILES string: ON1C(=O)C=CC1=O
• InChI: 1S/C4H3NO3/c6-3-1-2-4(7)5(3)8/h1-2,8H
• InChI key: BUXKULRFRATXSI-UHFFFAOYSA-N

Description

General description

N-Hydroxymaleimide (NHMI) is an organic compound that is widely used as an oxidizing agent in organic synthesis. It is frequently used to selectively oxidize thiols to disulfides and in the synthesis of α, β-unsaturated carbonyl compounds. It can also act as a Michael acceptor and is used in the synthesis of peptides and proteins.

Application

N-Hydroxymaleimide can be used as an oxidant to generate N-hydroxy anilines in situ, which serve as key intermediates in the selective coupling reaction of N-substituted anilines with hydroxylamine derivatives, for the efficient synthesis of aromatic oximes.

Safety Information

• Pictograms: GHS05
• Signal Word: Danger
• Hazard Statements: H314
• Precautionary Statements: P260 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P363
• Hazard Classifications: Eye Dam. 1 - Skin Corr. 1B
• 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