773263

N-(2-Hydroxyethyl)maleimide

97%

• Synonym(s): 1-(2-Hydroxyethyl)-pyrrole-2,5-dione, 1-(2-Hydroxyethyl)maleimide, N-(Ethanol)maleimide, HEMI
• Empirical Formula (Hill Notation): C₆H₇NO₃
• CAS Number: 1585-90-6
• Molecular Weight: 141.12
• MDL number: MFCD00465266
• UNSPSC Code: 12352111
• PubChem Substance ID: 329767614
• NACRES: NA.22

Properties

• assay: 97%
• form: solid
• reaction suitability: reagent type: cross-linking reagent
• mp: 66-67 °C (lit.); 67-74 °C
• functional group: hydroxyl; maleimide
• storage temp.: 2-8°C
• SMILES string: O=C(N1CCO)C=CC1=O
• InChI: 1S/C6H7NO3/c8-4-3-7-5(9)1-2-6(7)10/h1-2,8H,3-4H2
• InChI key: AXTADRUCVAUCRS-UHFFFAOYSA-N

Description

Application

N-(2-Hydroxyethyl)maleimide can be used:

• In the synthesis of (EFA)-based multifunctional oligoester resins with maleimides as end groups by reacting with 9,10-epoxy-18-hydroxyoctadecanoic acid (EFA) and dimethyl adipate catalyzed by Candida antarctica lipase B (CalB).
• As an initiator in ring-opening polymerization of δ-valerolactone catalyzed by trifluoromethanesulfonimide.
• In one-pot synthesis of bio-based polyurethane-imides by reacting with castor oil, eleostearic acid diethanol amide and isophorone diisocyanate.

N-(2-Hydroxyethyl)maleimide may be used to synthesize [2,2-bis(maleimidoethoxy)-
propane (BMEP)], a protein cross-linking reagent with potential application in constructing immunotoxins. It may also be used in preparing thermoresponsive self-healing polyurethanes with the shape-memory property.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H319
• pcodes: P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable