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773263

Sigma-Aldrich

N-(2-Hydroxyethyl)maleimide

97%

Synonym(s):

1-(2-Hydroxyethyl)-pyrrole-2,5-dione, 1-(2-Hydroxyethyl)maleimide, N-(Ethanol)maleimide, HEMI

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About This Item

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

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

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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.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H319

Hazard Classifications

Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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