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773263

Sigma-Aldrich

N-(2-Hydroxyethyl)maleimide

97%

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

assay

97%

form

solid

reaction suitability

reagent type: cross-linking reagent

mp

66-67 °C (lit.)
67-74 °C

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.

Packaging

1 g in glass bottle
250 mg in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Eye Irrit. 2

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

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More documents

Quotes and Ordering

One-pot synthesis of polyurethane-imides with tailored performance from castor and tung oil
Feng Y, et al.
Progress in Organic Coatings, 132(17), 62-69 (2019)
Controlled/living ring-opening polymerization of δ-valerolactone using triflylimide as an efficient cationic organocatalyst
Kakuchi R, et al.
Macromolecules, 43(17), 7090-7094 (2010)
New protein crosslinking reagents that are cleaved by mild acid.
Srinivasachar K & Neville Jr DM.
Biochemistry, 28(6), 2501-2509 (1989)
Self?Healing Polyurethanes with Shape Recovery.
Heo Y & Sodano HA.
Advances in Functional Materials, 24(33), 5261-5268 (2014)
Eddie K Hasty et al.
Orthopedics, 40(4), e641-e647 (2017-04-19)
Proximal humerus fractures in the elderly are increasing in frequency as the population ages. The purpose of this study was to investigate surgical and cost trends in the Medicare population. The PearlDiver database was queried using diagnosis codes to identify

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