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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

Signal Word

Warning

Hazard Statements

H319

Precautionary Statements

P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

773263-250MG:
773263-VAR:
773263-1G:
773263-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
BGBC5256V
MKBN2747

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Enzymatic catalysis as a versatile tool for the synthesis of multifunctional, bio-based oligoester resins
Semlitsch S, et al.
Green Chemistry, 18(7), 1923-1929 (2016)
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)
One-pot synthesis of cyclopentadienyl endcapped poly (2-ethyl-2-oxazoline) and subsequent ambient temperature Diels?Alder conjugations.
Glassner M, et al.
Chemical Communications (Cambridge, England), 47(38), 10620-10622 (2011)
New protein crosslinking reagents that are cleaved by mild acid.
Srinivasachar K & Neville Jr DM.
Biochemistry, 28(6), 2501-2509 (1989)
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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