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Merck
CN

773263

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
NACRES:
NA.22
PubChem Substance ID:
329767614
UNSPSC Code:
12352111
MDL number:
MFCD00465266

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Product Name

N-(2-Hydroxyethyl)maleimide, 97%

InChI

1S/C6H7NO3/c8-4-3-7-5(9)1-2-6(7)10/h1-2,8H,3-4H2

SMILES string

O=C(N1CCO)C=CC1=O

InChI key

AXTADRUCVAUCRS-UHFFFAOYSA-N

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

Quality Level

200

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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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000363968
0000363969
0000363968
0000363969
0000232146

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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)
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)
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)
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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