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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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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)
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)
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)
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