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Merck

389412

N-Methylmaleimide

97%

Synonym(s):

1-Methyl-1H-pyrrole-2,5-dione, 1-Methyl-2,5-dihydro-1H-pyrrole-2,5-dione, 1-Methylpyrrole-2,5-dione, N-Methyl maleic imide, N-Methylpyrrole-2,5-dione

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About This Item

Empirical Formula (Hill Notation):
C5H5NO2
CAS Number:
930-88-1
Molecular Weight:
111.10
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24864283
EC Number:
213-226-1
Beilstein/REAXYS Number:
108550
MDL number:
MFCD00005508
Assay:
97%
Form:
powder

Key Documents

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InChI key

SEEYREPSKCQBBF-UHFFFAOYSA-N

InChI

1S/C5H5NO2/c1-6-4(7)2-3-5(6)8/h2-3H,1H3

SMILES string

CN1C(=O)C=CC1=O

assay

97%

form

powder

Quality Level

200

functional group

imide, maleimide

Related Categories

Application

N-Methylmaleimide can be used:
  • In the synthesis of organic structure directing agents for designing silicogermanate zeolites.
  • As a dienophile in Diels-Alder reaction.
  • For the synthesis of biologically active pyrrolo[2,1-a]isoquinolines.
  • As a dipolarophile in [3 + 2] dipolar addition reactions.
  • As a co-monomer in atom transfer radical polymerization of styrene to obtain styrene copolymers with programmed microstructure.

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Skin Corr. 1B - Skin Sens. 1

Storage Class

8A - Combustible corrosive hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ9346
MKCX6813
MKCV7090
MKCX0844
MKCW7173

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Asymmetric organocatalytic three-component 1, 3-dipolar cycloaddition: Control of stereochemistry via a chiral br?nsted acid activated dipole.
Chen XH, et al.
Journal of the American Chemical Society, 130(17), 5652-5653 (2008)
A facile procedure for controlling monomer sequence distribution in radical chain polymerizations.
Pfeifer S and Lutz JF
Journal of the American Chemical Society, 129(31), 9542-9543 (2007)
Visible-light-induced oxidation/[3+ 2] cycloaddition/oxidative aromatization sequence: a photocatalytic strategy to construct pyrrolo [2, 1-a] isoquinolines.
Zou YQ, et al.
Angewandte Chemie (International Edition in English), 50(31), 7171-7175 (2011)
The ITQ-37 mesoporous chiral zeolite.
Sun J, et al.
Nature, 458(7242), 1154-1154 (2009)
Dongfang Xiang et al.
Frontiers in chemistry, 8, 7-7 (2020-02-13)
Hydrogels with photo-responsive mechanical properties have found broad biomedical applications, including delivering bioactive molecules, cell culture, biosensing, and tissue engineering. Here, using a photocleavable protein, PhoCl, as the crosslinker we engineer two types of poly(ethylene glycol) hydrogels whose mechanical stability
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