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389412

Sigma-Aldrich

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
Beilstein:
108550
EC Number:
213-226-1
MDL number:
MFCD00005508
UNSPSC Code:
12352100
PubChem Substance ID:
24864283
NACRES:
NA.22

Assay

97%

form

powder

mp

94-96 °C (lit.)

SMILES string

CN1C(=O)C=CC1=O

InChI

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

InChI key

SEEYREPSKCQBBF-UHFFFAOYSA-N

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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

Signal Word

Danger

Hazard Statements

H302,H314,H317

Hazard Classifications

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

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
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)
Eun Jo Du et al.
PLoS genetics, 12(1), e1005773-e1005773 (2016-01-05)
Pathogen expulsion from the gut is an important defense strategy against infection, but little is known about how interaction between the intestinal microbiome and host immunity modulates defecation. In Drosophila melanogaster, dual oxidase (Duox) kills pathogenic microbes by generating the
Hui Zhou et al.
The Analyst, 143(10), 2390-2396 (2018-04-27)
Glutathione (GSH) exhibits many cellular functions in human pathologies. A sensitive and simple method capable of assaying GSH would be useful to understand the mechanism of GSH-related diseases. In this study, a new colorimetric and fluorescent off-on probe, 3-oxo-3H-phenoxazin-7-ylthiophene-2-carboxylate, is
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