389412

Sigma-Aldrich

N-Methylmaleimide

97%

Empirical Formula (Hill Notation):
C5H5NO2
CAS Number:
Molecular Weight:
111.10
Beilstein/REAXYS Number:
108550
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

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

Looking for similar products? Visit Product Comparison Guide

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.

Packaging

5, 25 g in glass bottle

Pictograms

CorrosionExclamation mark

Signal Word

Danger

Hazard Statements

Precautionary Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 1759 8 / PGII

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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...
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)
The ITQ-37 mesoporous chiral zeolite.
Sun J, et al.
Nature, 458(7242), 1154-1154 (2009)
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)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service

Social Media

LinkedIn icon
Twitter icon
Facebook Icon
Instagram Icon

MilliporeSigma

Research. Development. Production.

We are a leading supplier to the global Life Science industry with solutions and services for research, biotechnology development and production, and pharmaceutical drug therapy development and production.

© 2021 Merck KGaA, Darmstadt, Germany and/or its affiliates. All Rights Reserved.

Reproduction of any materials from the site is strictly forbidden without permission.