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381543

Sigma-Aldrich

N-Cyclohexylmaleimide

97%

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About This Item

Formule empirique (notation de Hill):
C10H13NO2
Numéro CAS:
1631-25-0
Poids moléculaire :
179.22
Numéro CE :
216-630-6
Numéro MDL:
MFCD00043904
Code UNSPSC :
12352100
ID de substance PubChem :
24863825
Nomenclature NACRES :
NA.22

Pureté

97%

Pf

89-91 °C (lit.)

Chaîne SMILES 

O=C1C=CC(=O)N1C2CCCCC2

InChI

1S/C10H13NO2/c12-9-6-7-10(13)11(9)8-4-2-1-3-5-8/h6-8H,1-5H2

Clé InChI

BQTPKSBXMONSJI-UHFFFAOYSA-N

Description générale

N-Cyclohexylmaleimide (CHMI, NCMI) is a cyclic imide. Diels-Alder reactions of 9-hydroxymethylanthracene with CHMI catalyzed by hydrophobic nanospace confined within the self-assembled Pd6 open cage bearing triimidazole walls have been reported. It undergoes Diels-Alder reactions with various aromatic hydrocarbons promoted by self-assembled coordination cage. This cage acts as nanometer-sized molecular flask and hence promotes this reaction. CHMI is reported to undergo radical polymerization readily under various polymerization conditions to afford poly(CHMI), having excellent thermal stability.

Application

N-Cyclohexylmaleimide (CHMI, NCMI) may be used for the preparation of hyperbranched copolymers of p-(chloromethyl)styrene (CMS) and NCMI, via atom transfer radical copolymerization reaction.
N-Cyclohexylmaleimide contaminated with N-cyclohexylmaleamic acid (less than 0.9 wt%) may be used for the heat-resistant poly(methyl methacrylate) resin free from coloration and for methyl methacrylate homopolymer. It may be used as monomer in the preparation of styrene/N-cyclohexylmaleimide copolymers with small polydispersities and controlled molecular weights, via free radical copolymerization. It may be used in the synthesis of hyperbranched copolymers by the atom transfer radical copolymerization with p-(chloromethyl)styrene catalyzed by CuCl/2,2′-bipyridine in cyclohexanone or anisole.

Pictogrammes

Skull and crossbonesEnvironment
GHS06,GHS09

Mention d'avertissement

Danger

Classification des risques

Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 3 - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1A - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Bingchuan Wei et al.
Journal of chromatography. A, 1526, 104-111 (2017-10-29)
Reversed-phase liquid chromatography (RPLC) has been commonly used in IgG2 disulfide isoforms analysis. Recently, the columns packed with large pore superficially porous particles (SPP) have become available commercially. This work explores the application of this SPP technology in IgG2 disulfide
Synthesis of N-cyclohexylmaleimide for heat-resistant transparent methacrylic resin.
Kita Y, et al.
Journal of Applied Polymer Science, 63(3), 363-368 (1997)
Increase in thermal stability of vinyl polymers through radical copolymerization with N-cyclohexylmaleimide.
Otsu T, et al.
Polymer International, 25(3), 179-184 (1991)
Living free radical donor-acceptor copolymerization of styrene and N-cyclohexylmaleimide and the synthesis of poly [styrene-co-(N-cyclohexylmaleimide)]/polystyrene block copolymers.
Schmidt-Naake G and Butz S.
Macromolecular Rapid Communications, 17(9), 661-665 (1996)
Shinnosuke Horiuchi et al.
Chemistry, an Asian journal, 6(7), 1839-1847 (2011-02-22)
A self-assembled coordination cage serves as a nanometer-sized molecular flask to promote the Diels-Alder reactions of aromatic hydrocarbons with N-cyclohexylmaleimide. The coordination cage accelerated the Diels-Alder reaction of anthracene at the electronically unfavorable, terminal benzene ring to give a compact
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