1631-25-0

Basic information

• Product Name: N-Cyclohexylmaleimide
• Synonyms: N-CYCLOHEXYLMALEIC IMIDE;N-CYCLOHEXYLMALEIMIDE;TIMTEC-BB SBB005910;ASISCHEM D13289;1-CYCLOHEXYL-PYRROLE-2,5-DIONE;1-CYCLOHEXYL-1H-PYRROLE-2,5-DIONE;AKOS MSC-0038;N-Cyclohexylmaleinimide
• CAS NO: 1631-25-0
• Molecular Formula: C₁₀H₁₃NO₂
• Molecular Weight: 179.22
• EINECS: 216-630-6
• Product Categories: Intermediates of Dyes and Pigments;N-Substituted Maleimides;N-Substituted Maleimides, Succinimides & Phthalimides;Carbonyl Compounds;Cyclic Imides;Organic Building Blocks
• Mol File: 1631-25-0.mol
• Article Data: 32

Chemical Properties

• Melting Point: 89-91 °C(lit.)
• Boiling Point: 132 °C / 17mmHg
• Flash Point: 130.6 °C
• Appearance: /
• Density: 1.226 g/cm³
• Vapor Pressure: 0.00132mmHg at 25°C
• Refractive Index: 1.564
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Insoluble in water
• PKA: -2.26±0.20(Predicted)
• Water Solubility: 260mg/L at 25℃
• CAS DataBase Reference: N-Cyclohexylmaleimide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Cyclohexylmaleimide(1631-25-0)
• EPA Substance Registry System: N-Cyclohexylmaleimide(1631-25-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• RIDADR: 2811
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 1631-25-0(Hazardous Substances Data)

Usage

Description

N-Cyclohexylmaleimide (CHMI, NCMI) is a cyclic imide that readily undergoes radical polymerization to form poly(CHMI) with excellent thermal stability. It is also known for its participation in Diels-Alder reactions with various aromatic hydrocarbons, which are promoted by self-assembled coordination cages acting as nanometer-sized molecular flasks.

Uses

Used in Polymer Synthesis:
N-Cyclohexylmaleimide is used as a monomer for the preparation of hyperbranched copolymers of p-(chloromethyl)styrene (CMS) and NCMI via atom transfer radical copolymerization reaction. This application takes advantage of its ability to readily undergo radical polymerization, resulting in copolymers with unique properties.
Used in Organic Chemistry:
In the field of organic chemistry, N-Cyclohexylmaleimide is used as a reactant in Diels-Alder reactions with 9-hydroxymethylanthracene, catalyzed by hydrophobic nanospace confined within self-assembled Pd6 open cages bearing triimidazole walls. This application showcases its utility in facilitating specific chemical reactions and the formation of complex molecular structures.

Synthesis Reference(s)

Synthetic Communications, 20, p. 1607, 1990 DOI: 10.1080/00397919008053079

Flammability and Explosibility

Notclassified

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

Upstream product

• 21477-59-8 (Z)-3-(cyclohexylcarbamoyl)acrylic acid 
• 108-31-6 maleic anhydride 
• 108-91-8 cyclohexylamine 
• 31930-36-6 ethyl (Z)-3-iodopropenoate 
• 3173-53-3 Cyclohexyl isocyanate 
• 1314-23-4 zirconium(IV) oxide 
• 7631-86-9 SiO₂ 
• 109-73-9 N-butylamine 
• 541-59-3 maleiimide 
• 108-93-0 cyclohexanol 
• 24564-83-8 C₁₀H₁₅NO₃ 

Downstream Products

• 134220-50-1 (4aS,5aS,8aR,8bS)-2-[Bis-(1-cyclohexyl-2,5-dioxo-pyrrolidin-3-yl)-methyl]-7-cyclohexyl-3-methyl-4a,5a,8a,8b-tetrahydro-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8-dione 
• 92176-79-9 3-(3,5-di-t-butyl-4-hydroxyphenylthio)-1-cyclohexylpyrrolidine-2,5-dione 
• 111363-51-0 N-cyclohexyl-3-<(N,N-dibenzylamino)oxy>pyrrolidine-2,5-dione 
• 73565-25-0 1-cyclohexyl-5-cyclohexylaminotetrazole 
• 6301-71-9 1-cyclohexyl-2,5-pyrrolidinedione 
• 898263-00-8 (1R,3S,3aR,6aS)-1-Benzyl-3-(4-chloro-phenyl)-5-cyclohexyl-4,6-dioxo-octahydro-pyrrolo[3,4-c]pyrrole-1-carboxylic acid 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-undecyl ester 
• 139477-41-1 (S)-1-Cyclohexyl-3-phenyl-pyrrolidine-2,5-dione 
• 139477-41-1 (R)-1-cyclohexyl-3-phenyl-2,5-pyrrolidinedione 

Relevant articles and documents

An improved approach to n-substituted maleimides and phthalimides by microwave-promoted mttsunobu reaction

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Dual organic dyes as a pseudo-redox mediation system to promotion of tandem oxidation /[3+2] cycloaddition reactions under visible light

An atom- and step-economy protocol has been developed to synthesize some new biologically active pyrrolo[2,1-a]isoquinoline alkaloids via redox mediation system under visible light irradiation. A vast variety of double and triple bonds, as dipolarophiles, treated with in situ generated azomethine ylides to prepare corresponding products in good to excellent yields. This metal-free method effectively promoted oxidation/[3 + 2] cycloaddition/oxidative/aromatization domino reaction without further oxidant using dual organic dyes as pseudo-redox mediation system. Besides, for most of the products, product precipitate was readily separated from reaction media. To the best of our knowledge, this is the first report of dual dyes as a pseudo-redox mediation system.

Regioselective hydroarylation and arylation of maleimides with indazoles: Via a Rh(iii)-catalyzed C-H activation

Switchable Rh(iii)-catalyzed highly regioselective hydroarylation and oxidative arylation of maleimides with 2-arylindazoles via C-H activation have been demonstrated. The reaction affords 3-(2-(2H-indazol-2-yl)phenyl)succinimide and 3-(2-(2H-indazol-2-yl)phenyl)maleimide derivatives in high yields with wide functional group tolerance. A mechanistic study was performed to depict C-H bond cleavage that might be involved in the turnover limiting step.