18707-43-2

Basic information

• Product Name: N-Cyclohexyl-N-methylaniline
• Synonyms: N-Cyclohexyl-N-methylaniline
• CAS NO: 18707-43-2
• Molecular Formula: C₁₃H₁₉N
• Molecular Weight: 0
• Mol File: 18707-43-2.mol
• Article Data: 40

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-Cyclohexyl-N-methylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: N-Cyclohexyl-N-methylaniline(18707-43-2)
• EPA Substance Registry System: N-Cyclohexyl-N-methylaniline(18707-43-2)

Safety Data

• Hazardous Substances Data: 18707-43-2(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthesis, p. 116, 1975 DOI: 10.1055/s-1975-23680

Upstream product

• 100-60-7 N-methylcyclohexylamine 
• 108-90-7 chlorobenzene 
• 614-30-2 N-methyl-N-phenyl-benzenemethanamine 
• 64-18-6 formic acid 
• 1821-36-9 N-phenyl-2-cyclohexylamine 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 98-80-6 phenylboronic acid 
• 50-00-0 formaldehyd 
• 108-94-1 cyclohexanone 
• 62-53-3 aniline 
• 626-62-0 Cyclohexyl iodide 
• 100-61-8 N-methylaniline 
• 615-42-9 1,2-Diiodobenzene 
• 93-61-8 N-methyl-N-phenylformamide 

Downstream Products

• 88799-11-5 4-bromo-N-cyclohexyl-N-methylaniline 
• 87725-00-6 2,6-bis(N-methyl-N-cyclohexyl-4'-aminobenzoyl)pyridine 
• 25754-75-0 N-cyclohexyl-N-methyl-2,4-dinitroaniline 

Relevant articles and documents

Visible light-induced N-methyl activation of unsymmetric tertiary amines

In the presence of methylene group, selective N-methyl activation of tertiary amines has been accomplished with the aid of visible light using organic photocatalyst under air. This protocol explores numerous aliphatic and aromatic substituted tetra-hydroquinoline analogues from various tertiary amines and maleimides. Furthermore, this approach was applied to activate the methyl group of N-methyl carbazole to generate the biologically active molecule.

Alcohol promoted N -methylation of anilines with CO2/H2over a cobalt catalyst under mild conditions

N-Methylation of amines with CO2/H2 to N-methylamines over non-noble metal catalysts is very interesting but remains challenging. Herein, we present an alcohol (e.g., ethanol) promoted strategy for the N-methylation of anilines with CO2/H2 with high efficiency under mild conditions (e.g., 125 °C), which is achieved over a cobalt catalytic system composed of Co(OAc)2·4H2O, triphos and Sn(OTf)2. This catalytic system has a broad substrate scope and is tolerant toward a wide range of anilines and N-methyl anilines, and a series of N,N-dimethyl anilines were obtained in high yields. Mechanism investigation indicates that the alcohol solvent shifts the equilibrium of CO2 hydrogenation by forming an alkyl formate, which further reacts with the amine to produce N-formamide, and Sn(OTf)2 promotes the deoxygenative hydrogenation of N-formamides to afford N-methylamines. This is the first example of the N-methylation of amines with CO2/H2 over a cobalt catalytic system, which shows comparable performance to the reported Ru catalysts and may have promising applications.

Air-tolerant direct reductive N-methylation of amines using formic acid via simple inorganic base catalysis

The construction of N-methyl amine moieties is an important reaction that has found numerous applications. Development of new methylation agents that are more environmentally benign than classical agents, such as iodomethane and methyl sulfate, is still highly desirable. Herein, we report a convenient protocol for direct reductive N-methylation of amines using formic acid as the methylation agent via simple inorganic base catalysis. The present protocol operates under transition-metal-free and air-tolerant conditions. Both the catalyst, K2HPO4, and the reductant, polymethylhydrosiloxane (PMHS), are cheap and easily separable from the crude reaction product mixture. Mechanistic investigations suggest that the reaction occur through the formation of an acetal intermediate followed by the C–N bond formation.