769-53-9

Basic information

• Product Name: N,N,2,4-TETRAMETHYLANILINE
• Synonyms: N,N,2,4-TETRAMETHYLANILINE;2,4,N,N-Tetramethylaniline
• CAS NO: 769-53-9
• Molecular Formula: C₁₀H₁₅N
• Molecular Weight: 149.2328
• Mol File: 769-53-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 223.2°Cat760mmHg
• Flash Point: 89.4°C
• Appearance: /
• Density: 0.932g/cm³
• Vapor Pressure: 0.0973mmHg at 25°C
• Refractive Index: 1.54
• CAS DataBase Reference: N,N,2,4-TETRAMETHYLANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N,2,4-TETRAMETHYLANILINE(769-53-9)
• EPA Substance Registry System: N,N,2,4-TETRAMETHYLANILINE(769-53-9)

Safety Data

• Hazardous Substances Data: 769-53-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H15N/c1-8-5-6-10(11(3)4)9(2)7-8/h5-7H,1-4H3

Upstream product

• 50-00-0 formaldehyd 
• 41825-73-4 2-bromo-4,6-dimethylaniline 
• 64-17-5 ethanol 
• 87066-90-8 2-dimethylamino-5-methyl-benzyl alcohol 
• 773871-29-7 4-dimethylamino-3-methyl-benzyl alcohol 
• 609-72-3 N,N-dimethyl-o-toluidine 
• 67-56-1 methanol 
• 95-68-1 2,4-Xylidine 
• 74-88-4 methyl iodide 
• 124-38-9 carbon dioxide 
• 99-97-8 Dimethyl-p-toluidine 
• 77-78-1 dimethyl sulfate 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 

Downstream Products

• 1250211-41-6 ethyl 2-((2,4-dimethylphenyl)(methyl)amino)acetate 
• 76641-11-7 NN,2,4-tetramethyl-6-nitroaniline 
• 13021-13-1 N,2,4-trimethylaniline 
• 76259-11-5 4-(N,N-dimethylamino)-3-methylbenzyl acetate 
• 76259-12-6 N,N,2,4-tetramethyl-6-acetoxyaniline 
• 51770-93-5 4-hydroxy-2,4-dimethyl-2,5-cyclohexadienone 
• 856351-93-4 2,4,N-trimethyl-N-nitroso-aniline 

Relevant articles and documents

Additive-freeN-methylation of amines with methanol over supported iridium catalyst

An efficient and versatile zinc oxide-supported iridium (Ir/ZnO) catalyst was developed to catalyze the additive-freeN-methylation of amines with methanol. Mechanistic studies suggested that the high catalytic reactivity is rooted in the small sizes (1.4 nm) of Ir nanoparticles and the high ratio (93%) of oxidized iridium species (IrOx, Ir3+and Ir4+) on the catalyst. Moreover, the delicate cooperation between the IrOxand ZnO support also promoted its high reactivity. The selectivity of this catalyticN-methylation was controllable between dimethylation and monomethylation by carefully tuning the catalyst loading and reaction solvent. Specifically, neat methanol with high catalyst loading (2 mol% Ir) favored the formation ofN,N-dimethylated amine, while the mesitylene/methanol mixture with low catalyst loading (0.5 mol% Ir) was prone to producing mono-N-methylated amines. An environmentally benign continuous flow system with a recycled mode was also developed for the efficient production ofN-methylated amines. With optimal flow rates and amine concentrations, a variety ofN-methylamines were produced with good to excellent yields in this Ir/ZnO-based flow system, providing a starting point for the clean and efficient production ofN-methylamines with this cost-effective chemical process.

CO2 as a C1-building block for the catalytic methylation of amines

A novel catalytic reaction has been designed to utilize, for the first time, CO2 as a C1 feedstock in the synthesis of N-methylamines. Simple zinc catalysts, based on commercially available zinc salts and ligands, prove highly efficient in promoting both a 6 electron reduction of carbon dioxide and the formation of a C-N bond, using hydrosilanes and amines.