769-53-9

Usage

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

Upstream product

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

Downstream Products

• 51770-93-5 4-hydroxy-2,4-dimethyl-2,5-cyclohexadienone 
• 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 
• 76641-11-7 NN,2,4-tetramethyl-6-nitroaniline 
• 1250211-41-6 ethyl 2-((2,4-dimethylphenyl)(methyl)amino)acetate 
• 856351-93-4 2,4,N-trimethyl-N-nitroso-aniline 

Relevant academic research and scientific papers

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.

Reductive amination of tertiary anilines and aldehydes

An unprecedented oxidant-mediated reductive amination of tertiary anilines and aldehydes without external reducing agents was developed via the nucleophilic attack of the oxygen atom of the carbonyl group to in situ generated iminium ions, in which tertiary anilines were used as both nitrogen source and reducing agent for the first time. The Royal Society of Chemistry 2013.