53477-27-3

Usage

InChI:InChI=1/C16H20N2/c1-17-15-8-4-13(5-9-15)12-14-6-10-16(11-7-14)18(2)3/h4-11,17H,12H2,1-3H3

Upstream product

• 100-61-8 N-methylaniline 
• 98-10-2 benzenesulfonamide 
• 121-69-7 N,N-dimethyl-aniline 
• 101-77-9 4,4'-diamino diphenyl methane 
• 616-38-6 carbonic acid dimethyl ester 
• 60565-88-0 bis(4-methylphenyl)iodonium hexafluorophosphate 
• 70458-22-9 3-chlorobenzoic 2-cyclopropylacetic peroxyanhydride 
• 1564-64-3 9-Bromoanthracene 
• 56-23-5 tetrachloromethane 
• 127598-85-0 N-(4’-(N’,N’-dimethylamino)benzyl)-4-methylaniline 

Downstream Products

• 101-61-1 4,4'-methylene-bis(N,N-dimethylaniline) 

Relevant academic research and scientific papers

Full N,N-Methylation of 4,4′-Methylenedianiline with Dimethyl Carbonate: A Feasible Access to 4,4′-Methylene bis(N,N-Dimethylaniline)

The full N,N-methylation of 4,4′-methylenedianiline (MDA) with dimethyl carbonate (DMC) was investigated. The yield of the major product 4,4′-methylene bis(N,N-dimethylaniline) (MBDMA) reached as high as 97% over NaY catalyst at 190°C for 6 h. The catalyst could be used for two more times with acceptable MBDMA yields higher than 90%. The main by-products were identified as three N-methylated derivatives. Surprisingly, the formation of the N-methoxycarbonylation product was extremely restrained, which could be produced in high yields of 98% on zinc acetate catalyst. Furthermore, the reaction pathway to the major product MBDMA was proposed. Finally, a feasible synthetic route of 4,4′-methylene bis(N,N-dimethylaniline) (MBDMA) was established, featuring a high yield, mild reaction conditions, and simple operations.

Substituted tetraphenyl porphyrin catalyzed oxidative N-dealkylation of tertiary amine using molecular oxygen

Oxidative N-dealkylation of NN-dimethylaniline catalyzed by substituted tetraaryl porphyrin complexes of iron and manganese with molecular oxygen, gave a mixture of dealkylated, monooxygenated and dimerised compounds as products. Presence of substituents on the catalyst effects nature and yield of products formed. One electron transfer route [E T) predominated over H-atom abstraction [HAT] in most of the reactions.

Unexpected C=N bond formation via NaI-catalyzed oxidative de-tetra-hydrogenative cross-couplings between N,N-dimethyl aniline and sulfamides

A direct and convenient C=N bond formation reaction was reported, which was a de-tetra-hydrogenative cross-coupling (DTCC) reaction between N,N-dimethyl aniline and sulfamide under transition-metal-free conditions, and to give sulfonyl amidine derivatives in moderate to high yields.

Photochemical Reaction of Diaryliodonium Salts with Dimethylaniline

A solution of 4,4'-dimethyldiphenyl iodonium tettrafluoroborate and N,N-dimethylaniline in acetonitrile is irradiated by UV light to give iodotoluene, toluene, 4,4'-methylenebis(N,N-dimethylaniline), crystal violet, methyl violet. KEY WORDS: 4,4'-dimethyldiuphenyl iodonium salt; N,N-dimethylaniline; 4,4'-methylenebis(N,N-dimethylaniline); crystal violet; methyl violet.

AROMATIC TERTIARY AMINES AND n-BUTYL NITRITE

The reaction between alkyl nitrites, particularly n-butyl nitrite, and tertiary aromatic amines under a variety of experimental conditions promptly yielded products of N-dealkylation-N-nitrosation, ring nitration, ipso-substitution and, occasionally, combinations of these processes.Aminoethers were detected as final products and intermediates on the way to N-nitrosations.Reaction pathways are suggested for some of the observed behaviours on the basis of experimental evidences whereas other alternatives are discarded.

Amine-Induced Reactions of Diacyl Peroxides

The decompositions of 3-chlorobenzoyl cyclobutylformyl peroxide (3a), and 3-chlorobenzoyl cyclopropylacetyl peroxide (3b) induced by 1-azabicyclooctane (Q), N1,N1,N4,N4-tetramethyl-1,4-benzenediamine (W), 1,4-diazabicyclooctane (DABCO), and N,N-dimethylaniline (DMA) were investigated.Peroxides 3 were selected for study because distinctive product patterns were expected from decompositions induced by the alternative SN2 and SET pathways.Q and W were selected as amines likely to react by the SN2 and SET pathways, respectively.Q reacted with3 to give products characteristic of the intermediacy of an ion pair (general structure: R3NOCOC4H7+ArCO2-) formed by the SN2 pathway, while W reacted with 3 to give rapid formation of the C4H7CO2 radical, indicative of an SET pathway.Based on the results with Q and W, we interpret the results with DABCO and DMA to indicate that both induce the decomposition of 3 by the SN2 pathway.Thus, peroxides 3 have been shown to be structurally sensitive to the modes of their induced decomposition, and are, potentially, mechanistic probes for ascertaining the mechanism of induced peroxide decomposition by closed-shell molecules.

Photochemical Reactions of Bromoanthracenes with N,N-Dimethylaniline in Solution

Major products of the photolysis of 9-bromoanthracene and 9,10-dibromoanthracene in benzene and acetonitrile as well as photochemical reaction products of the two bromoanthracenes with N,N-dimethylaniline in these solvents have been isolated and identified.The mechanisms of partial reactions are discussed and attention is paid to the medium effect on the photochemical transformations. - Keywords: Photochemical Reactions, Bromoanthracenes