876-00-6

Upstream product

• 698-69-1 4-chloro-N,N-dimethylaniline 

Downstream Products

• 10219-10-0 N-(4-chloro-phenyl)-N-methylacetamide 
• 57649-14-6 5-chloro-2-(N,N-dimethylamino)phenol 
• 1616786-36-7 5-chloro-2-(N,N-dimethylamino)phenyl trifluoromethanesulfonate 
• 1616786-51-6 ethyl (5-chloro-2-(N,N-dimethylamino)phenyl)acetate 
• 36256-04-9 4-chloro-2-bromo-N,N-dimethylaniline 
• 698-69-1 4-chloro-N,N-dimethylaniline 
• 932-96-7 N-methyl(p-chloroaniline) 

Relevant academic research and scientific papers

Renewable waste rice husk grafted oxo-vanadium catalyst for oxidation of tertiary amines to N-oxides

Low cost renewable waste rice husks (RH) have been used as a support for grafting of an oxo-vanadium Schiff base via covalent attachment for the oxidation of tertiary amines to N-oxide. The synthesis of the desired RH grafted oxo-vanadium complex involves prior functionalization of the RH support with amino-propyltrimethoxysilane (APTMS) followed by its reaction with salicylaldehyde to get an RH-functionalized Schiff base which subsequently reacted with vanadyl sulphate to get the targeted oxo-vanadium catalyst. The synthesized catalyst was found to be an efficient heterogeneous catalyst and afforded an excellent yield of corresponding N-oxides via oxidation of tertiary amines with hydrogen peroxide as an oxidant. Furthermore, the synthesized catalyst was found to be quite stable and showed consistent activity for five runs without any loss in activity.

Metal-free functionalization of N, N-dialkylanilines via temporary oxidation to N, N-dialkylaniline N-oxides and group transfer

A simple set of protocols for the controlled elaboration of anilines is reported allowing access to a diverse array of aminophenols, aminoarylsulfonates, alkylated anilines, and aminoanilines in 29-95% yield in a single laboratory operation from easily isolable, bench-stable N,N-dialkylaniline N-oxides. The introduction of new C-O, C-C, and C-N bonds on the aromatic ring is made possible by a temporary increase in oxidation level and excision of a weak N-O bond.

Mechanism of the dimethyldioxirane oxidation of N,N-dimethylanilines

Relative rates of dimethyldioxirane oxidation of a number of para-substituted N,N-dimethylanilines in acetone at 5°C are compared with those of reactions with methyl iodide and other oxidants. The reactions with dimethyldioxirane followed the Hammett relationship with a ρ value of -1.0. Measurement of the second order rate constants for the dimethyldioxirane reactions in aqueous acetonitrile containing potassium nitrate at 21°C, showed better correlation with the Hammett relationship (ρ = 0.89) than with the Okamoto-Brown model (ρ+ = 0.56). The reaction rates are accelerated greatly in the presence of water such that the respective pseudo first order rate constants for the oxidation of N,N-dimethyl-4-nitroaniline in acetone and water are 6.3 × 10-3 and 5.86 s-1, respectively. All of the data are consistent with a concerted electrophilic mechanism and there is no evidence of free radical or electron transfer reactions.

OXIDATION OF AMINES WITH 4a-FlEt-OOH: AN ENZYME MODEL OF FAD-CONTAINING MONOOXYGENASE

Unlike the real enzyme, FAD-containing monooxygenase, 4a-FlEt-OOH, oxidizes most of common primary, secondary and tertiary water-soluble amines, such as N-methylmorpholine and n-octylamine.Both kinetic rates and products of the oxidation were obtained.The plots of rates vs. pKa values gave three different correlations lines depending upon the types of amines.

THE MECHANISTIC MODE OF OXIDATION OF SUBSTITUTED N,N-DIMETHYLANILINES, THIOANISOLES, AND METHYL PHENYL SULFOXIDES BY 5-ETHYL-4a-HYDROPEROXY-3-METHYL-LUMIFLAVIN (4a-FlEt-OOH)

In the oxidation of the title compounds, 5-ethyl-4a-hydroperoxy-3-methyl-lumiflavin (4a-FlEt-OOH), was found to be an electrophilic oxidant similar to m-chloroperoxybenzoic acid.However, the stereoselectivity of the oxidation of cyclic sulfides to the corresponding sulfoxides by 4a-FlEt-OOH was less pronounced than that of the oxygenation with flavin-containing monooxygenase.