7006-52-2

Usage

Uses

Used in Pharmaceutical Industry:
3-CHLORO-N-METHYLANILINE is used as a starting material for the preparation of various pharmaceutical compounds, including:
1. 2N-(2-bromoethyl)-N-methyl-3-chloroaniline: 3-CHLORO-N-METHYLANILINE is synthesized using 3-CHLORO-N-METHYLANILINE as a precursor, and it may have potential applications in the development of new drugs or drug candidates.
2. 2-[2-(N-methyl-3-chloroanilino)ethyl]-1,3-isoindolinedione: 3-CHLORO-N-METHYLANILINE is also derived from 3-CHLORO-N-METHYLANILINE and can be utilized in the synthesis of pharmaceutical agents with specific therapeutic properties.
3. N1-(3-chlorophenyl)-N1-methyl-1,2-ethanediamine dihydrochloride: 3-CHLORO-N-METHYLANILINE, obtained from 3-CHLORO-N-METHYLANILINE, can be used in the development of novel therapeutic agents with potential applications in medicine.

Upstream product

• 32111-92-5 N-(3-chlorophenyl)-N-methylcyanamide 
• 108-42-9 3-chloro-aniline 
• 74-88-4 methyl iodide 
• 7519-65-5 N-(3-chlorobenzylidene)aniline 
• 77-78-1 dimethyl sulfate 
• 139-71-9 m-chloroformanilide 
• 67-56-1 methanol 
• 72681-27-7 3'-Chlor-N-methyltoluanilid 
• 6848-13-1 3-chloro-N,N-dimethylaniline 
• 54766-53-9 N-(3-chlorophenyl)-N-methylacetamide 
• 60711-15-1 N-methyl-N-(3-chlorophenyl)carboxamide 
• 80179-78-8 methyl N-3-chloeophenyl-N-methylcarbamate 
• 79431-20-2 (3-Chloro-phenyl)-(dimethoxy-phenyl-methyl)-methyl-amine 
• 126799-85-7 3-chlorobenzylazide 

Downstream Products

• 4877-98-9 2-((3-chlorophenyl)(methyl)amino)ethan-1-ol 
• 55239-35-5 N-(3-chlorophenyl)-N-methylcarbamoyl chloride 
• 115943-90-3 3-chloro-N-methyl-4-nitroso-aniline 
• 4819-33-4 3-chloro-N-(2-chloro-ethyl)-N-methyl-aniline 
• 50838-39-6 (3-Chloro-phenyl)-methyl-thiocarbamic acid O-(1,2,3,4-tetrahydro-1,4-methano-naphthalen-6-yl) ester 
• 64797-65-5 3-[1-(3-Bromo-phenyl)-1-methyl-ethyl]-1-(3-chloro-phenyl)-1-methyl-urea 
• 64798-28-3 1-(3-Chloro-phenyl)-1-methyl-3-(1-methyl-1-naphthalen-1-yl-ethyl)-urea 
• 67103-16-6 C₁₈H₁₅ClN₂O₄ 
• 64062-71-1 3-(2-Methoxy-aethoxy-carbonyl-amino)-phenyl-N-methyl-3-chlor-carbanilat 
• 128408-10-6 N¹-methyl-N¹-(m-chloro-phenyl)-N²-phenylformamidine 
• 99942-71-9 N-(3-Chloro-phenyl)-N-methyl-N'-p-tolyl-acetamidine 
• 99942-83-3 N,N'-Bis-(3-chloro-phenyl)-N-methyl-acetamidine 
• 99942-68-4 N-(3-Chloro-phenyl)-N'-(4-methoxy-phenyl)-N-methyl-acetamidine 
• 92144-29-1 2,4-Diamino-quinazoline-6-sulfonic acid (3-chloro-phenyl)-methyl-amide 

Relevant academic research and scientific papers

Synthesis of 4-functionalized indoles via benzyne cyclization of N-(2- lithioallyl)-2-fluoroanilines

Treatment of N-(2-bromoallyl)-N-methyl-2-fluoroaniline with tert- butyllithium affords 1,3-dimethyl-4-lithioindole, via intramolecular addition to a tethered benzyne intermediate. Further reaction with electrophiles leads to 4-functionalized 3-methylindol

Electronically tuneable orthometalated RuII–NHC complexes as efficient catalysts for C–C and C–N bond formations via borrowing hydrogen strategy

The catalytic activities of a series of simple and electronically tuneable cyclometalated RuII–NHC complexes (2a–d) were explored in various C–C/N bond formations following the borrowing hydrogen process. Slight modifications in the ligand backbone were noted to tune the activities of these complexes. Among them, the complex 2d featuring a 1,2,4-triazolylidene donor with a 4-NO2–phenyl substituent displayed the highest activity for the coupling of diverse secondary and primary alcohols with a low catalyst loading of 0.01 mol% and a sub-stoichiometric amount of inexpensive KOH base. The efficacy of this simple system was further showcased in the challenging one-pot unsymmetrical double alkylation of secondary alcohols using different primary alcohols. Moreover, the complex 2d also effectively catalyses the selective mono-N-methylation of various aromatic and aliphatic primary amines using methanol to deliver a range of N-methyl amines. Mechanistically, the β-alkylation reaction follows a borrowing hydrogen pathway which was established by the deuterium labelling experiment in combination with various control experiments. Intriguingly, in situ1H NMR and ESI-MS analyses evidently suggested the involvement of a Ru–H species in the catalytic cycle and further, the kinetic studies revealed a first order dependence of the reaction rate on the catalyst as well as the alcohol concentrations.

Iodine-Promoted Metal-Free Cyclization and O/S Exchange of Acrylamides with Thiuram: One-Step Synthesis of Quinolino-2-thiones

A one-step cyclization and O/S exchange reaction of readily available acrylamides in the presence of iodine and thiuram has been developed. The reaction provides an efficient approach for the synthesis of highly important heterocycle quinolino-2-thiones with diverse substitution patterns.

Method for realizing N-alkylation by using alcohols as carbon source under photocatalysis

The invention discloses a method for realizing N-alkylation by using alcohols as a carbon source under photocatalysis, and belongs to the technical field of catalytic synthesis. Alcohol, a substrate raw material and a catalyst are placed in a reaction device, ultraviolet and/or visible light irradiation is carried out in an inert atmosphere, after the irradiation is finished, solid-liquid separation is carried out to remove the catalyst, and an N-alkylation product can be obtained through extraction, distillation and purification, wherein the substrate raw material comprises any one of an amine compound, an aromatic nitro compound or an aromatic nitrile compound, the alcohol comprises any one or more of soluble primary alcohols, and the catalyst is metal oxide/titanium dioxide or metal sulfide/titanium dioxide. The method is simple and easy to operate, can be used for efficient photocatalysis one-pot multi-step hydrogenation N-alkylation reaction, and is mild in reaction condition, high in chemical selectivity of N-alkylamine, good in catalyst stability and easy to recycle.

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.

Synthesis of: N -methylated amines from acyl azides using methanol

The transformation of acyl azide derivatives into N-methylamines was developed using methanol as the C1 source via the one-pot Curtius rearrangement and borrowing hydrogen methodology. Following this protocol, various functionalised N-methylated amines were synthesized using the (NNN)Ru(ii) complex from carboxylic acids via an acyl azide intermediate. Several kinetic studies and DFT calculations were carried out to support the mechanism and also to determine the role of the Ru(ii) complex and base in this transformation.

Selective N -monomethylation of primary anilines with the controllable installation of N -CH2D, N -CHD2, and N -CD3units

The selective N-monomethylation of primary anilines was realized by the use of the Me3N-BH3/N,N-dimethylformamide (DMF) system as the methyl source. This method also allows for the controllable introduction of N-CH2D, N-CHD2, and N-CD3 units with high lev

Highly Efficient Binuclear Copper-catalyzed Oxidation of N,N-Dimethylanilines with O2

A binuclear copper-salicylate complex, [Cu(Sal)2(NCMe)]2 (Sal=salicylate), was found to be an active catalyst for the oxidation of N,N-dimethylanilines by O2, affording the corresponding N-methyl-N-phenylformamides as major products. The reactions were carried out with a O2 balloon and the S/C (substrate/catalyst ratio) of the model reaction could be up to 1×105, providing a practical and highly efficient catalytic protocol for accessing N-methyl-N-phenylformamides.

Selective mono-N-methylation of nitroarenes with methanol catalyzed by atomically dispersed NHC-Ir solid assemblies

A series of N-heterocyclic carbene-iridium (NHC-Ir) coordination assemblies based on bis-pyrenoimidazolium salts are prepared, and shown to function as efficient solid molecular catalysts in selective mono-N-methylation of nitroarenes with methanol under mild conditions. The atomically dispersed active Ir(I) centers and the large π-conjugation rings endow the solid catalysts with an exceptionally high activity and selectivity for a broad substrate scope. Such solid NHC-Ir coordination assemblies are robust, which can be easily recovered and reused more than 10 runs without significant loss of their catalytic activity and selectivity. When combined with a subsequent formylation using the same solid catalysts under ambient conditions, this novel protocol can afford diverse formamides in excellent yields, further highlighting the applicability of the present solid catalysts for an efficient diversification of nitroarenes to a broad number of functional amines.

Bimetallic Bis-NHC-Ir(III) Complex Bearing 2-Arylbenzo[d]oxazolyl Ligand: Synthesis, Catalysis, and Bimetallic Effects

Herein, an unprecedented bimetallic bis-NHC Cp*Ir complex 1 bearing 2-arylbenzo[d]oxazolyl and NHC ligands is reported. A significant increase in activity was observed for N-methylation of amines and reduction of aldehydes with MeOH catalyzed by 1 compared to the monometallic analogues (2-11). Under the optimal conditions, it showed to be highly effective in N-methylation of nitroarenes with MeOH as both C1 and H2 source. Substrates, including aromatic amines, ketones, and nitro compounds with various functional groups, can be well-tolerated. Mechanistic studies and DFT calculation highlight the significance of bimetallic centers cooperativity.