932-32-1

Usage

Uses

Used in Chemical Synthesis:
2-Chloro-N-methylaniline is used as a key intermediate in the synthesis of various organic compounds and pharmaceuticals. Its reactivity and functional groups make it a versatile building block for the development of new molecules with potential applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-chloro-N-methylaniline is used as a starting material for the synthesis of various drugs and drug candidates. Its ability to form a wide range of derivatives allows for the creation of molecules with specific therapeutic properties, making it a valuable component in drug discovery and development.
Used in Dye and Pigment Industry:
2-Chloro-N-methylaniline is also used in the dye and pigment industry for the production of various colorants. Its chemical structure allows for the formation of a variety of colored compounds, which can be used in the manufacturing of textiles, plastics, and other materials that require coloration.
Used in the Production of 1-Methyl-2-Thioacetylpyrrole:
2-Chloro-N-methylaniline is used to produce 1-methyl-2-thioacetylpyrrole, a compound of interest in various chemical applications. This synthesis is carried out in the presence of reagent Lawesson's reagent and solvent tetrahydrofuran, demonstrating the versatility of 2-chloro-N-methylaniline in chemical reactions and its potential use in the synthesis of other valuable compounds.

InChI:InChI=1/C7H8ClN/c1-9-7-5-3-2-4-6(7)8/h2-5,9H,1H3

Upstream product

• 876479-72-0 3-phenyl-propionic acid-(2-chloro-N-methyl-anilide) 
• 95-51-2 o-chloroaniline 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 112160-74-4 acetic acid-(2,4,N-trichloro-anilide) 
• 100-61-8 N-methylaniline 
• 91192-73-3 (2-chloroanilino)methylsuccinimide 
• 7647-01-0 hydrogenchloride 
• 77102-32-0 O-allyl-N-methyl-N-phenyl-hydroxylamine 
• 13506-15-5 N-(2-chloro-phenyl)-formimidic acid ethyl ester 
• 50-00-0 formaldehyd 
• 67-56-1 methanol 
• 616-38-6 carbonic acid dimethyl ester 
• 82925-50-6 Methylene-ortho-chloroaniline 

Downstream Products

• 55239-76-4 N-methyl-N-(2-chlorophenyl)carbamoyl chloride 
• 93646-33-4 3-methyl-crotonic acid-(2-chloro-N-methyl-anilide) 
• 855244-03-0 2-nitro-benzoic acid-(2-chloro-N-methyl-anilide) 
• 66124-41-2 N,N'-Dimethyl-N-(2-chloro)phenylbenzamidine 
• 74585-33-4 N-(2-chlorophenyl)-N-methyl-2-phenylacetic acid amide 
• 1484-12-4 N-methylcarbazole 
• 24075-47-6 2,9-dimethyl-9H-carbazole 
• 796964-13-1 1-methyl-2-phenyl-3-propyl-1H-indole 
• 1104642-36-5 N-methyl N-(2-chlorophenyl) 6-acetoxymethyl-2-oxo-2H-1-benzopyran-3-carboxamide 
• 1201761-81-0 (2-chloro-phenyl)-(2,2-dimethylcyclopropyl)methylamine 
• 1018447-47-6 methyl 3-{[(2-chlorophenyl)(methyl)amino]methyl}benzoate 
• 202057-10-1 2-chlorophenyl{3-[2-chlorophenyl(methyl)amino]-1H-isoindol-1-ylidene}methylammonium perchlorate 

Relevant academic research and scientific papers

Novel hybrid conjugates with dual estrogen receptor α degradation and histone deacetylase inhibitory activities for breast cancer therapy

Hormone therapy targeting estrogen receptors is widely used clinically for the treatment of breast cancer, such as tamoxifen, but most of them are partial agonists, which can cause serious side effects after long-term use. The use of selective estrogen receptor down-regulators (SERDs) may be an effective alternative to breast cancer therapy by directly degrading ERα protein to shut down ERα signaling. However, the solely clinically used SERD fulvestrant, is low orally bioavailable and requires intravenous injection, which severely limits its clinical application. On the other hand, double- or multi-target conjugates, which are able to synergize antitumor activity by different pathways, thus may enhance therapeutic effect in comparison with single targeted therapy. In this study, we designed and synthesized a series of novel dual-functional conjugates targeting both ERα degradation and histone deacetylase inhibiton by combining a privileged SERD skeleton 7-oxabicyclo[2.2.1]heptane sulfonamide (OBHSA) with a histone deacetylase inhibitor side chain. We found that substituents on both the sulfonamide nitrogen and phenyl group of OBHSA unit had significant effect on biological activities. Among them, conjugate 16i with N-methyl and naphthyl groups exhibited potent antiproliferative activity against MCF-7 cells, and excellent ERα degradation activity and HDACs inhibitory ability. A further molecular docking study indicated the interaction patterns of these conjugates with ERα, which may provide guidance to design novel SERDs or PROTAC-like SERDs for breast cancer therapy.

Halogenated method of aromatic compound

The invention belongs to the field of organic synthesis, and particularly relates to synthesis of aromatic halogens, in particular to arylamine. The invention discloses a synthesis method of a corresponding ortho-halogenated product from aromatic compounds such as carbazole and phenol. The method comprises the following steps: adding a metal sulfonate salt catalyst, aromatic amine, carbazole, phenol and other hydrogen - heteroatom-containing aromatic compound reaction substrates, a halogenation reagent and a reaction solvent at a specific reaction temperature. After the drying agent is dried, the yield of the reaction product and the nuclear magnetic characterization determining structure are determined by column chromatography. The reaction product yield is determined by gas chromatography. By adopting the method, under the cheap metal salt catalyst, a plurality of ortho-substituted brominated and chloro products can be obtained with moderate to excellent yield.

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.

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.

Iron-Catalyzed Regioselective α-C-H Alkylation of N-Methylanilines: Cross-Dehydrogenative Coupling between Unactivated C(sp3)-H and C(sp3)-H Bonds via a Radical Process

The iron-catalyzed α-C-H alkylation of N-methylanilines without any directing group by cross-dehydrogenative coupling between unactivated C(sp3)-H and C(sp3)-H bonds has been established for the first time, which provides a good complement to C(sp3)-H activation reactions and expands the field of Fe-catalyzed C-H functionalizations. Many different C(sp3)-H bonds in cyclic alkanes, cyclic ethers, and toluene derivatives can be used as coupling partners. Mechanistic investigations including the radical reaction process, the main role of various reagents, and the kinetic isotope effect experiment were also described.

N -Methylation of ortho -substituted aromatic amines with methanol catalyzed by 2-arylbenzo [d] oxazole NHC-Ir(iii) complexes

Seven new chelated cyclometalated Ir complexes of ABON,P, ABON,O, and ABON,C(carbene) based on a rigid and tunable 2-arylbenzo[d]oxazole backbone have been prepared for the N-methylation of amines. Among these three coordinated modes, ABON,C(carbene)-chelated iridium-based catalysts exhibited good performance in the monomethylation of aromatic amines with methanol (MeOH) as the green methylation reagent. The steric-modified synthesis of ABON,C(carbene) complexes was described. The most active ABON,C(carbene) complex with marginal steric hindrance as a catalyst was obtained from the benzoxazole ring without a substituent and methyl group of the benzimidazole ring on the N-heterocyclic carbene (NHC) ligand. A variety of amines including para- and meta-substituted aromatic amines, as well as heterocyclic amines, were formulated as suitable substrates. Importantly, this catalyst considerably promoted the yield of the N-methylation of ortho-substituted aromatic amines. Controlled kinetic experiments and deuterium-labeling reactions of these ortho-substituted amines were conducted under optimized conditions. On the basis of the experimental results, a plausible mechanism was proposed.

Manufacturing method for halogen substituted N-methylaniline

The present invention relates to a method for manufacturing halogen-substituted N-methylaniline from halogen-substituted aniline. When halogen-substituted N-methylaniline is manufactured by using the method of the present invention, it is possible to manufacture halogen-substituted N-methylaniline without using existing methoxide sodium which has low chemical stability and is expensive, by using a low-cost base having excellent chemical stability such as potassium hydroxide or sodium hydroxide. Therefore, it is possible to reduce costs in a manufacturing process and to produce N-methylaniline with a high yield and high purity, thereby being useful for mass production as a raw material for herbicide metamifop synthesis.COPYRIGHT KIPO 2019

The design, synthesis and evaluation of selenium-containing 4-anilinoquinazoline hybrids as anticancer agents and a study of their mechanism

Inhibition of tubulin polymerization is one of the significant strategies in the treatment of cancer. Inspired by the excellent antitumor activity of EP128495 and the beneficial biological activities of selenium compounds, a series of new selenium-containing 4-anilinoquinazoline hybrids were synthesized and evaluated as tubulin polymerization inhibitors. An anti-proliferative activity assay showed that most of the compounds inhibited human sensitive cancer cells at low nanomolar concentrations. A mechanism study revealed that the optimal compound 5a disrupted microtubule dynamics, decreased the mitochondrial membrane potential and arrested HeLa cells in the G2/M phase, finally resulting in cellular apoptosis.

Stereospecific copper-catalyzed domino ring opening and sp3 C-H functionalization of activated aziridines with N-alkylanilines

Copper efficiently catalyzed nucleophilic ring opening, sp3 C-H functionalization, and C-N bond formation in the presence of tert-butyl hydroperoxide to afford functionalized imidazolidines starting from N-sulfonylaziridines and Nalkylanilines. The products were obtained in high optical purities (95 → 99% ee) with excellent functional group tolerance.

Formation of Phenyliodonio-Substituted Spirofurooxindole Trifluoroacetates from N-Substituted 3-Oxopentanediamides via Phenyliodine Bis(trifluoroacetate)-Mediated Oxidative Cascade Reactions

The reaction of N-substituted 3-oxopentanediamides with phenyliodine bis(trifluoroacetate) (PIFA) was found to give a novel class of phenyliodonio-substituted spirofurooxindole trifluoroacetates under metal-free conditions. The reaction is postulated to proceed via a cascade process involving an oxidative C—O bond formation, an oxidative C—C bond formation and a final iodination step. (Figure presented.).