10541-78-3

Usage

Uses

Used in Dye and Pigment Industry:
2-Methoxy-N-methylaniline is used as a chemical intermediate for the synthesis of ortho-toluidine-derived dyes and organic pigments. Its presence in these compounds contributes to their color and stability, making it an essential component in the production process.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Methoxy-N-methylaniline serves as a precursor for the synthesis of various pharmaceuticals. Its unique chemical properties allow it to be transformed into active ingredients that can be used in the development of medications for different therapeutic applications.
Used in Pesticide Industry:
2-Methoxy-N-methylaniline is also utilized in the production of certain pesticides. Its chemical structure enables it to be incorporated into formulations that target specific pests, providing an effective means of crop protection.
However, it is crucial to note that exposure to 2-Methoxy-N-methylaniline has been linked to harmful effects on human health. Therefore, it is essential to implement appropriate safety measures and guidelines when handling this chemical compound in any industry to minimize potential risks.

InChI:InChI=1/C8H11NO/c1-9-7-5-3-4-6-8(7)10-2/h3-6,9H,1-2H3

Upstream product

• 483-64-7 methyl 3-methoxy-2-(methylamino)benzoate 
• 23896-88-0 formic acid o-anisidide 
• 485-27-8 3-methoxy-2-methylamino-benzoic acid 
• 90-04-0 2-methoxy-phenylamine 
• 74-88-4 methyl iodide 
• 124-41-4 sodium methylate 
• 77-78-1 dimethyl sulfate 
• 50-00-0 formaldehyd 
• 93-26-5 2-methoxyacetanilide 
• 85680-36-0 1,3,5-tris(o-methoxyphenyl)-1,3,5-triazacyclohexane 
• 10034-85-2 hydrogen iodide 
• 1226-64-8 1,3-bis-(2-methoxy-phenyl)-thiourea 
• 100-66-3 methoxybenzene 
• 592489-13-9 1,3-dimethyl-2-(2-methoxyphenylimino)imidazolidine 

Downstream Products

• 100390-66-7 N-(2-methoxyphenyl)-N-methyl-3-oxobutanamide 
• 10121-94-5 2-methoxy-N-methyl-4-phenylazo-aniline 
• 15258-52-3 N-allyl-N-methyl-o-anisidine 
• 102012-71-5 3-(2-benzyloxy-ethyl)-4-hydroxy-8-methoxy-1-methyl-1H-quinolin-2-one 
• 20451-54-1 N-(2-methoxyphenyl)-N-methylnitrous amide 
• 857600-62-5 2-methoxy-N-methyl-4-nitro-N-nitroso-aniline 
• 611-24-5 o-(N-methylamino)phenol 
• 151657-66-8 N-benzyl-N-methyl-o-anisidine 
• 93886-49-8 ethyl 2-hydroxy-3-(2-methoxy-N-methylanilino)-3-phenyl propionate 
• 38824-34-9 N-Methyl-N-propionyl-o-anisidin 
• 119787-86-9 N-(2-methoxyphenyl)-N-methyl-2-bromoacetamide 
• 779335-35-2 {[(2-methoxyphenyl)-methyl-carbamoyl]-methyl}-phosphonic acid diethyl ester 
• 119787-99-4 N-(2-Methoxyphenyl)-N-methyl-2,3-butadienamid 
• 119787-94-9 N-(2-Methoxyphenyl)-N-methyl-2-(triphenylphosphoranyliden)acetamid 

Relevant academic research and scientific papers

Evaluation of 4-phenylamino-substituted naphthalene-1,2-diones as tubulin polymerization inhibitors

A series of 4-phenylamino-substituted naphthalene-1,2-dione derivatives were prepared and evaluated as effective antiproliferative agents. MTT assays showed that the compounds with a methyl group on the nitrogen linker exhibited potent antiproliferative activities against human cancer cells. The mechanistic study revealed that these compounds could induce mitochondrial depolarization, which resulted in intracellular ROS production, and they also acted as tubulin polymerization inhibitors. Moreover, the typical compound could arrest A549 cells in the G2/M phase, resulting in cellular apoptosis and induced mitotic arrest in A549 cells through disrupting microtubule dynamics.

Palladium-catalyzed N-nitroso-directed C-H alkoxylation of arenes and subsequent formation of 2-alkoxy-N-alkylarylamines

(Chemical Equation Presented) A palladium-catalyzed direct ortho-alkoxylation of N-alkyl-N-nitrosoarylamines was developed in which alcohols were used as the alkoxylation reagents and PhI(OAc)2 was employed as the oxidant. The protocol was available for both primary and secondary alcohols. The products were transformed to o-alkoxy-N-alkylanilines expediently by a simple reduction.

Selective monomethylation of anilines by Cu(OAc)2-promoted cross-coupling with MeB(OH)2

N-Methylanilines are readily synthesized in high yields through the copper(ll)-promoted coupling of anilines and methylboronic acid. This method represents a new approach for the selective monomethylation of anilines, and it is the first reported example

Synthesis of N-Alkyl Anilines from Arenes via Iron-Promoted Aromatic C-H Amination

We report both an intermolecular C-H amination of arenes to access N-methylanilines and an intramolecular variant for the synthesis of tetrahydroquinolines. A newly developed, highly electrophilic aminating reagent was key for the direct synthesis of unprotected N-methylanilines from simple arenes. The reactions display a broad functional group tolerance and employ catalytic amounts of a benign iron salt under mild reaction conditions.

A Metal-Free Direct Arene C?H Amination

The synthesis of aryl amines via the formation of a C?N bond is an essential tool for the preparation of functional materials, active pharmaceutical ingredients and bioactive products. Usually, this chemical connection is only possible by transition metal-catalyzed reactions, photochemistry or electrochemistry. Here, we report a metal-free arene C?H amination using hydroxylamine derivatives under benign conditions. A charge transfer interaction between the aminating reagents TsONHR and the arene substrates enables the chemoselective amination of the arene, even in the presence of various functional groups. Oxygen was crucial for an effective conversion and its accelerating role for the electron transfer step was proven experimentally. In addition, this was rationalized by a theoretical study which indicated the involvement of a dioxygen-bridged complex with a “Sandwich-like” arrangement of the aromatic starting materials and the aminating agents at the dioxygen molecule. (Figure presented.).

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.

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.

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.

Palladacycle-Phosphine Catalyzed Methylation of Amines and Ketones Using Methanol

Methylation of amines and ketones with palladacycle precatalyst has been performed using methanol as an environmentally benign reagent. Various ketones and amines undergo methylation reaction to yield monomethylated amines or ketones in moderate to good isolated yields. Moreover, this protocol was tested for the chemoselective methylation of 4-aminobenzenesulfonamide. The scope of the reaction was further extended to the deuteromethylation of ketones.

DIRECT C-H AMINATION AND AZA-ANNULATION

In some aspects, the present disclosure provides methods of aminating an aromatic compound comprising reacting an aminating agent with an aromatic compound in the presence of a rhodium catalyst. In some embodiments, the methods may comprise aminating an aromatic compound which contains multiple different functional groups. The methods described herein may also be used to create bicyclic system comprising reacting an intramolecular aminating agent with an aromatic ring to obtain a second ring containing a nitrogen atom. In another aspect, the methods described herein may also be used to create a cyclic aliphatic cyclic/poly cyclic amine system comprising a reacting an intramolecular aminating agent by insertion into a C(sp3)-H bond.