701-56-4

Usage

Uses

Used in Pharmaceutical Synthesis:
(4-METHOXY-PHENYL)-DIMETHYL-AMINE is utilized as a building block in the synthesis of pharmaceutical drugs. Its unique structure allows it to be a key component in the creation of various organic compounds, contributing to the development of new medications.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (4-METHOXY-PHENYL)-DIMETHYL-AMINE is employed for its potential applications in drug discovery. Its chemical properties make it a valuable candidate for the exploration of new therapeutic agents and the enhancement of existing ones.
Used in Organic Chemistry Research:
(4-METHOXY-PHENYL)-DIMETHYL-AMINE is also used as a research compound in organic chemistry. Its reactivity and structural features are of interest to scientists who are investigating new reactions and mechanisms, potentially leading to advancements in synthetic methodologies and the discovery of novel chemical entities.

InChI:InChI=1/C9H13NO/c1-10(2)8-4-6-9(11-3)7-5-8/h4-7H,1-3H3

Upstream product

• 67-56-1 methanol 
• 17310-99-5 4-methoxy-N,N,N-trimethylbenzenaminium iodide 
• 150-75-4 N-methyl-p-aminophenol 
• 131-11-3 phthalic acid dimethyl ester 
• 512-56-1 trimethyl phosphite 
• 104-94-9 4-methoxy-aniline 
• 50-00-0 formaldehyd 
• 64-18-6 formic acid 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 698-69-1 4-chloro-N,N-dimethylaniline 
• 865-33-8 potassium methanolate 
• 31468-21-0 9-methylfluorenyl carboanion 
• 104292-35-5 N-(m-cyanobenzyl)-N,N-dimethyl-p-methoxyanilinium bromide 

Downstream Products

• 57205-99-9 4-methoxy-N-methyl-2,6,N-trinitro-aniline 
• 103854-11-1 4-methoxy-N,N-dimethyl-3-nitro-aniline 
• 619-60-3 4-(N,N-dimethylamino)phenol 
• 90559-67-4 4-methoxy-N,N-dimethyl-2,6-dinitro-aniline 
• 857600-90-9 4-methoxy-N-methyl-2,6-dinitro-N-nitroso-aniline 
• 34418-89-8 4-methoxy-N,N-dimethylaniline N-oxide 
• 60049-83-4 4-Methoxy-2-nitro-N,N-dimethylbenzeneamine 
• 861525-58-8 4-methoxy-N,N-dimethyl-3,5-dinitro-aniline 
• 35813-38-8 N-(4-methoxyphenyl)-N-methylacetamide 
• 67759-05-1 N-allyl-4-methoxy-N,N-dimethylbenzenaminium bromide 
• 17310-99-5 4-methoxy-N,N,N-trimethylbenzenaminium iodide 
• 98526-35-3 (4aS,9aS)-6-Methoxy-9-methyl-2,3,4,4a,9,9a-hexahydro-pyrano[2,3-b]indole 
• 5961-59-1 N-methyl-N-(4-methoxyphenyl)amine 
• 5279-51-6 4-methoxy-N-methylformanilide 

Relevant academic research and scientific papers

Perchlorate Esters. 4. Kinetics and Mechanism of the Reactions of Alkyl Perchlorates with N,N-Dimethylanilines in Benzene

The reactions in benzene of methyl, ethyl, and isopropyl perchlorates with N,N-dimethylanilines, to yield precipitates of the quaternary anilinium perchlorate, proceed with second-order kinetics and exhibit a large negative entropy of activation.At 25.0 d

N,N-DIMETHYL-p-ANISIDINUM CATION. ESR EVIDENCE FOR INTERMOLECULAR SPIN-LONE PAIR INTERACTION

ESR characterisation of N,N-dimethyl-p-anisidinum dimer radical cation is reported.

A Mild Heteroatom (O -, N -, and S -) Methylation Protocol Using Trimethyl Phosphate (TMP)-Ca(OH) 2Combination

A mild heteroatom methylation protocol using trimethyl phosphate (TMP)-Ca(OH)2combination has been developed, which proceeds in DMF, or water, or under neat conditions, at 80 °C or at room temperature. A series of O-, N-, and S-nucleophiles, including phenols, sulfonamides, N-heterocycles, such as 9H-carbazole, indole derivatives, and 1,8-naphthalimide, and aryl/alkyl thiols, are suitable substrates for this protocol. The high efficiency, operational simplicity, scalability, cost-efficiency, and environmentally friendly nature of this protocol make it an attractive alternative to the conventional base-promoted heteroatom methylation procedures.

Additive-free selective methylation of secondary amines with formic acid over a Pd/In2O3 catalyst

Formic acid is used as the sole carbon and hydrogen source in the methylation of aromatic and aliphatic amines to methylamines. The reaction proceeds via a formylation/transfer hydrogenation pathway over a solid Pd/In2O3 catalyst without the need for any additive.

CO2-tuned highly selective reduction of formamides to the corresponding methylamines

We herein describe an efficient, CO2-tuned and highly selective C-O bond cleavage of N-methylated formanilides. With easy-to-handle and commercially available NaBH4 as the reductant, a variety of formanilides could be turned into the desired tertiary amines in moderate to excellent yields. The role of CO2 has been investigated in detail, and the mechanism is proposed on the basis of experiments.

Catalytic SNAr Hydroxylation and Alkoxylation of Aryl Fluorides

Nucleophilic aromatic substitution (SNAr) is a powerful strategy for incorporating a heteroatom into an aromatic ring by displacement of a leaving group with a nucleophile, but this method is limited to electron-deficient arenes. We have now established a reliable method for accessing phenols and phenyl alkyl ethers via catalytic SNAr reactions. The method is applicable to a broad array of electron-rich and neutral aryl fluorides, which are inert under classical SNAr conditions. Although the mechanism of SNAr reactions involving metal arene complexes is hypothesized to involve a stepwise pathway (addition followed by elimination), experimental data that support this hypothesis is still under exploration. Mechanistic studies and DFT calculations suggest either a stepwise or stepwise-like energy profile. Notably, we isolated a rhodium η5-cyclohexadienyl complex intermediate with an sp3-hybridized carbon bearing both a nucleophile and a leaving group.

Photocatalytic Water-Splitting Coupled with Alkanol Oxidation for Selective N-alkylation Reactions over Carbon Nitride

Photocatalytic water splitting technology (PWST) enables the direct use of water as appealing “liquid hydrogen source” for transfer hydrogenation reactions. Currently, the development of PWST-based transfer hydrogenations is still in an embryonic stage. Previous reports generally centered on the rational utilization of the in situ generated H-source (electrons) for hydrogenations, in which photogenerated holes were quenched by sacrificial reagents. Herein, the fully-utilization of the liquid H-source and holes during water splitting is presented for photo-reductive N-alkylation of nitro-aromatic compounds. In this integrate system, H-species in situ generated from water splitting were designed for nitroarenes reduction to produce amines, while alkanols were oxidized by holes for cascade alkylating of anilines as well as the generated secondary amines. More than 50 examples achieved with a broad range scope validate the universal applicability of this mild and sustainable coupling approach. The synthetic utility of this protocol was further demonstrated by the synthesis of existing pharmaceuticals via selective N-alkylation of amines. This strategy based on the sustainable water splitting technology highlights a significant and promising route for selective synthesis of valuable N-alkylated fine chemicals and pharmaceuticals from nitroarenes and amines with water and alkanols.

Mesoionic N-heterocyclic olefin catalysed reductive functionalization of CO2for consecutiveN-methylation of amines

A mesoionic N-heterocyclic olefin (mNHO) was introduced as a metal-free catalyst for the reductive functionalization of CO2leading to consecutive doubleN-methylation of primary amines in the presence of 9-borabicyclo[3.3.1]nonane (9-BBN). A wide range of secondary amines and primary amines were successfully methylated under mild conditions. The catalyst sustained over six successive cycles ofN-methylation of secondary amines without compromising its activity, which encouraged us to check its efficacy towards doubleN-methylation of primary amines. Moreover, this method was utilized for the synthesis of two commercially available drug molecules. A detailed mechanistic cycle was proposed by performing a series of control reactions along with the successful characterisation of active catalytic intermediates either by single-crystal X-ray study or by NMR spectroscopic studies in association with DFT calculations.

Utilization of renewable formic acid from lignocellulosic biomass for the selective hydrogenation and/or N-methylation

Lignocellulosic biomass is one of the most abundant renewable sources in nature. Herein, we have developed the utilization of renewable formic acid from lignocellulosic biomass as a hydrogen source and a carbon source for the selective hydrogenation and further N-methylation of various quinolines and the derivatives, various indoles under mild conditions in high efficiencies. N-methylation of various anilines is also developed. Mechanistic studies indicate that the hydrogenation occurs via a transfer hydrogenation pathway.

Borane-Trimethylamine Complex as a Reducing Agent for Selective Methylation and Formylation of Amines with CO2

We report herein that a borane-trimethylamine complex worked as an efficient reducing agent for the selective methylation and formylation of amines with 1 atm CO2 under metal-free conditions. 6-Amino-2-picoline serves as a highly efficient catalyst for the methylation of various secondary amines, whereas in its absence, the formylation of primary and secondary amines was achieved in high yield with high chemoselectivity. Mechanistic studies suggest that the 6-amino-2-picoline-borane catalytic system operates like an intramolecular frustrated Lewis pair to activate CO2.