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 
• 104-94-9 4-methoxy-aniline 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 104292-31-1 N-benzyl-4-methoxy-N,N-dimethylbenzenaminium bromide 
• 7732-18-5 water 
• 28441-91-0 tri-N-methyl-p-anisidinium; chloride 
• 35466-86-5 (2-methoxy)ethyl methyl carbonate 
• 141814-27-9 2-(2-Methoxyethoxy)ethyl methyl carbonate 
• 123-30-8 4-amino-phenol 
• 616-38-6 carbonic acid dimethyl ester 
• 13061-96-6 dihydroxy-methyl-borane 
• 623-12-1 4-chloromethoxybenzene 

Downstream Products

• 35813-38-8 N-(4-methoxyphenyl)-N-methylacetamide 
• 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 
• 4173-65-3 3-[(4-methoxyphenyl)amino]-1-phenylpropan-1-one 
• 63352-81-8 3-[(4-Methoxy-phenyl)-(3-oxo-3-phenyl-propyl)-amino]-1-phenyl-propan-1-one 
• 89787-33-7 3-((4-methoxyphenyl)(methyl)amino)-1-phenylpropan-1-one 
• 76259-14-8 2,8-Dichloro-5,11-dimethyl-5,6,11,12-tetrahydro-dibenzo[b,f][1,5]diazocine 
• 76259-09-1 3,8-dimethoxy-5,11-dimethyl-5,6,11,12-tetrahidrodibenzo<1,5>diazocine 
• 85021-24-5 2-Chloro-8-methoxy-5,11-dimethyl-5,6,11,12-tetrahydro-dibenzo[b,f][1,5]diazocine 
• 88825-18-7 Toluene-4-sulfonatebenzyl-(4-methoxy-phenyl)-dimethyl-ammonium; 
• 88801-98-3 Benzenesulfonatebenzyl-(4-methoxy-phenyl)-dimethyl-ammonium; 
• 88801-97-2 4-Chloro-benzenesulfonatebenzyl-(4-methoxy-phenyl)-dimethyl-ammonium; 
• 116015-94-2 [4-(Ethoxycarbonyl-{[(4-methoxy-phenyl)-methyl-amino]-methyl}-amino)-phenyl]-carbamic acid ethyl ester 
• 5466-93-3 diethyl 1,4-phenylenediamine-N,N'-dicarboxylate 

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.

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.

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.

Metal-Free Deoxygenation of Amine N-Oxides: Synthetic and Mechanistic Studies

We report herein an unprecedented combination of light and P(III)/P(V) redox cycling for the efficient deoxygenation of aromatic amine N-oxides. Moreover, we discovered that a large variety of aliphatic amine N-oxides can easily be deoxygenated by using only phenylsilane. These practically simple approaches proceed well under metal-free conditions, tolerate many functionalities and are highly chemoselective. Combined experimental and computational studies enabled a deep understanding of factors controlling the reactivity of both aromatic and aliphatic amine N-oxides.

Visible-Light-Induced C(sp2)-C(sp3) Cross-Dehydrogenative-Coupling Reaction of N-Heterocycles with N-Alkyl- N-methylanilines under Mild Conditions

Disclosed herein is a cross-dehydrogenative-coupling reaction of N-heterocycles including 1,2,4-triazine-3,5(2H, 4H)-diones and quinoxaline-2(1H)-ones with N-methylanilines to form C(sp2)-C(sp3) under visible-light illumination and ambient air at room temperature. In this process, easily available Ru(bpy)3Cl2·6H2O serves as the catalyst, and air acts as the green oxidant. This method features high atom economy, environmental friendliness, and convenient operation and provides an efficient and practical access to aminomethyl-substituted N-heterocycles with extensive functional group compatibility in 40-86% yields.

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.