403-46-3

Usage

Uses

Used in Pharmaceutical Industry:
4-FLUORO-N,N-DIMETHYLANILINE is utilized as an intermediate in the synthesis of various pharmaceuticals, contributing to the development of new medications due to its unique chemical structure.
Used in Dye Industry:
4-FLUORO-N,N-DIMETHYLANILINE serves as an intermediate for the production of dyes, where its specific molecular features enhance the color properties and stability of the resulting dyes.
Used in Agrochemical Industry:
4-FLUORO-N,N-DIMETHYLANILINE is employed as an intermediate in the synthesis of agrochemicals, playing a role in the development of effective and targeted pest control agents.
Used as a Reagent in Organic Chemical Reactions:
Due to its reactive nature, 4-FLUORO-N,N-DIMETHYLANILINE is used as a reagent in various organic chemical reactions, facilitating the synthesis of a range of organic compounds.

Upstream product

• 371-40-4 4-fluoroaniline 
• 74-88-4 methyl iodide 
• 874-52-2 N,N-dimethylaniline N-oxide 
• 462-35-1 N-(ethyl)acetonitrilium tetrafluoroborate 
• 64-18-6 formic acid 
• 350-46-9 4-Fluoronitrobenzene 
• 459-59-6 4-fluoro-N-methylaniline 
• 50-00-0 formaldehyd 
• 455-08-3 p-FC₆H₄NMe₃(+)*I(-) 
• 130445-20-4 4-Fluoro-N,N-dimethylaniline N-oxide 
• 67-56-1 methanol 
• 124-38-9 carbon dioxide 
• 616-38-6 carbonic acid dimethyl ester 
• 67-68-5 dimethyl sulfoxide 

Downstream Products

• 329-09-9 4-fluoro-tri-N-methyl-anilinium; methyl sulfate 
• 455-08-3 p-FC₆H₄NMe₃(+)*I(-) 
• 773-91-1 5-fluoro-1-methylisatin 
• 333725-83-0 N-{2-[(2-dimethylamino-5-fluoro-phenyl)-(pyridin-2-ylamino)-methyl]-4-fluoro-phenyl}-N-methyl-formamide 
• 121-69-7 N,N-dimethyl-aniline 
• 63029-13-0 4'-(4-aminophenoxy)-N,N-dimethyl benzenamine 
• 864910-76-9 2-((4-fluorophenyl)(methyl)amino)acetonitrile 
• 840-57-3 2-(p-dimethylaminophenyl)benzoxazole 
• 530-44-9 4-(Dimethylamino)benzophenone 
• 214360-58-4 2-(4-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 95752-87-7 5,5-dimethyl-2-(4-(N,N-dimethylamino)phenyl)-1,3,2-dioxaborinane 

Relevant academic research and scientific papers

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.

Simplified preparation of a graphene-co-shelled Ni/NiO@C nano-catalyst and its application in theN-dimethylation synthesis of amines under mild conditions

The development of Earth-abundant, reusable and non-toxic heterogeneous catalysts to be applied in the pharmaceutical industry for bio-active relevant compound synthesis remains an important goal of general chemical research.N-methylated compounds, as one of the most essential bioactive compounds, have been widely used in the fine and bulk chemical industries for the production of high-value chemicals. Herein, an environmentally friendly and simplified method for the preparation of graphene encapsulated Ni/NiO nanoalloy catalysts (Ni/NiO@C) was developed for the first time, for the highly selective synthesis ofN-methylated compounds using various functional amines and aldehydes under easy to handle, and industrially applicable conditions. A large number of primary and secondary amines (more than 70 examples) could be converted to the correspondingN,N-dimethylamines with the participation of different functional aldehydes, with an average yield of over 95%. A gram-scale synthesis also demonstrated a similar yield when compared with the benchmark test. In addition, it was further proved that the catalyst could easily be recycled because of its intrinsic magnetism and reused up to 10 times without losing its activity and selectivity. Also, for the first time, the tandem synthesis ofN,N-dimethylamine products in a one-pot process, using only a single earth-abundant metal catalyst, whose activity and selectivity were more than 99% and 94%, respectively, for all tested substrates, was developed. Overall, the advantages of this newly developed method include operational simplicity, high stability, easy recyclability, cost-effectiveness of the catalyst, and good functional group compatibility for the synthesis ofN-methylation products as well as the industrially applicable tandem synthesis process.

Nickel-Catalyzed Amination of Aryl Chlorides with Amides

A nickel-catalyzed amination of aryl chlorides with diverse amides via C-N bond cleavage has been realized under mild conditions. A broad substrate scope with excellent functional group tolerance at a low catalyst loading makes the protocol powerful for synthesizing various aromatic amines. The aryl chlorides could selectively couple to the amino fragments rather than the carbonyl moieties of amides. Our protocol complements the conventional amination of aryl chlorides and expands the usage of inactive amides.

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.

Fe(III)-catalyzed Oxidative Povarov Reaction with Molecular Oxygen Oxidant

The synthesis of tetrahydroquinoline derivatives from dimethyl anilines and enamides has been developed by Fe(III)-phenanthroline complex under aerobic condition. The oxidation of tertiary anilines involving a single electron transfer of Fe(phen)3(PF6)3 afforded the iminium ion intermediate, which reacted with electron-rich alkenes to build a six-membered N-heterocycles containing quaternary carbon center via the oxidative Povarov reaction process.

Photocatalytic carbocarboxylation of styrenes with CO2for the synthesis of γ-aminobutyric esters

Metal-free photoredox-catalyzed carbocarboxylation of various styrenes with carbon dioxide (CO2) and amines to obtain γ-aminobutyric ester derivatives has been developed (up to 91% yield, 36 examples). The radical anion of (2,3,4,6)-3-benzyl-2,4,5,6-tetra(9H-carbazol-9-yl)benzonitrile (4CzBnBN) possessing a high reduction potential (?1.72 Vvs.saturated calomel electrode (SCE)) easily reduces both electron-donating and electron-withdrawing group-substituted styrenes.

Trialkylammonium salt degradation: Implications for methylation and cross-coupling

Trialkylammonium (most notably N,N,N-trimethylanilinium) salts are known to display dual reactivity through both the aryl group and the N-methyl groups. These salts have thus been widely applied in cross-coupling, aryl etherification, fluorine radiolabelling, phase-transfer catalysis, supramolecular recognition, polymer design, and (more recently) methylation. However, their application as electrophilic methylating reagents remains somewhat underexplored, and an understanding of their arylation versus methylation reactivities is lacking. This study presents a mechanistic degradation analysis of N,N,N-trimethylanilinium salts and highlights the implications for synthetic applications of this important class of salts. Kinetic degradation studies, in both solid and solution phases, have delivered insights into the physical and chemical parameters affecting anilinium salt stability. 1H NMR kinetic analysis of salt degradation has evidenced thermal degradation to methyl iodide and the parent aniline, consistent with a closed-shell SN2-centred degradative pathway, and methyl iodide being the key reactive species in applied methylation procedures. Furthermore, the effect of halide and non-nucleophilic counterions on salt degradation has been investigated, along with deuterium isotope and solvent effects. New mechanistic insights have enabled the investigation of the use of trimethylanilinium salts in O-methylation and in improved cross-coupling strategies. Finally, detailed computational studies have helped highlight limitations in the current state-of-the-art of solvation modelling of reaction in which the bulk medium undergoes experimentally observable changes over the reaction timecourse. This journal is

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.

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.

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.