1978-37-6

Usage

Uses

Used in Pharmaceutical Research:
3-FLUORO-N-METHYLANILINE is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique reactivity allows for the development of new drugs with improved efficacy and selectivity.
Used in Agrochemical Development:
3-FLUORO-N-METHYLANILINE is utilized as a building block in the creation of agrochemicals, such as pesticides and herbicides. Its ability to participate in various chemical reactions enables the design of novel and effective agrochemicals.
Used in Organic Synthesis:
3-FLUORO-N-METHYLANILINE serves as a versatile starting material in organic synthesis, allowing for the preparation of a wide range of organic compounds. Its reactivity and the presence of functional groups make it a valuable component in the synthesis of complex organic molecules.
Used in Fine Chemicals Production:
3-FLUORO-N-METHYLANILINE is employed as a precursor in the production of fine chemicals, which are high-purity chemicals used in various industries, such as fragrances, dyes, and specialty chemicals. Its unique properties contribute to the development of high-quality fine chemicals with specific applications.

InChI:InChI=1/C7H8FN/c1-9-7-4-2-3-6(8)5-7/h2-5,9H,1H3

Upstream product

• 1428-10-0 N-(3-fluorophenyl)formamide 
• 372-19-0 meta-fluoroaniline 
• 643735-24-4 N-(3-fluorophenyl)-N-methylformamide 
• 74-88-4 methyl iodide 
• 67-56-1 methanol 
• 50-00-0 formaldehyd 
• 402-67-5 3-fluoro-1-nitrobenzene 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 55239-44-6 N-(3-fluorophenyl)-N-methylcarbamoyl chloride 
• 87433-20-3 N-(3-fluorophenyl)-N-methyl-4-toluenesulfinamide 
• 113734-42-2 3-fluoro-N-methyl-N-benzylaniline 
• 100-61-8 N-methylaniline 
• 182417-73-8 DPI-3290 
• 226411-09-2 4-(N-benzyl-N-methylamino)-2-fluorobenzaldehyde 
• 226411-14-9 [4-(2-amino-propyl)-3-fluoro-phenyl]-benzyl-methyl-amine 
• 226411-04-7 2-chloro-N-<1-(4-N-methyl-N-benzylamino-2-fluorophenyl)-2-propyl>acetamide 
• 226411-05-8 N'-<1-(4-N-benzyl-N-methylamino-2-fluorophenyl)-2-propyl>-N,N-dibenzylglycinamide 
• 676628-04-9 6-[(3-fluoro-phenyl)-methyl-amino]-4-isopropyl-N-(tetrahydro-pyran-4-ylmethyl)-nicotinamide 
• 113734-41-1 N-methyl-N-p-fluorobenzyl-m-fluoroaniline 

Relevant academic research and scientific papers

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.

Selective N -monomethylation of primary anilines with the controllable installation of N -CH2D, N -CHD2, and N -CD3units

The selective N-monomethylation of primary anilines was realized by the use of the Me3N-BH3/N,N-dimethylformamide (DMF) system as the methyl source. This method also allows for the controllable introduction of N-CH2D, N-CHD2, and N-CD3 units with high lev

Selective mono-N-methylation of nitroarenes with methanol catalyzed by atomically dispersed NHC-Ir solid assemblies

A series of N-heterocyclic carbene-iridium (NHC-Ir) coordination assemblies based on bis-pyrenoimidazolium salts are prepared, and shown to function as efficient solid molecular catalysts in selective mono-N-methylation of nitroarenes with methanol under mild conditions. The atomically dispersed active Ir(I) centers and the large π-conjugation rings endow the solid catalysts with an exceptionally high activity and selectivity for a broad substrate scope. Such solid NHC-Ir coordination assemblies are robust, which can be easily recovered and reused more than 10 runs without significant loss of their catalytic activity and selectivity. When combined with a subsequent formylation using the same solid catalysts under ambient conditions, this novel protocol can afford diverse formamides in excellent yields, further highlighting the applicability of the present solid catalysts for an efficient diversification of nitroarenes to a broad number of functional amines.

Highly selective hydrogenation of amides catalysed by a molybdenum pincer complex: Scope and mechanism

A series of molybdenum pincer complexes has been shown for the first time to be active in the catalytic hydrogenation of amides. Among the tested catalysts, Mo-1a proved to be particularly well suited for the selective C-N hydrogenolysis of N-methylated formanilides. Notably, high chemoselectivity was observed in the presence of certain reducible groups including even other amides. The general catalytic performance as well as selectivity issues could be rationalized taking an anionic Mo(0) as the active species. The interplay between the amide CO reduction and the catalyst poisoning by primary amides accounts for the selective hydrogenation of N-methylated formanilides. The catalyst resting state was found to be a Mo-alkoxo complex formed by reaction with the alcohol product. This species plays two opposed roles-it facilitates the protolytic cleavage of the C-N bond but it encumbers the activation of hydrogen.

Rhodium(iii)-catalyzed indole synthesis at room temperature using the transient oxidizing directing group strategy

Rh-catalyzed reactions of N-alkyl anilines with internal alkynes at room temperature have been developed using an in situ generated N-nitroso group as a transient oxidizing directing group. Due to mild reaction conditions, this method enabled synthesis of a broad range of N-alkyl indoles, including even two indole-based medicinal compounds. Our work disclosed the feasibility of the transient oxidizing directing group strategy in C-H functionalization reactions, which possesses the potential to enhance overall step-economy and impart new reactivity patterns to substrates.

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.

Synthesis and Biological Evaluation of Selenium-Containing 4-Anilinoquinazoline Derivatives as Novel Antimitotic Agents

Twenty-eight novel selenium-containing 4-anilinoquinazoline derivatives were designed, synthesized, and evaluated as antiproliferative agents. Most of them had significant in vitro activities, particularly for compounds 23a, 25a, and 25d, which also exhibited the most potent antitumor activities against cisplatin-resistant cell lines and the doxorubicin-resistant cell lines, good selectivity toward normal cells, and obvious inhibitory effect on migration of A549 cell lines. Further mechanistic studies revealed that 23a, 25a, and 25d induce G2/M phase arrest and apoptosis in A549 cells, which was associated with a collapse of the mitochondrial membrane potential, alterations in the expression of some cell cycle-related and apoptosis-related proteins, and increasing the intracellular ROS level. Finally, compounds 23a, 25a, and 25d also effectively inhibited the tumor growth in the A549 xenograft model without obvious hints of toxicity. Taken together, these in vitro and in vivo results suggest that 23a, 25a, and 25d may be promising microtubule-stabilizing agents and can be used as a promising lead for the development of new antitumor agents.

Electronic effect of substituents on anilines favors 1,4-addition to: Trans -β-nitrostyrenes: Access to N -substituted 3-arylindoles and 3-arylindoles

A simple and an efficient method for the regioselective synthesis of N-alkyl/aryl/H 3-arylindole derivatives from N-substituted anilines and trans-β-nitrostyrenes has been described using 10 mol% of bismuth(iii) triflate as a catalyst in acetonitrile at 80 °C. The present protocol profits from the formation of new C-C and C-N bonds, broad substrate scope and moderate to good yields.

Towards Uniform Iodine Catalysis: Intramolecular C?H Amination of Arenes under Visible Light

A photochemical catalytic amination of arenes is presented. The reaction proceeds under benign iodine catalysis in the presence of visible light as the initiator and provides access to a range of differently substituted arylamines. A total of 29 examples demonstrate the broad applicability of this mild oxidation method. The scope of the reaction could further be expanded to silyl-tethered derivatives, which undergo intramolecular amination upon formation of seven-membered heterocycles. Cleavage of the silicon tether provides access to the corresponding 3-substituted anilines.