433-14-7

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
4-Fluoro-N-methylbenzenesulphonamide is utilized as a building block for the synthesis of potential antitumor and antimicrobial agents due to its unique structural features and reactivity. Its presence in these agents can contribute to enhanced therapeutic effects and selectivity against disease-causing organisms or tumor cells.
Used in Organic Synthesis:
In the field of organic synthesis, 4-Fluoro-N-methylbenzenesulphonamide is employed as a versatile intermediate. Its ability to participate in various chemical reactions allows for the creation of a wide range of organic compounds, expanding the scope of chemical libraries and potential applications.
Used in Medicinal Chemistry:
4-Fluoro-N-methylbenzenesulphonamide is used as a key component in the design and synthesis of new pharmaceuticals. Its incorporation into drug molecules can lead to improved pharmacokinetic and pharmacodynamic properties, such as better absorption, distribution, metabolism, and excretion profiles, as well as increased potency and selectivity.
Used as an Enzyme Inhibitor:
4-Fluoro-N-methylbenzenesulphonamide has shown promise as an inhibitor of certain enzymes. This application is significant in the development of drugs targeting specific enzymatic pathways involved in disease progression, offering a potential therapeutic strategy for various conditions.
Overall, 4-Fluoro-N-methylbenzenesulphonamide's multifaceted utility underscores its importance in the advancement of pharmaceuticals and organic chemistry, with ongoing research aimed at uncovering its full potential in therapeutic applications.

Upstream product

• 349-88-2 4-Fluorobenzenesulfonyl chloride 
• 74-89-5 methylamine 
• 824-75-9 p-fluorobenzamide 
• 67-56-1 methanol 
• 402-46-0 4-fluorophenylsulphonamide 
• 593-51-1 methylamine hydrochloride 
• 80-43-3 bis(1-methyl-1-phenylethyl)peroxide 

Downstream Products

• 287379-45-7 ethyl 4-[(4-fluorobenzenesulfonyl)methylamino]-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate 
• 117796-40-4 4-fluoro-N-methyl-N-(2-phenyl-2-propenyl)-benzenesulfonamide 
• 917761-25-2 4,4'-dithiobis-N-methylbenzenesulfonamide 
• 346692-36-2 N-benzyl-4-fluoro-N-methylbenzenesulfonamide 
• 1620220-76-9 C₁₁H₁₂FNO₃S 

Relevant academic research and scientific papers

Copper-catalyzed oxidative methylation of sulfonamides by dicumyl peroxide

A novel and facile copper-catalyzed methylation of sulfonamides was herein demonstrated. The practical transformation took place readily under the oxidative conditions, and N-methyl amides (23 examples) were successfully furnished in high efficiency (up to 90% yields). Dicumyl peroxide was considered to act not only as the oxidant in the system, but also methyl donor for the methylation protocol.

N-Methylation of Amines with Methanol in the Presence of Carbonate Salt Catalyzed by a Metal-Ligand Bifunctional Ruthenium Catalyst [(p-cymene)Ru(2,2′-bpyO)(H2O)]

A ruthenium complex [(p-cymene)Ru(2,2′-bpyO)(H2O)] was found to be a general and efficient catalyst for the N-methylation of amines with methanol in the presence of carbonate salt. Moreover, a series of sensitive substituents, such as nitro, ester, cyano, and vinyl groups, were tolerated under present conditions. It was confirmed that OH units in the ligand are crucial for the catalytic activity. Notably, this research exhibited the potential of metal-ligand bifunctional ruthenium catalysts for the hydrogen autotransfer process.

Recyclable covalent triazine framework-supported iridium catalyst for the N-methylation of amines with methanol in the presence of carbonate

An iridium complex Cp*Ir@CTF, which is synthesized by the coordinative immobilization of [Cp*IrCl2]2 on a functionalized covalent triazine framework (CTF), was found to be a general and highly efficient catalyst for the N-methylation of amines with methanol in the presence of carbonate. Under environmentally benign conditions, a variety of desirable products were obtained in high yields with complete selectivities and functional group friendliness. Furthermore, the synthesized catalyst could be recycled by simple filtration without obvious loss of catalytic activity after sixth cycle. Notably, this research exhibited the potential of covalent triazine framework-supported transition metal catalysts for hydrogen autotransfer process.

Direct Introduction of Sulfonamide Groups into Quinoxalin-2(1H)-ones by Cu-Catalyzed C3-H Functionalization

Direct sulfonamidation of quinoxalin-2(1H)-one derivatives has been developed using a readily available Cu salt as the catalyst and inexpensive ammonium persulfate as the oxidant in moderate conditions. Owing to the feature of handy operation and good functional group tolerance, this method provides a convenient and efficient access to curative 3-sulfonamidated quinoxalin-2(1H)-one scaffolds.

Method for synthesizing N-methyl sulfonamide in water

The invention discloses a method N - for synthesizing,methylsulfamide in water, by using a transition metal iridium catalyst to catalyze N - methylation reaction. by using a non-toxic and harmless water as a solvent, to avoid using the organic agent; to react only as a byproduct, without an environmental hazard; reaction temperature with respect to the previous strip more mild; and have a wide application prospect; with high selectivity, reaction atomic economy.

N-Methylation of Amines with Methanol in Aqueous Solution Catalyzed by a Water-Soluble Metal-Ligand Bifunctional Dinuclear Iridium Catalyst

The N-methylation of amines with methanol in aqueous solution was proposed and accomplished by using a water-soluble metal-ligand bifunctional dinuclear iridium catalyst. In the presence of [(Cp*IrCl)2(thbpym)][Cl]2 (1 mol %), a range of desirable products were obtained in high yields under environmentally benign conditions. Notably, this research exhibited the potential of transition metal-catalyzed activation of methanol as a C1 source for the construction of the C-N bond in aqueous solution.

Transition-Metal-Free One-Step Synthesis of Ynamides

A robust transition-metal-free one-step strategy for the synthesis of ynamides from sulfonamides and (Z)-1,2-dichloroalkenes or alkynyl chlorides is presented. This method is not only effective for internal ynamides but also amenable for terminal ynamides. Various functional groups, even the vinyl moiety, are compatible, and thus, this strategy offers the opportunity for further functionalization.

Copper(i)-catalyzed N-H olefination of sulfonamides for: N -sulfonyl enaminone synthesis

This communication reports copper-catalyzed N-H olefination of sulfonamides for enaminone synthesis using saturated ketones as olefin sources. With TEMPO derivatives and O2 as oxidants, this method provided an efficient way to produce various enaminones in good yields. Mechanistic studies helped figure out the stable intermediates and develop novel methodologies for the difunctionalization of saturated ketones.

Copper-Catalyzed Arylsulfonylation and Cyclizative Carbonation of N-(Arylsulfonyl)acrylamides Involving Desulfonative Arrangement toward Sulfonated Oxindoles

Sulfonated oxindoles are accessed by a Cu(OAc)2-catalyzed three-component reaction of N-(arylsulfonyl)acrylamides, DABSO, and aryldiazonium tetrafluoroborates. This transformation is triggered by the formation of arylsulfonyl radicals in situ from the reaction of aryldiazonium tetrafluoroborates and DABSO. Afterward, the sequential radical addition, radical cyclization, and desulfonylative 1,4-aryl migration take place to provide the final product by the formation of four new bonds in one pot. This procedure shows good functional group tolerance.

UV Light Induced Direct Synthesis of Phenanthrene Derivatives from a Linear 3-Aryl-N-(arylsulfonyl) Propiolamides

A novel photochemical approach for the synthesis of phenanthrene derivatives from linear 3-aryl-N-(arylsulfonyl) propiolamides via a tandem radical Smiles rearrangement/C-S bonding/Mallory reaction is disclosed. The control experiment results and isolation of the key intermediates give further insight into the reaction mechanism. Gram scale reaction using a flow reactor demonstrated the synthetic potential applications of our protocol.