312-52-7

Usage

Uses

Used in Pharmaceutical Synthesis:
4-Fluoro-N-phenyl-benzenesulfonamide is used as a key intermediate in the synthesis of pharmaceuticals for its significant pharmacological properties. It contributes to the development of drugs with anti-inflammatory and analgesic effects, making it instrumental in the creation of medications for pain relief and inflammation management.
Used in Agrochemical Production:
In the agrochemical industry, 4-Fluoro-N-phenyl-benzenesulfonamide is utilized as a crucial component in the production of various agrochemicals. Its role in this sector is vital for the development of effective and targeted pest control solutions, contributing to enhanced crop protection and yield.
Used in Dye and Pigment Manufacturing:
4-Fluoro-N-phenyl-benzenesulfonamide is employed as a vital ingredient in the manufacturing of dyes and pigments. Its unique chemical structure allows for the creation of a wide range of colors and shades, making it an essential component in the production of high-quality dyes and pigments for various applications, including textiles, plastics, and printing inks.
Used in Organic Synthesis Research:
As a versatile intermediate in organic synthesis, 4-Fluoro-N-phenyl-benzenesulfonamide is extensively used in research for the development of new chemical compounds and materials. Its unique properties and reactivity make it a valuable tool for exploring novel chemical reactions and synthesizing new organic compounds with potential applications in various industries.

InChI:InChI=1/C12H10FNO2S/c13-10-6-8-12(9-7-10)17(15,16)14-11-4-2-1-3-5-11/h1-9,14H

Upstream product

• 349-88-2 4-Fluorobenzenesulfonyl chloride 
• 62-53-3 aniline 
• 402-46-0 4-fluorophenylsulphonamide 
• 108-94-1 cyclohexanone 
• 824-80-6 sodium 4-fluorobenzenesulfinate 
• 98-95-3 nitrobenzene 
• 873-55-2 sodium benzenesulfonate 
• 3895-25-8 4-fluorophenylsulfonyl isocyanate 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 437-29-6 tris(4-fluorophenyl)bismuthane 
• 1765-93-1 4-fluoroboronic acid 
• 459-45-0 4-fluorobenzenediazonium tetrafluoroborate 
• 586-96-9 Nitrosobenzene 
• 920-66-1 1,1,1,3',3',3'-hexafluoro-propanol 

Downstream Products

• 106914-80-1 N-phenylmercuro-4-fluorobenzenesulfonanilide 
• 920011-98-9 N-{1-[2-(3-bromo-propoxy)-phenyl]-ethyl}-4-fluoro-N-phenyl-benzenesulfonamide 

Relevant academic research and scientific papers

Synthesis of N-phenylsulfonamide derivatives and investigation of some esterase enzymes inhibiting properties

In this study, synthesis of nine N-phenylsulfonamide derivatives was designed by starting from aniline, which is the simplest aromatic amine. These compounds were obtained in yields between 69 and 95%. Inhibitory properties of synthesized compounds on car

Copper-catalyzed synthesis of sulfonamides from nitroarenes: Via the insertion of sulfur dioxide

Nitroarenes are used as the coupling partners in the preparation of sulfonamides via the insertion of sulfur dioxide. A three-component reaction of arylboronic acids, nitroarenes, and potassium metabisulfite under copper catalysis proceeds smoothly, giving rise to a range of sulfonamides in good to excellent yields with broad substrate scope. Various functional groups including hydroxyl, cyano, amino, and carbonyl are all tolerated. A plausible mechanism is proposed, showing that arylsulfinate is the intermediate and the copper-assisted interaction of the nitroarene and arylsulfinate is the key step. This approach is also extended to the late-stage modification of a currently marketed drug (flutamide).

Sequential C-S and S-N Coupling Approach to Sulfonamides

A one-pot three-component reaction involving nitroarenes, (hetero)arylboronic acids, and potassium pyrosulfite leading to sulfonamides was described. A broad range of sulfonamides bearing different reactive functional groups were obtained in good to excellent yields through sequential C-S and S-N coupling that does not require metal catalysts.

Metal-free one-pot synthesis of N-arylsulfonamides from nitroarenes and sodium sulfinates in an aqueous medium

A metal-free one-pot two-step synthesis of sulfonamides from readily available nitroarenes and sodium arylsulfinates in a mixture of methanol and water has been developed. In this procedure, the aryl amines were produced in situ by the reduction of nitroarenes mediated by diboronic acid, and then coupled with sodium arylsulfinates in the presence of iodine. A series of N-arylsulfonamides with various functional groups were obtained in moderate to good yields under the optimal reaction conditions. In addition, this one-pot process is applicable for gram-scale synthesis.

Preparation method of sulfamide compound

The invention belongs to the technical field of organic chemistry, and particularly relates to a preparation method of a sulfamide compound, wherein the structure of the sulfamide compound synthesizedby the method is characterized and confirmed by H NMR and C NMR. The method comprises the following steps: in an organic solvent, carrying out a reaction on an aryl diazonium salt, a sulfur dioxide solid complex and an aryl nitroso compound in the presence of a reducing agent under a heating condition, wherein the diazonium salt and the sulfur dioxide solid complex act to generate aryl sulfonyl free radicals, and then the aryl nitroso compound is attacked; and reducing the generated hydroxylamine to obtain the sulfamide compound. The preparation method of the compound has the advantages of mild conditions, simplicity, high efficiency, no need of catalysts, no need of pre-synthesis of sulfonyl chloride or sodium sulfonate reagents, wide substrate application range, strong functionalgroup compatibility, convenience in separation and purification, and excellent industrial and medicinal chemical application values.

Method for coupling nitroaromatic compound and boric acid compound to synthesize sulfonamide compound

The invention belongs to the field of organic synthesis, and specifically discloses a method for coupling a nitroaromatic compound and a boric acid compound to synthesize a sulfonamide compound. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound comprises the steps that in an organic solvent, pyrosulfite is used as a source of SO2,and heating is carried out for a coupling reaction, and then after the post-treatment, the sulfonamide compound is obtained. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound is simple in operation, does not require nitrogen protection, and can be carried out under air. The nitroaromatic compound and the boric acid compound are abundant in source, relatively low in price, high in reaction yield, wide in applicability of a substrate and free in metal residual. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound can be used for synthesizing a series of sulfonamide compounds, and the synthesized compounds have wide application value in the fields of pesticidesand medicines.

Copper-catalyzed denitrogenative N-arylation of sulfoximines and sulfonamides with arylhydrazines

A Cu-mediated ligand-free arylation of NH-sulfoximines and sulfonamides by arylhydrazine hydrochlorides was herein demonstrated. The oxidative transformation provided an easy access towards N-aryl sulfoximines and sulfonamides in high yields (up to 93% yields) with broad functional groups tolerance (up to 36 examples). The protocol was proposed to take place through the free radical pathway based on the results of control reactions and EPR analysis.

Sulfonyl imide or sulfonamide of the denitrification arylation method and product and application

A sulfonyl imide or sulfonamide of the denitrification arylation method and product and application, sulfonimide or sulfonamide of the denitrification arylation method, comprises the following steps: to arylhydrazine and sulfonyl imide or sulfonamide as raw material, the catalyst palladium salt, alkali, solvent and oxidizing agent in the presence of, prepared N - aryl sulfonyl imide or N - aryl sulfonamides. The sulfonimide or sulfonamide of the denitrification arylation method, by adopting the arylhydrazine and sulfonimide or sulfonamide as raw materials used to prepare N - aryl sulfonyl imide or N - aryl sulfonamides, arylhydrazine because of having low cost, high reactivity and easy accessibility and the like, can make the sulfonyl imide or a sulfonamide for the arylation of the method cost is relatively low. The arylhydrazine as aryl group donor, the reaction by-product is N2 And H2 O, so it has the characteristics of green and environmental protection.

Multicomponent synthesis of sulfonamides from triarylbismuthines, nitro compounds and sodium metabisulfite in deep eutectic solvents

A sustainable synthesis of sulfonamides using a copper-catalysed process starting from triarylbismuthines, Na2S2O5 and nitro compounds in a Deep Eutectic Solvent (DES) as a reaction medium is described. Thus, triarylbismuthines are used as reagents for the incorporation of SO2 into organic motifs. The bismuth salts formed as by-products can be easily removed from the crude reaction mixture by precipitation with water, while the use of volatile organic compounds (VOCs) as solvents can be avoided in the entire process. The eutectic mixture employed as the solvent is fully characterised, with the preliminary results proving its low toxicity. The designed DES also allows for a novel multicomponent reaction which saves time and reduces purification steps, energy and cost.

Transition-metal-free synthesis of aromatic amines via the reaction of benzynes with isocyanates

An unexpected reaction between benzynes and isocyanates to generate aromatic amines has been developed under transition-metal-free conditions. The in situ prepared anions formed through cleavage of the N–C bond in isocyanates, reacted with aryne precursor