6380-05-8

Usage

Uses

Used in Pharmaceutical Industry:
N-(2-Chlorophenyl)-p-toluenesulfonamide is used as an intermediate in the synthesis of various pharmaceuticals, contributing to the development of new drugs and medicines.
Used in Pesticide Industry:
N-(2-Chlorophenyl)-p-toluenesulfonamide is utilized as an intermediate in the production of pesticides, providing a means to control and manage pests in agricultural settings.
Used in Dye Industry:
N-(2-Chlorophenyl)-p-toluenesulfonamide is used as an intermediate in the synthesis of dyes, playing a role in the creation of colorants for various applications.
Used in Microbiology:
Due to its antimicrobial and antifungal properties, N-(2-Chlorophenyl)-p-toluenesulfonamide is used in various industries for its broad-spectrum activity against a wide range of microorganisms, helping to prevent microbial contamination and growth.
Used in Organometallic Chemistry:
As a reagent, N-(2-Chlorophenyl)-p-toluenesulfonamide is employed in organometallic chemistry, facilitating specific chemical reactions and processes.
Used in Rubber Chemical Industry:
N-(2-Chlorophenyl)-p-toluenesulfonamide is utilized in the manufacture of rubber chemicals, contributing to the production of various rubber-based products.
Used in Petroleum Industry:
N-(2-Chlorophenyl)-p-toluenesulfonamide serves as a corrosion inhibitor in the petroleum industry, helping to protect equipment and infrastructure from the damaging effects of corrosion.

InChI:InChI=1/C15H17BrN2O3S/c1-4-21-14(19)12-8(2)17-15(22)18-13(12)10-7-9(20-3)5-6-11(10)16/h5-7,13H,4H2,1-3H3,(H2,17,18,22)

Upstream product

• 95-51-2 o-chloroaniline 
• 98-59-9 p-toluenesulfonyl chloride 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 108-90-7 chlorobenzene 
• 615-41-8 2-iodochlorobenzene 
• 70-55-3 toluene-4-sulfonamide 
• 106-45-6 para-thiocresol 
• 3900-89-8 2-Chlorobenzeneboronic acid 
• 68-34-8 phenyl toluenesulfonamide 
• 88-73-3 2-Chloronitrobenzene 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 103-19-5 di(p-tolyl) disulfide 

Downstream Products

• 1213-33-8 o-aminophenyl p-tolyl sulfone 
• 95-51-2 o-chloroaniline 
• 620604-38-8 4-(4-methylphenylsulphonyl)-2-chloroaniline 
• 135190-00-0 2,3-diphenyl-1-(p-toluenesulfonyl)indole 
• 1620787-21-4 N-(2-chloro-6-nitrophenyl)-4-methylbenzenesulfonamide 
• 7230-61-7 N-(2-chloro-4-nitrophenyl)-4-methylbenzenesulfonamide 
• 442155-91-1 4-methyl-N-{2-(phenylethynyl)phenyl}benzenesulfonamide 
• 107734-06-5 N-tosyl-2-phenylindole 
• 301359-12-6 N-(2,4-dichlorophenyl)-4-methylbenzenesulfonamide 
• 6625-10-1 C₁₃H₁₀Cl₃NO₂S 
• 121-87-9 2-Chloro-4-nitroaniline 
• 836610-99-2 4-nitro-2-(toluene-4-sulfonyl)-benzonitrile 

Relevant academic research and scientific papers

Ligand-Controlled Regiodivergence for Catalytic Stereoselective Semireduction of Allenamides

Ligand-controlled regiodivergence has been developed for catalytic semireduction of allenamides with excellent chemo- and stereocontrol. This system also provides an example of catalytic regiodivergent semireduction of allenes for the first time. The divergence of the semireduction is enabled by ligand switch with the same palladium pre-catalyst under operationally simple and mild conditions. Monodentate ligand XPhos exclusively promotes selective 1,2-semireduction to afford allylic amides, while bidentate ligand BINAP completely switched the regioselectivity to 2,3-semireduction, producing (E)-enamide derivatives.

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.

Differentiation of isomeric haloanilines by tosylation in combination with electrospray ionization mass spectrometry

Differentiation of the isomeric haloanilines still remains a challenging and?necessary?analytic task due to their identical retention time in chromatography and similar mass spectra. In this work, p-tosylation of haloanilines by reaction of haloanilines with p-toluenesulfonyl chloride resulted in the corresponding N-tosyl haloanilines. Fragmentation of protonated N-tosyl haloanilines in electrospray ionization tandem mass spectrometry (ESI-MS/MS) mainly resulted in tosyl cation, haloaniline radical cation, and halohydroxyaniline radical cation. The MS/MS of the three group isomeric derivatives showed significant difference in abundance distribution of these product ions, respectively. Theoretical calculations showed that the stability of the ion-neutral complex (INC) is a key factor influencing the relative intensity of the product ions. The three group isomeric derivatives were also separated by high performance liquid chromatograph (HPLC) at conventional conditions. p-Tosylation combined tandem MS (or HPLC) technique were carried out to realize the differentiation of isomeric haloanilines.

Revisiting 1-chloro-1,2-benziodoxol-3-one: Efficient: ortho -chlorination of aryls under aqueous conditions

The application of 1-chloro-1,2-benziodoxol-3-one as a powerful chlorinating agent as well as oxidant for aniline derivatives is explored. The amide directing group assisted radical mediated ortho-selective chlorination proceeds in the absence of a radical initiator. Various electronically differentiated anilides and sulfonamides are tolerated under aqueous conditions.

Synthesis of: N -arylsulfonamides via Fe-promoted reaction of sulfonyl halides with nitroarenes in an aqueous medium

A fascinating Fe-promoted protocol for the synthesis of N-arylsulfonamides has been developed. Starting from commercially available nitroarenes and sulfonyl chlorides, moderate to excellent yields of the corresponding N-arylsulfonamides can be obtained. In particular, Fe dust serves as the sole reductant in the transformation and it can be easily performed on a large scale.

Discovery, Optimization, and Biological Evaluation of Sulfonamidoacetamides as an Inducer of Axon Regeneration

Axon regeneration after injury in the central nervous system is hampered in part because if an age-dependent decline in the intrinsic axon growth potential, and one of the strategies to stimulate axon growth in injured neurons involves pharmacological manipulation of implicated signaling pathways. Here we report phenotypic cell-based screen of chemical libraries and structure-activity-guided optimization that resulted in the identification of compound 7p which promotes neurite outgrowth of cultured primary neurons derived from the hippocampus, cerebral cortex, and retina. In an animal model of optic nerve injury, compound 7p was shown to induce growth of GAP-43 positive axons, indicating that the in vitro neurite outgrowth activity of compound 7p translates into stimulation of axon regeneration in vivo. Further optimization of compound 7p and elucidation of the mechanisms by which it elicits axon regeneration in vivo will provide a rational basis for future efforts to enhance treatment strategies.

Palladium-catalyzed N-arylsulfonamide formation from arylsulfonyl hydrazides and nitroarenes

A palladium-catalyzed construction for N-arylsulfonamide from nitroarenes and arylsulfonyl hydrazides is developed. In this protocol, abundant and stable nitroarenes serve as the nitrogen sources by in situ reduction reaction of hydrogen released from arylsulfonyl hydrazides. No external oxidants or reductants are needed for this kind of transformation.

Highly ortho-Selective Chlorination of Anilines Using a Secondary Ammonium Salt Organocatalyst

An organocatalytic, highly facile, efficient, and regioselective ortho-chlorination of anilines is described. A secondary ammonium chloride salt has been employed as the catalyst and the reaction can be conducted at room temperature without protection from air and moisture. In addition, the reaction is readily scalable and the catalyst can be recycled and reused. This catalytic protocol has been applied to the efficient synthesis of a highly potent c-Met kinase inhibitor. Mechanistic studies revealed that unique structural features of the secondary ammonium chloride salt are important for both the catalysis and regioselectivity of the electrophilic ortho-chlorination.

A convenient and benign synthesis of sulphonamides in PEG-400

A simple and convenient method is reported for the synthesis of a series of sulphonamides in PEG-400 using potassium carbonate as the base. The reaction is carried out in a heterogeneous medium and consequently product recovery is simple. The desired products with a variety of aromatic amines could be synthesized in a short reaction time in good yield. The PEG could be recovered for reuse.

Ultrasound-promoted green approach for the synthesis of sulfonamides using natural, stable and reusable Natrolite nanozeolite catalyst at room temperature

Natural Natrolite nanozeolite has been investigated as an efficient and reusable catalyst for the N-sulfonylation of amines under ultrasound irradiation at room temperature. Compared with traditional methods, the significant advantages for method are green solvent, milder and cleaner conditions, higher purity and yields, shorter reaction time, easier work-up procedure and the lower generation of waste or pollutions. The catalyst can be recovered and reused several times without significant loss of its catalytic activity.