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Usage

Uses

Used in Polymer Manufacturing:
N-(o-tolyl)benzenesulphonamide is utilized as a plasticizer in the production of polymer products, such as polyvinyl chloride (PVC) and polyurethane. It enhances the flexibility and workability of these materials, contributing to their improved performance and durability.
Used in Chemical Production:
N-(o-tolyl)benzenesulphonamide serves as an intermediate in the synthesis of dyes, pharmaceuticals, and other organic compounds. Its role in these processes is crucial for the development of a range of products that have diverse applications across different industries.
Used in Various Industries:
Due to its versatility and low toxicity, N-(o-tolyl)benzenesulphonamide is employed across a spectrum of industries, including but not limited to plastics, pharmaceuticals, and dyes. Its applications are tailored to meet the specific requirements of each industry, leveraging its unique properties to achieve desired outcomes.
It is important to handle N-(o-tolyl)benzenesulphonamide with care and in compliance with safety regulations to ensure the safety of both the environment and the individuals involved in its use.

InChI:InChI=1/C13H13NO2S/c1-11-7-5-6-10-13(11)14-17(15,16)12-8-3-2-4-9-12/h2-10,14H,1H3

Upstream product

• 64-17-5 ethanol 
• 98-09-9 benzenesulfonyl chloride 
• 95-53-4 o-toluidine 
• 938-10-3 phenylsulfonyl azide 
• 108-88-3 toluene 
• 98-10-2 benzenesulfonamide 
• 615-37-2 ortho-methylphenyl iodide 
• 873-55-2 sodium benzenesulfonate 
• 635-26-7 o-tolylhydrazine hydrochloride 
• 88-72-2 1-methyl-2-nitrobenzene 
• 98-80-6 phenylboronic acid 
• 15898-37-0 sodium 2-methylbenzenesulfinate 
• 95-46-5 2-methylphenyl bromide 

Downstream Products

• 95793-70-7 N-Methyl-N-(2-methylphenyl)benzolsulfonamid 
• 1678-25-7 N-phenylbenzenesulfonamide 
• 54129-03-2 C₆H₅HgN(SO₂C₆H₅)C₆H₄CH₃ 
• 312-63-0 N-(4-fluorophenyl)benzenesulfonamide 
• 17359-41-0 benzoic acid-(N-benzyl-o-toluidide) 
• 853789-89-6 benzenesulfonic acid-(4-anilino-2,3-dichloro-6-methyl-anilide) 
• 117309-36-1 N-benzenesulfonyl-N-o-tolyl-glycine 

Relevant academic research and scientific papers

Deconstructing Noncovalent Kelch-like ECH-Associated Protein 1 (Keap1) Inhibitors into Fragments to Reconstruct New Potent Compounds

Targeting the protein-protein interaction (PPI) between nuclear factor erythroid 2-related factor 2 (Nrf2) and Kelch-like ECH-associated protein 1 (Keap1) is a potential therapeutic strategy to control diseases involving oxidative stress. Here, six classes of known small-molecule Keap1-Nrf2 PPI inhibitors were dissected into 77 fragments in a fragment-based deconstruction reconstruction (FBDR) study and tested in four orthogonal assays. This gave 17 fragment hits of which six were shown by X-ray crystallography to bind in the Keap1 Kelch binding pocket. Two hits were merged into compound 8 with a 220-380-fold stronger affinity (Ki = 16 μM) relative to the parent fragments. Systematic optimization resulted in several novel analogues with Ki values of 0.04-0.5 μM, binding modes determined by X-ray crystallography, and enhanced microsomal stability. This demonstrates how FBDR can be used to find new fragment hits, elucidate important ligand-protein interactions, and identify new potent inhibitors of the Keap1-Nrf2 PPI.

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.

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.

Characteristic Hydrogen Bonding Observed in the Crystals of Aromatic Sulfonamides: 1D Chain Assembly of Molecules and Chiral Discrimination on Crystallization

N-Phenylbenzenesulfonamides exist preferentially in (+)- or (-)-synclinal conformations, which place the aromatic rings at both ends in the same direction with a twist. We have systematically analyzed the crystal structure of secondary aromatic sulfonamides bearing methyl, ethyl, and/or methoxy groups on the benzene rings. Intermolecular hydrogen bonding between the sulfonamide protons and sulfonyl oxygens was observed in 81 out of 85 crystals. The intermolecular hydrogen-bonding patterns could be classified into four types, i.e. Dimeric, Zigzag, Helical, and Straight patterns, with retention of the synclinal conformation of the sulfonamide moiety. We investigated the relationship between the hydrogen-bonding pattern and the proportion of the compounds that show chiral crystallization. On the basis of our classification of the intermolecular hydrogen bonds of aromatic sulfonamides, the crystals with Dimeric and Zigzag patterns, which both have enantiomeric synclinal conformers, intrinsically become achiral, except for kryptoracemates. In contrast, a high proportion of compounds with Helical or Straight patterns in the crystals showed chiral crystallization. Our classification is useful for discussion regarding the chirality of molecular assemblies, on the basis of the conformational chirality of the molecules in the crystal.

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.

Palladium-catalyzed desulfitative arylation of sulfonamides with sodium arylsulfinates

A Pd(II)-catalyzed desulfitative arylation protocol between sulfonamides and sodium arylsulfinates was herein reported. The direct arylation reaction was successfully achieved by a Pd(II)/Ag(I)-mediated system without participation of any external ligands with a release of SO2. And different N-aryl sulfonamides were obtained readily in up to 86% yields, exhibiting good functional groups tolerance (25 examples).

Selective cleavage of the N-propargyl group from sulfonamides and amides under ruthenium catalysis

The selective cleavage of the N-propargyl group from sulfonamides and amides under ruthenium catalysis is described. The reaction tolerates a broad range of functional groups, and the desired products were obtained in 10–95% yield.

Sulfonamidation of Aryl and Heteroaryl Halides through Photosensitized Nickel Catalysis

Herein we report a highly efficient method for nickel-catalyzed C?N bond formation between sulfonamides and aryl electrophiles. This technology provides generic access to a broad range of N-aryl and N-heteroaryl sulfonamide motifs, which are widely represented in drug discovery. Initial mechanistic studies suggest an energy-transfer mechanism wherein C?N bond reductive elimination occurs from a triplet excited NiII complex. Late-stage sulfonamidation in the synthesis of a pharmacologically relevant structure is also demonstrated.

Visible Light-Induced Radical Rearrangement to Construct C-C Bonds via an Intramolecular Aryl Migration/Desulfonylation Process

A highly efficient intramolecular selective aryl migration/desulfonylation of 2-bromo-N-aryl-N-(arenesulfonyl)amide via visible light-induced photoredox catalysis has been accomplished. This approach allows for the construction of a variety of multisubstituted N,2-diarylacetamide under mild reaction conditions.

Sulfonamide formation from sodium sulfinates and amines or ammonia under metal-free conditions at ambient temperature

A novel, practical and highly efficient method for the construction of a variety of sulfonamides mediated by I2 was demonstrated. The reaction proceeds readily at room temperature using a variety of sodium sulfinates and amines or ammonia in water in a metal-, base-, ligand-, or additive-free protocol. Primary, secondary and tertiary sulfonamides were obtained in good to excellent yields with a broad range of functional group tolerability. This journal is