68-34-8

Usage

Uses

Used in Pharmaceutical Industry:
P-Toluenesulfonanilide is used as a reagent in the synthesis of new alkynyl-gold(I) complexes, which exhibit anti-cancer activity towards several cancer cell lines, such as HT29, IGROV1, HL60, and I407.
Used in Chemical Industry:
P-Toluenesulfonanilide is used as a reagent in the synthesis of α,β-unsaturated N-sulfonyl imides via the oxidation of sulfonyl ynamides catalyzed by zinc catalysts.
Used in Textile Industry:
P-Toluenesulfonanilide is used as a softener for acetylcellulose in proportions up to 50%.
Used in Dye Industry:
P-Toluenesulfonanilide is used as a dyestuff intermediate.

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

Upstream product

• 734-25-8 N-(4-nitrophenyl)-4-methylbenzenesulfonamide 
• 142-04-1 aniline hydrochloride 
• 55305-43-6 N-cyano-N-phenyl-p-toluenesulfonamide 
• 108-24-7 acetic anhydride 
• 62-53-3 aniline 
• 98-59-9 p-toluenesulfonyl chloride 
• 138711-60-1 C₁₆H₁₇NOS 
• 75-03-6 ethyl iodide 
• 630-19-3 pivalaldehyde 
• 54856-34-7 C₁₄H₁₉N₃O₃S 
• 102276-49-3 4-Methylbenzolsulfonsaeure-<1-phenyl-2-(phenylmethylen)>hydrazid 
• 941-55-9 4-toluenesulfonyl azide 
• 71-43-2 benzene 
• 75732-31-9 N-(p-methylbenzenesulfonyl)-N,O-bis(trimethylsilyl)hydroxylamine 

Downstream Products

• 108975-51-5 N-butyl-4-methyl-N-phenylbenzenesulfonamide 
• 65148-06-3 N-((4-methylphenyl)sulfonyl)-N-phenyl-beta-alanine 
• 1109-54-2 N,N'-methanediyl-bis-toluene-4-sulfonanilide 
• 1821-40-5 N-ethyl-toluene-4-sulfonanilide 
• 101582-56-3 N-sec-butyl-toluene-4-sulfonanilide 
• 104-23-4 4'-aminoazobenzene-4-sulfonic acid 
• 115486-65-2 N-dodecyl-toluene-4-sulfonanilide 
• 599-62-2 N-methyl-N-phenyltoluenesulfonamide 
• 734-25-8 N-(4-nitrophenyl)-4-methylbenzenesulfonamide 
• 2903-38-0 N-chloro-N-phenyl-toluene-4-sulfonamide 
• 6314-72-3 4-(N-phenyl)sulfamoylbenzoic acid 
• 301359-12-6 N-(2,4-dichlorophenyl)-4-methylbenzenesulfonamide 
• 36965-50-1 2-nitro-toluene-4-sulfonic acid-(2,4-dinitro-anilide) 
• 856352-69-7 toluene-4-sulfonic acid-(2,4,N-trichloro-anilide) 

Relevant academic research and scientific papers

Intermolecular iodofunctionalization of allenamides with indoles, pyrroles, and furans: Synthesis of iodine-substituted: Z -enamides

A new method was developed to synthesize iodine-substituted Z-enamides through N-iodosuccinimide-mediated intermolecular iodofunctionalization of allenamides with indoles, pyrroles, and furans. These reactions proceed rapidly and tolerate a broad scope of substrates. The conjugated sulfimide ion species probably acts as the key intermediate.

NIS-Mediated intermolecular hydroamination of allenamides with imidazole heterocycles: A facile protocol for the synthesis of allylic: N, N -acetals

Allylic N,N-acetals are important intermediates in the synthesis of biologically active heterocycles and natural products. Herein, we report a facile protocol for the synthesis of this compound through N-iodosuccinimide-mediated hydroamination of allenamides by imidazole heterocycles. The reaction is regioselective, fast, and tolerant of a broad scope of imidazole and benzimidazole derivatives. The key intermediate is a conjugated sulfimide ion species that undergoes nucleophilic attack by imidazole to form the 1,2-adduct. Mixtures of N1- and N3-substituted isomers were obtained using asymmetrically substituted imidazoles. However, the 1,4-adduct was obtained using a tri-substituted imidazole. The efficiency of the gram-scale reaction suggests the potential industrial application of this synthetic method.

Pressure-induced Synthesis of an N-Sulphonyl-1H-azepine by Sulphonyl-nitrene Insertion into Benzene

The thermal decomposition of toluene-p-sulphonyl azide (1) in an excess of benzene under a nitrogen atmosphere gave p-tosyl-1H-azepine (2), the yield of which increased with an increase in N2 pressure.

Lewis Acid Regulated Divergent Catalytic Reaction between Quinone Imine Ketals (QIKs) and 1,3-Dicarbonyl Compounds: Switchable Access to Multiple Products Including 2-Aryl-1,3-Dicarbonyl Compounds, Indoles, and Benzofurans

A catalytic Lewis acid regulated reaction between quinone imine ketals (QIKs) and 1,3-dicarbonyl compounds provides a divergent and tunable approach to a variety of skeletons, including a series of 2-aryl-1,3-dicarbonyl compounds, indoles, and benzofurans. The use of lithium chloride and ferrous bromide gives C3- or C2-alkylation products of the QIKs. The combination of ferrous bromide and trifluoromethanesulfonic acid delivers indole derivatives. Sequential hydrolysis and C3-alkylation occur in the presence of ytterbium (III) trifluoromethanesulfonate and stoichiometric amounts of water. When the reaction is performed with trifluoromethanesulfonic acid and stoichiometric amounts of water, benzofuran is obtained. This protocol utilizes mild conditions, exhibits regio- and chemoselectivity, and has broad functional group tolerance. (Figure presented.).

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.

Synthesis of magnetic chitosan supported metformin-Cu(II) complex as a recyclable catalyst for N-arylation of primary sulfonamides

The application of chitosan, which has received much attention as a natural polymer and effective support, has many advantages such as biodegradability and biocompatibility. In this study, the immobilization of a copper complex on the magnetic chitosan bearing metformin ligand has been developed through immobilizing structurally defined metformin with long tail of (3-chloropropyl)trimethoxysilane (TMOS). The synthesized Fe3O4-chitosan@metformin-Cu(II) complex (Fe3O4-CS@Met-Cu(II)) was used as an effective, reusable and magnetic catalyst in the N-arylation of different derivatives of primary sulfonamides with arylboronic acids in ethanol. The primary sulfonamides were prepared from the reaction of sulfonyl chlorides with sodium cyanate in water under ultrasonic irradiation. Utilizing a wide variety of substrates in EtOH as a green solvent, high yields of the primary and secondary sulfonamides, easy work-up along with the excellent recovery and reusability of the catalyst, make this process a simple, economic and environmentally benign method. The synthesized Fe3O4-CS@Met-Cu(II) was characterized using various techniques such as XRD (X-ray diffraction), EDS (energy-dispersive X-ray spectroscopy), elemental mapping, TEM (transmission electron microscopy), FESEM (field emission scanning electron microscopy), VSM (vibrating sample magnetometer), ICP-MS (inductively coupled plasma mass spectroscopy), TGA (thermogravimetric analysis) and FT-IR (Fourier-transform infrared spectroscopy) analyses. The catalyst can be recycled and reused 5 times with no considerable loss of catalytic activity.

A ligand-free copper-catalyzed strategy to the N-arylation of indazole using aryl bromides

A simple and efficient strategy for the C–N cross-coupling of indazole with a variety of substituted aryl bromides is reported. Under the optimized conditions, a broad scope of N-arylated products were obtained in good to excellent yields (up to 87%) under the ligand-free conditions.

Nickel-Catalyzed Reductive Cross-Coupling of N-Acyl and N-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides

Herein we report a Ni-catalyzed reductive transamidation of conveniently available N-acyl benzotriazoles with alkyl, alkenyl, and aryl nitro compounds, which afforded various amides with good yields and a broad substrate scope. The same catalytic reaction conditions were also applicable for N-sulfonyl benzotriazoles, which could undergo smooth reductive coupling with nitroarenes and nitroalkanes to afford the corresponding sulfonamides.

Nickel-Catalyzed C(sp3)-H Functionalization of Benzyl Nitriles: Direct Michael Addition to Terminal Vinyl Ketones

An efficient nickel(0)-catalyzed addition of benzyl nitriles to terminal vinyl ketones via C(sp3)-H functionalization has been developed. The reaction provides a novel and efficient protocol for the synthesis of α-functionalized benzyl nitriles with a wide range of structural diversity under mild reaction conditions while obviating the use of a strong base. The work might be potentially useful toward the development of an enantioselective variant using chiral nitrogen ligands.

A Strategy for Amide C-N Bond Activation with Ruthenium Catalyst: Selective Aromatic Acylation

A strategy for amide C-N bond activation with ruthenium catalyst is described for the first time. The in situ formed bis-cycloruthenated complexes were demonstrated to be the key active species with superior oxidative addition ability to an inert amide C-N bond. The direct C-H bond activation of 2-arylpyridines followed by the amide C-N bond activation took place in the presence of a ruthenium precatalyst to produce monoacylation products in moderate to good yields. Synthetically useful functional groups, such as halogen atoms (F and Cl), ester, acetyl, and vinyl, remained intact during tandem C-H/C-N bond activation reactions.