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 
• 70717-27-0 1-[(4-methylphenyl)sulfonyl]-1H-azepine 
• 5504-03-0 N¹-tosyl-N¹,N²-diphenylacetamidine 
• 109774-61-0 tert-butyl phenyl(tosyl)carbamate 
• 138711-60-1 C₁₆H₁₇NOS 
• 75-03-6 ethyl iodide 
• 630-19-3 pivalaldehyde 
• 5504-03-0 4-Methyl-N-phenyl-N-{1-[(Z)-phenylimino]-ethyl}-benzenesulfonamide 
• 100-01-6 4-nitro-aniline 

Downstream Products

• 599-62-2 N-methyl-N-phenyltoluenesulfonamide 
• 124119-54-6 N,N'-butanediyl-bis-toluene-4-sulfonanilide 
• 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 
• 102011-03-0 4-[N-(toluene-4-sulfonyl)-anilino]-butyric acid ethyl ester 
• 104-23-4 4'-aminoazobenzene-4-sulfonic acid 
• 115486-65-2 N-dodecyl-toluene-4-sulfonanilide 
• 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 

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.

A facile and versatile electro-reductive system for hydrodefunctionalization under ambient conditions

A general electrochemical system for reductive hydrodefunctionalization is described, employing the inexpensive and easily available triethylamine (Et3N) as a sacrificial reductant. This protocol is characterized by facile operation, sustainable conditions, and exceptionally wide substrate scope covering the cleavage of C-halogen, N-S, N-C, O-S, O-C, C-C and C-N bonds. Notably, the selectivity and capability of reduction can be conveniently switched by simple incorporation or removal of an alcohol as a co-solvent.

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.

A new generation of terminal copper nitrenes and their application in aromatic C-H amination reactions

Copper nitrene complexes are highly reactive species and are known as intermediates in the copper catalyzed C-H amination. In this study, three novel copper tosyl nitrene complexes were synthesized at low temperatures, stabilized with heteroscorpionate ligands of the bis(pyrazolyl)methane family. The copper nitrenes were obtained by the reaction of a copper(i) acetonitrile complex with SPhINTs in dichloromethane. We show that the ligand design has a major influence on the catalytic activity and the thermal stability of the copper nitrene complex. Not only the choice of the third N donor, but also the substituent in the 5-position of the pyrazolyl moiety, have an impact on the stability. Furthermore, the novel copper nitrene complexes were used for catalytic aziridination of styrenes and C-H amination reactions of aromatic and aliphatic substrates under mild reaction conditions. Even challenging substrates like benzene and cyclohexane were aminated with good yields. The copper nitrene complexes were characterized using UV/Vis spectroscopy, low temperature Evans NMR spectroscopy, density functional theory, domain-based local pair natural orbital coupled cluster calculations (DLPNO-CCSD(T)) and cryo-UHR mass spectrometry.

Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides

A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazide with NXS (X = Cl or Br) and late-stage conversion to several other functional groups was described. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides and sulfonates. In most cases, these reactions are highly selective, simple, and clean, affording products at excellent yields.

Immobilization of copper(II) into polyacrylonitrile fiber toward efficient and recyclable catalyst in Chan-Lam coupling reactions

A series of polyacrylonitrile fiber (PANF)-supported copper(II) catalysts were prepared through the immobilization of Cu(II) into prolinamide-modified PANF (PANPA-2F) and subsequently used for the synthesis of diverse N-arylimidazoles from arylboronic acids and imidazole. The prepared Cu(II)@PANPA-2Fs were well characterized by mechanical strength, FT-IR, XRD, XPS and SEM. Among them, CuCl2@PANPA-2F exhibited excellent catalytic performance, and its activity was significantly affected by the Cu loading. This catalytic system also displayed good activity in the synthesis of N-arylsulfonamides from arylboronic acids and tosyl azide. It was highly efficient in gram-scale reactions and could be reused five times. The advantages of low cost, easy preparation, good durability and facile recovery make the fiber catalyst attractive.