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.

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.

N-Aroylsulfonamide-Photofragmentation (ASAP)-A Versatile Route to Biaryls

The photochemical fragmentation of N-aroylsulfonamides 9 (ASAP) is a powerful method for the preparation of various biaryls. Compounds 9 are easily accessible in two steps from amines by treatment with arenesulfonyl chlorides and aroyl chlorides. Many of these compounds were prepared for the first time. The irradiation takes place in a previously developed continuous-flow reactor using inexpensive UVB or UVC fluorescent lamps. Isocyanates and sulphur dioxide are formed as the only by-products. The ASAP tolerates a variety of functional groups and is even suited for the preparation of phenylnaphthalenes and terphenyls. The ASAP mechanism was elucidated by interaction of photophysical and quantum chemical (DFT) methods and revealed a spirocyclic biradical as key intermediate.

Recurrent Approximation of Retention Parameters of N-Substituted p-Toluenesulfonamides in Reversed-Phase High Performance Liquid Chromatography for Revealing the Formation of Their Hydrates

Abstract: Recurrent approximation of retention times in reversed-phase high performance liquid chromatography (RP-HPLC), tR(C + ΔC) = atR(C) + b, where C is the acetonitrile concentration in the eluent, and ΔC is the constant “step” of its variation, for six specially synthesized N-substituted p-toluenesulfonamides confirmed the presence of anomalies previously revealed for some complex polyfunctional organic compounds. The reason for these anomalies is the presence of sulfonamide –SO2–NH fragments in the molecules, which leads to hydration of sorbates in aqueous solutions, or, more precisely, to a change in the ratio of their non-hydrated and hydrated forms because of a shift in the equilibrium Х + Н2О $$ rightleftarrows $$ Х·Н2О (*) as a result of a change in the eluent composition. The same effect is indicated by the strong antibatic dependence of the retention indices RI(C) of all sulfonamides under study; the coefficients dRI/dC vary from –1.9 to –4.0, these values being much higher in magnitude than for compounds that do not form hydrates. Further independent evidence in favor of the transformation of sorbates due to variation of the eluent composition is the dependence of the relative absorbance Arel = A(254)/A(220) on the acetonitrile content in the eluent. This suggests changes in the chemical nature of chromophores in sulfonamide molecules depending on the equilibrium state (*).

Copper-Catalyzed Aminoarylation of Alkenes via Aminyl Radical Addition and Aryl Migration

We describe a new strategy for aminoarylation of alkenes by copper-catalyzed smiles rearrangement using O-benzoylhydroxylamines as the amine reagent. This method affords various β-amino amide derivatives possessing a quaternary carbon center with wide functional group tolerance and high regioselectivity. The mechanistic studies indicate that the transformation can involve aminyl radical intermediates under acid-free condition.