3695-00-9

Usage

Uses

Used in Pharmaceutical Industry:
DI-P-TOLUENESULFONAMIDE is used as a reagent for the preparation of carbonic anhydrase inhibitors with modified sulfonamido groups. These inhibitors play a crucial role in the development of drugs targeting various medical conditions, such as glaucoma, epilepsy, and altitude sickness, by regulating the activity of carbonic anhydrase enzymes.
The chemical properties of DI-P-TOLUENESULFONAMIDE, including its white crystalline powder form, make it a suitable candidate for use in the pharmaceutical industry, where it contributes to the synthesis of essential drugs for treating a range of health issues.

InChI:InChI=1/C14H15NO4S2/c1-11-3-7-13(8-4-11)20(16,17)15-21(18,19)14-9-5-12(2)6-10-14/h3-10,15H,1-2H3

Upstream product

• 70-55-3 toluene-4-sulfonamide 
• 98-59-9 p-toluenesulfonyl chloride 
• 536-57-2 p-toluene sulfinic acid 
• 127-65-1 chloroamine-T 
• 102238-22-2 O-Benzolsulfonyl-N,N-bis--hydroxylamin 
• 1153-45-3 4-nitrophenyl 4-methylbenzenesulfonate 
• 56410-24-3 N,N'-bis(p-toluenesulfonyl)hydroxylamine 
• 941-55-9 4-toluenesulfonyl azide 
• 824-79-3 sodium 4-methylbenzenesulfinate 

Downstream Products

• 84053-62-3 C₂₁H₂₆N₂O₄S₂ 
• 60852-10-0 N-chlorodi(p-tolylsulfonyl)amine 
• 84566-22-3 tetramethylbis[bis(p-tolylsulfonyl)amino]distannoxane 
• 1204779-03-2 C₅H₁₂N₂O*C₁₄H₁₅NO₄S₂ 
• 1257660-76-6 N-(2-(1,1-dioxido-3-oxobenzo[d]isothiazol-2(3H)-yl)hexyl)-4-methyl-N-tosylbenzenesulfonamide 
• 1257660-86-8 N-(1-bistosylamido-7-azido-hept-2-yl)saccharin 
• 1257660-80-2 N-(1-cyclohexyl-2-bistosylamido-ethyl)saccharin 
• 1257660-78-8 N-(2-(1,1-dioxido-3-oxobenzo[d]isothiazol-2(3H)-yl)dodecyl)-4-methyl-N-tosylbenzenesulfonamide 
• 1257660-88-0 N-(1-bistosylamido-4,4-bis(ethyloxycarbonyl)-but-2-yl)saccharin 
• 1257660-75-5 N-(2-(1,1-dioxido-3-oxobenzo[d]isothiazol-2(3H)-yl)octyl)-4-methyl-N-tosylbenzenesulfonamide 
• 1257660-77-7 N-(2-(1,1-dioxido-3-oxobenzo[d]isothiazol-2(3H)-yl)decyl)-4-methyl-N-tosylbenzenesulfonamide 
• 1257660-85-7 N-(1-bistosylamido-7-bromo-hept-2-yl)saccharin 
• 1257660-84-6 N-(1-bistosylamido-10-bromo-dec-2-yl)saccharin 
• 1257660-82-4 N-(1-bistosylamido-10-(methyloxycarbony)decan-2-yl)saccharin 

Relevant academic research and scientific papers

Merging Photoredox Catalysis with Transition Metal Catalysis: Direct C4-H Sulfamidation of 1-Naphthylamine Derivatives

A mild and efficient protocol for the copper(I)-catalyzed C4-H sulfamidation of 1-naphthylamine derivatives with diphenylsulfonimide (NHSI) was explored at room temperature, affording the desire produces in moderate to good yields. The control experiments indicated that this visible-light-promoted reaction might proceed via a single-electron-transfer process. In addition, preliminary DFT studies for the intermediates in the catalytic cycle were also explored, indicating that the C4 site in the naphthyl ring is the most likely electrophilic reactive site and providing some exact basis for the plausible mechanism.

Alkene Syn- And Anti-Oxyamination with Malonoyl Peroxides

Malonoyl peroxide 6 is an effective reagent for the syn- or anti-oxyamination of alkenes. Reaction of 6 and an alkene in the presence of O-tert-butyl-N-tosylcarbamate (R3 = CO2 tBu) leads to the anti-oxyaminated product in up to 99% yield. Use of O-methyl-N-tosyl carbamate (R3 = CO2Me) as the nitrogen nucleophile followed by treatment of the product with trifluoroacetic acid leads to the syn-oxyaminated product in up to 77% yield. Mechanisms consistent with the observed selectivities are proposed.

A Novel Synthesis of N -Sulfonylformamidines from N Sulfonyl sulfonamides

N -Sulfonylformamidines were synthesized from N -sulfonylsulfonamides by reacting with p -toluenesulfonyl chloride (TsCl) and N, N - disubstituted formamides. In this reaction, it was expected that mixing TsCl with the N, N -disubstituted formamide would generate an iminium salt (Vilsmeier reagent). The reaction avoids the use of metal catalysts and hazardous reagents, and the desired N -sulfonylformamidines were obtained in 60% to quantitative yields.

Hypervalent iodine(III)-Mediated oxidative decarboxylation of β,γ-unsaturated carboxylic acids

A novel oxidative decarboxylation of β,γ-unsaturated carboxylic acids mediated by hypervalent iodine(III) reagents is described. The decarboxylative C-O bond forming reaction proceeded in the presence of PhI(OAc)2 to give the corresponding allylic acetates. In addition, decarboxylative C-N bond formation was achieved by utilizing hypervalent iodine(III) reagents containing an I-N bond. Mechanistic studies suggest the unique reactivity of hypervalent iodine reagents in this ionic oxidative decarboxylation.

N-bromo-(4-methylphenyl) sulfonimide: A mild and efficient reagent for oxidative deoximation of oximes under microwave irradiations

Aldoximes and ketoximes are converted to the parent carbonyl compounds in good yields when treated with N-bromo-(4-methylphenyl) sulfonimide (2), under microwave irradiations. The simple work-up minimizes the loss of product and oximes have been selectively oxidized in the presence of alcohols and alkenes.

N-Bromobis(p-toluenesulfonyl)amine as a novel and mild reagent for conversion of oximes to carbonyl compound

N-Bromobis(p-toluenesulfonyl)amine (NBBTA) is a novel and efficient reagent for the conversion of oximes to their corresponding carbonyl compounds in good yields under mild conditions.

Interaction in molecular crystals, 162 [1, 2]. Di(arylsulfonyl)amines - Ligands for lipophilically wrapped polyion aggregates with Cs⊕-layers of variable thickness

Di(arylsulfonyl)amides are presented as novel anionic ligands for polycation aggregates. Starting from the structures of Ag⊕ and Na⊕ salts registered in the Cambridge Structural Database, the largest alkali cation Cs⊕ with high coordination number has been selected and in extreme low gradient crystallisation single crystals of both cesium-di(benzenesulfonyl)amide and cesium-di(4-toluenesulfonyl)amide were grown. Their structure determinations revealed that both polymeric salts contain cation layers (Cs⊕)∞: The one lipophilically wrapped by di(benzenesulfonyl)amide ligands exhibits hexagonal (Cs⊕)6 subunits, whereas the methyl-substituted di(4-toluenesulfonyl)amide ligands of the other one are interspersed within (Cs⊕)∞ layers. The resulting lipophilically wrapped sheets with Cs⊕ cations of ten- and twelve-fold coordination to disulfonyl O and C centers vary in their overall thickness of 1.77 nm and 1.39 nm because the toluene substituents in the thinner one are tilted. The remarkable effects caused by the 4-methyl substitution of the phenyl rings determine the structures of the parent di(arylsulfonyl)amines as well: Contrary to the polymeric phenyl substituted derivative, the toluene homologue crystallizes in dimers. The single crystals grown of the closely related di(arylsulfonyl)amides with or without para methyl substituents and their poly(Cs⊕) aggregates without any solvent inclusion show hitherto unknown structural motifs and, therefore, further improve our knowledge of alkali salt self-organisation phenomena in crystals.

Nucleophilic substitution at a four-coordinate sulfur atom. IV. Reactivity of anionic nitrogen-containing nucleopiles

The second-order rate constants for reactions of anions derived from azoles, arenesulfonamides, and arenesulfonohydrazides with aryl toluenesulfonates and methyl iodide in 5% aqueous ethanol (μ 1.0) at 25°C were compared with corresponding rate constants for aliphatic and heterocyclic amines. The kinetic behavior of neutral and anionic nitrogen-containing bases in reactions involving acyl (4-nitrophenyl acetate and 4-nitrophenyl heptanoate) and toluenesulfonyl group transfer suggests that deviation from the Bronsted dependence is due to unfavorable solvation effects for nucleophiles with pKa ≥ 11.0 rather than to change in the transition state structure. In reactions with a soft substrate, methyl iodide, solvation effects scarcely play the determining role, and the reduced reactivity of the anionic nucleophiles relative to neutral species is most likely to result from structural differences in the transition states corresponding to methyl group transfer to neutral and anionic nitrogen-containing compounds. The α-effect with arenesulfonohydrazides was revealed for the first time. 1996 MAEe Cyrillic signΚ Hayκa/Interperiodica Publishing.

Effects of medium and substituents on dissociation of 4,4′-disubstituted bis(benzenesulfon)imides

Ten 4,4′-disubstituted bis(arenesulfon)imides of the general formula XC6H4SO2NHSO2C6H 4X have been synthesized and their structures confirmed by their 1H NMR spectra. Elemental analyses are presented for the compounds not yet described. The dissociation constants of these model substances have been measured potentiometrically in pyridine, dimethylformamide, methanol, ethanol, propylene carbonate, acetone, acetonitrile, 1,2-dichloroethane and tetramethylene sulfone. The pKHA values obtained have been correlated with three sets of the Hammett substituent constants and the results have been used to discuss the solvent and substituent effects on the dissociation of the compounds studied. Sulfonimides with electron-acceptor substituents behave as rather strong acids in some solvents (pyridine, dimethylformamide, methanol and ethanol), whereas normal substituent dependences are found in other solvents. The experimental data have also been interpreted with the help of the statistical methods based on latent variables. From the calculations it follows that only the first principal component, which correlates well with the substituent constant sets adopted, is statistically significant in describing the substituent effect on the acid-base process studied.