36744-90-8

Usage

Uses

Used in Pharmaceutical Industry:
S,S-DIPHENYLSULFILIMINE is used as an intermediate in the synthesis of various pharmaceuticals. Its unique chemical structure allows it to be a key component in the development of new drugs, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, S,S-DIPHENYLSULFILIMINE is also utilized as an intermediate. It plays a crucial role in the production of pesticides and other agrochemicals, helping to improve agricultural yields and protect crops from pests and diseases.
Given the compound's properties and applications, it is essential to manage its use and disposal with strict adherence to safety and environmental regulations to minimize potential hazards.

InChI:InChI=1/C12H11NS/c13-14(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,13H

Upstream product

• 32133-82-7 Martins sulfurane 
• 13150-76-0 N-[(4-methylphenyl)sulfonyl]-S,S-diphenyl-sulfilimine 
• 67-56-1 methanol 
• 42787-35-9 S,S-Diphenyl-N-iodosulfilimine 
• 40560-80-3 N-(diphenyl-λ⁴-sulfanylidene)benzenesulfonamide 
• 139-66-2 diphenyl sulfide 
• 64-17-5 ethanol 
• 42787-34-8 S,S-Diphenyl-N_.bromosulfilimine 
• 212077-68-4 S,S-diphenyl-S-[1,1-2H₂]propoxythiazyne 
• 67248-39-9 fluoro(diphenyl)-λ⁶-sulfanenitrile 
• 42787-33-7 S,S-Diphenyl-N-chlorosulfilimine 
• 87446-53-5 S,S-diphenyl-N-(trifluoroacetyl)sulfilimine 
• 143885-02-3 propyloxy(diphenyl)-λ⁶-sulfanenitrile 
• 143885-03-4 isopropyloxy(diphenyl)-λ⁶-sulfanenitrile 

Downstream Products

• 58463-67-5 C₁₆H₁₅NO₂S 
• 58463-66-4 C₁₇H₁₉NO₂S 
• 58485-81-7 C₁₆H₁₅NO₃S 
• 58463-63-1 C₂₀H₁₅NO₃S 
• 42397-54-6 N-(2',2'-Dicyanovinyl)-diphenylsulfilimin 
• 42397-56-8 N-(1',2',2'-Tricyanovinyl)-diphenylsulfilimin 
• 58940-90-2 S,S-diphenyl-N-(2-(phenylsulfonyl)ethyl)sulfilimine 
• 66094-96-0 N-[(R)-((R)-4-tert-butoxycarbonyl-5-cyano-3,6-dihydro-2H-[1,3]thiazin-2-yl)-(2-phenoxy-acetylamino)-acetyl]-S,S-diphenyl-sulfimide 
• 42787-33-7 S,S-Diphenyl-N-chlorosulfilimine 
• 42787-34-8 S,S-Diphenyl-N_.bromosulfilimine 
• 42787-35-9 S,S-Diphenyl-N-iodosulfilimine 
• 39149-62-7 S,S-diphenyl-N-(ethoxycarbonyl)sulfilimine 
• 39149-63-8 1-(S,S-diphenylsulfilimino)-2,4-dinitrobenzene 
• 42397-43-3 N-(Phenylcarbamoyl)-diphenylsulfilimin 

Relevant academic research and scientific papers

Novel diphenylsulfimide antioxidants containing 2,6-di-tert-butylphenol moieties

New diphenylsulfimide derivatives containing substituents with the 2,6-di-tert-butylphenol moiety at the nitrogen atom were synthesized. Their molecular structures were established by X-ray diffraction. Antioxidant activity was experimentally evaluated by spectrophotometry based on hydrogen transfer to the stable radicals, namely, 2,2-diphenyl-1-picrylhydrazyl and the 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radical cation (ABTS·+), and using in vitro lipid peroxidation in rat brain and liver homogenates. The presence of phenol and diphenylsulfimide moieties in one molecule leads to a significant enhancement of antioxidant activity. The new compounds exhibit moderate inhibitory activity against enzymes involved in carbohydrate and lipid metabolism. The evaluation of antiglycation activity showed that the new sulfimides taken at a concentration of 100 μmol L–1 have activity comparable with that of aminoguanidine.

Direct Thioamination of Arynes via Reaction with Sulfilimines and Migratory N-Arylation

A novel method for preparing a diverse range of o-sulfanylanilines is described. Direct thioamination of arynes with sulfilimines gives o-sulfanylanilines, involving C-N and C-S bond formations and migratory N-arylation.

Synthesis and chemistry of enantiomerically pure 10,11-dihydrodibenzo[b,f] thiepines

Several chiral thiepines were efficiently constructed using sulfur diimidazole in combination with a variety of bislithiated carbon fragments. The sulfur atom in these thiepines is found to be unusually unreactive compared to diphenylsulfide. The Royal Society of Chemistry 2006.

Rhodium-catalyzed imination of sulfoxides and sulfides: Efficient preparation of N-unsubstituted sulfoximines and sulfilimines

The Rh(II)-catalyzed imination of sulfoxides and sulfides using [Rh 2(OAc)4] as a catalyst and trifluoroacetamide or sulfonylamides in combination with iodobenzene diacetate and magnesium oxide affords sulfoximines and sulfilimines, respectively, in a stereospecific manner.

Synthesis, Structure, and Thermolysis Mechanism of S-Alkoxythiazynes

S-Alkoxy-S,S-diarylthiazynes were prepared by two methods: the alkaline hydrolysis of S,S-diaryl-N-halosulfilimines in aqueous alcohols and the reaction of S,S-diaryl-S-fluorothiazynes with sodium alkoxides. The structure of S,S-diphenyl-S-propoxythiazyne was determined by an X-ray crystallographic analysis, which showed a short SN bond length of 1.441(3) A. The thermolysis of S-alkoxythiazynes gave elimination products, which were identified as the corresponding carbonyl compounds and N-unsubstituted S,S-diarylsulfilimines. Kinetic experiments for the thermolysis of the S-alkoxy-S,S-diarylthiazynes were carried out. The first-order kinetic behavior, a large kinetic isotope effect (kHkD = 6.1 ) using S,S-diphenyl-S-[1,1-2H2]propoxythiazyne, a negative activation entropy (ΔS? = -30 J K-1mol-1), and a negative Hammett ρ-value (ρ= -0.35) on the phenyl group were obtained, suggesting that the reaction proceeds via a concerted five-membered cyclic transition state. A deviation from the ideal concerted transition state is discussed in comparison with that for sulfoxides.

Preparation and Reactivities of S,S-Diaryl-S-aminothiazynes, Ar2S(NR2)(N)

Reaction of S,S-diaryl-S-fluorothiazynes with cyclic secondary amines gave novel thiazynes, the corresponding S-aminothiazynes in good yields.Spectroscopic studies, measurement of pKa values, pyrolysis and alkylation reactions of the aminothiazynes were carried out.

Kinetic Study on the Alkaline Hydrolysis of S,S-Diaryl-N-halosulfilimines

Kinetics for the alkaline hydrolysis of S,S-diaryl-N-bromosulfilimines were carried out in aqueous methanol.The observed pseudo-first-order rate constants were found to give a linear correlation with the concentration of sodium hydroxide, k=k1+k2.The first-order rate constants k1 showed a large negative Hammett ρ value (-2.43) for the substituent effect on the phenyl group, nearly zero activation entropy (-0.9+/-13.1 JK-1mol-1) and a relatively large m value (0.638) against the solvent ionizing power Y value suggesting that the reaction process fork1 close to SN1.The salt effect, the deuterium solvent isotope effect and the steric effect are also in accord with the SN1 mechanism.On the other hand, the second order rate constants k2 revealed a small Hammett ρ value, a negative activation entropy (-44.0+/-4.0 JK-1mol-1), a small m value (0.153) and a steric deceleration by ortho substituents showing that the reaction for k2 is SN2-like.The salt effect and the solvent isotope effect are also compatible with the SN2-like mechanism.Meanwhile, the k1 for S,S-diphenyl-N-halosulfilimines remarkably increased in the order of N-iodo N-bromo N-chloro.This reactivity might be due to the lone pair-lone pair repulsion at the reactant state.From these observations, the alkaline hydrolysis of S,S-diaryl-N-halosulfilimines was confirmed to proceed via concurrent two mechanisms, the SN1-like mechanism involving nitridosulfonium cation as an intermediate and the SN2'-like mechanism with the transition state in which the N-X bond cleavage is more progressed than the S-O bond formation with nucleophiles (-OH, -OMe).