3541-14-8

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
S-Phenyl 4-methylbenzenesulfonothioate is used as an intermediate in the synthesis of various pharmaceuticals and agrochemicals. Its unique structure allows it to be a valuable component in the development of new drugs and agricultural products.
Used as a Reagent in Organic Synthesis:
S-Phenyl 4-methylbenzenesulfonothioate is commonly used as a reagent in organic synthesis for the preparation of sulfur-containing compounds. Its ability to form stable bonds with sulfur makes it a useful building block for creating complex organic molecules.
Safety Precautions:
It is important to handle S-Phenyl 4-methylbenzenesulfonothioate with care as it may be harmful if ingested, inhaled, or comes into contact with the skin. Proper safety measures should be taken to minimize exposure and ensure the safe use of S-phenyl 4-methylbenzenesulfonothioate in research and industrial applications.

Upstream product

• 536-57-2 p-toluene sulfinic acid 
• 931-59-9 benzenesulfenyl chloride 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 1208-20-4 S-phenyl benzenethiosulfinate 
• 71032-18-3 C₁₃H₁₂O₂S₃ 
• 35662-09-0 2-phenylsulfanyl-2,3-dihydro-1H-indane-1,3-dione 
• 882-33-7 diphenyldisulfane 
• 98-11-3 benzenesulfonic acid 
• 14204-24-1 N-(phenylthio)succinimide 
• 1192-40-1 copper(I) thiophenolate 
• 108-98-5 thiophenol 
• 2637-34-5 2-Sulfanylpyridine 
• 103-19-5 di(p-tolyl) disulfide 
• 29627-34-7 4-(phenyldisulfanyl)toluene 

Downstream Products

• 139-66-2 diphenyl sulfide 
• 2943-42-2 di(4-methyl)phenylthiosulfonate 
• 33667-80-0 phenyl mesityl sulfide 
• 3128-42-5 S-phenyl 4-methylbenzothioate 
• 60623-60-1 2-(phenylthio)tetrahydrofuran 
• 5718-98-9 benzoyl-phenyl-disulfane 
• 29627-34-7 4-(phenyldisulfanyl)toluene 
• 109100-37-0 anilinium p-toluenesulfinate 
• 103-19-5 di(p-tolyl) disulfide 
• 882-33-7 diphenyldisulfane 
• 899-02-5 (2,4-dinitro-phenyl)-p-tolyl sulfone 

Relevant academic research and scientific papers

Formal Total Synthesis of (+)-C9-Deoxyomuralide from l -Leucine Using a Double Sacrificial Chirality Transfer Approach

Formal stereocontrolled syntheses of (±)- and (+)-C9-deoxyomuralide is reported, constituting one of the shortest routes to the full carbon skeleton reported to date.

Visible-Light-Induced Radical Cascade Reaction of 1-Allyl-2-ethynylbenzoimidazoles with Thiosulfonates to Assemble Thiosulfonylated Pyrrolo[1,2-a]benzimidazoles

A visible-light-induced radical domino reaction of 1-allyl-2-ethynylbenzoimidazoles with thiosulfonates was developed, which generated the thiosulfonylated pyrrolo[1,2-a]benzimidazoles in moderate to good yields. This reaction proceeded under transition-metal-free conditions with good functional group tolerance and high regioselectivity. The possible pathway involved thiosulfonates were activated through the energy transfer route promoted by photocatalysis.

Nickel-Catalyzed Difunctionalization of Alkynyl Bromides with Thiosulfonates and N -Arylthio Succinimides: A Convenient Synthesis of 1,2-Thiosulfonylethenes and 1,1-Dithioethenes

An efficient nickel-catalyzed vicinal thiosulfonylation of 1-bromoalkynes with thiosulfonates in the presence of cesium carbonate is described. An operationally simple and highly regioselective atom transfer radical addition (ATRA) of alkynyl bromides provides a wide range of (E)-1,2-thiosulfonylethenes (α-aryl-β-thioarylvinyl sulfones) in moderate to high yields. The extensive substrate scope of both alkynyl bromides and thiosulfonates is explored with a broad range of functional groups. Indole-derived 1,1-bromoalkenes were also successfully explored in this 1,2-thiosulfonylation process. Moreover, the nickel-catalyzed geminal -dithiolation of alkynyl bromides with N -arylthio succinimides provides 1,1-dithioalkenes in high yields. The present protocol is reliable on gram scale, and a sequential one-pot bromination and thiosulfonylation of phenylacetylene is achieved in a scale-up synthesis. Following control experiments, a plausible mechanism is proposed to rationalize the experimental outcome and the vicinal thio-sulfonylation.

Atom transfer radical addition to styrenes with thiosulfonates enabled by synergetic copper/photoredox catalysis

A synergetic copper/photoredox catalyzed ATRA of styrenes and thiosulfonates is developed. Besides aryl ethylenes, the challenging α-substituted styrenes were employed to construct the benzylic quaternary carbon centers. Owing to the mild conditions as well as the high level of substrate compability, this ATRA could be applied to derivatize bioactive natural products in late stage, and to install fluorophores across alkenes. The mechanistic studies reveal sulfonyl radicals as the key intermediate in the transformation.

Visible-light-promoted synthesis of secondary and tertiary thiocarbamates from thiosulfonates andN-substituted formamides

A general visible-light-promoted metal-free synthesis of secondary and tertiary thiocarbamates starting from thiosulfonates andN-substituted formamides is developed. By employing rhodamine B as a photocatalyst andtert-butyl hydroperoxide (TBHP) as an oxidant, a wide scope of thiocarbamates can be obtained through direct thiolation of acyl C-H bonds under irradiation of blue light at room temperature for 12 h.

An iodine-mediated new avenue to sulfonylation employingN-hydroxy aryl sulfonamide as a sulfonylating agent

A novel and highly efficient I2/K2CO3mediated regioselective sulfonylation of thiophenols, aryl acetylenic acid and aromatic alkynes withN-hydroxy sulfonamide has been developed.N-hydroxy sulfonamide has been used for the first time for the synthesis of these sulfones. The scope and versatility of the reaction has been demonstrated by the regio- and stereoselective synthesis of different analogs of sulfones with various structural features.

Organophotoredox-Catalyzed Formation of Alkyl-Aryl and -Alkyl C-S/Se Bonds from Coupling of Redox-Active Esters with Thio/Selenosulfonates

A mild organophotoredox synthetic protocol for forming a Csp3-S/Se bond by reacting widespread redox-active esters with thio/selenosulfonates has been developed. The power of the synthetic manifold is fueled by an unprecedented broad substrate scope and wide functional group tolerance.

CuCl2-promoted decomposition of sulfonyl hydrazides for the synthesis of thiosulfonates

Sulfonyl hydrazides recently received much attention as reagents for the introduction of sulfur-containing functional groups into organic compounds, because both sulfonyl and sulfenyl sources could be generated by the oxidation and decomposition of the sulfonyl hydrazides, respectively. However, the transformations of sulfonyl hydrazides into thiosulfonates, which could be produced by the reaction between sulfonyl and sulfenyl sources, have been less investigated. In this manuscript, we describe CuCl2-promoted selective synthesis of thiosulfonates from sulfonyl hydrazides. A variety of thiosulfonates were produced in moderate to good yields. The mechanism involving radical intermediates such as sulfonyl radical and thiyl radical was proposed on the basis of the previously reported references and mechanistic investigations. In addition, quantum chemical simulations revealed that Cu-promoted decomposition of sulfonyl hydrazides is thermodynamically viable in the developed conditions.

Metal-Free Chemoselective Reaction of Sulfoxonium Ylides and Thiosulfonates: Diverse Synthesis of 1,4-Diketones, Aryl Sulfursulfoxonium Ylides, and β-Keto Thiosulfones Derivatives

A diverse chemoselective insertion reaction of sulfoxonium ylides and thiosulfonates under transition-metal-free conditions is developed, which successfully affords 1,4-diketone compounds, arylthiosulfoxide-ylides, and β-keto thiosulfones, respectively. The nucleophilic addition of two molecular sulfoxonium ylides to construct sulfone-substituted 1,4-dione compounds is the highlight of this work.

Ammonium iodide-mediated electrosynthesis of unsymmetrical thiosulfonates from arenesulfonohydrazides and thiols

Unsymmetrical thiosulfonates were synthesized from thiols and arenesulfonohydrazides by their electrolysis in undivided cell equipped with graphite anode and stainless steel cathode under high current density applying NH4I both as a redox catal