1197-26-8

Usage

Uses

Used in Pharmaceutical Research:
PHENYLMETHANETHIOSULFONATE is used as a probe for [investigating the structures of important biological channels and transporters] because of its ability to react specifically and rapidly with thiols to form mixed disulfides.
Used in the Study of ACh Receptor Channel:
PHENYLMETHANETHIOSULFONATE is used as a structural probe for [the ACh receptor channel] to help researchers understand the mechanisms and structures of this crucial receptor channel in the nervous system.
Used in the Study of GABA Receptor Channel:
PHENYLMETHANETHIOSULFONATE is used as a structural probe for [the GABA receptor channel] to aid in the investigation of the structure and function of this essential receptor channel in the central nervous system.
Used in the Study of Lactose Permease:
PHENYLMETHANETHIOSULFONATE is used as a structural probe for [lactose permease] to gain insights into the transport mechanisms and structural aspects of this important membrane protein involved in lactose transport.

InChI:InChI=1/C7H8O2S2/c1-11(8,9)10-7-5-3-2-4-6-7/h2-6H,1H3

Upstream product

• 14173-25-2 methyl phenyl disulfide 
• 67-68-5 dimethyl sulfoxide 
• 108-98-5 thiophenol 
• 124-63-0 methanesulfonyl chloride 
• 98-09-9 benzenesulfonyl chloride 
• 4972-29-6 benzenesulphinyl chloride 
• 873-55-2 sodium benzenesulfonate 
• 6829-66-9 N-butylbenzenesulfinamide 
• 20277-69-4 sodium methansulfinate 
• 882-33-7 diphenyldisulfane 
• 14204-24-1 N-(phenylthio)succinimide 
• 931-59-9 benzenesulfenyl chloride 
• 624-92-0 Dimethyldisulphide 
• 40249-95-4 S-phenyl methanethiosulfinate 

Downstream Products

• 1374694-90-2 6-endo-methylsulfonyl-7-syn-phenylsulfanylbicyclo[3.1.1]heptane 
• 1374694-93-5 6-endo-methylsulfonyl-7-anti-phenylsulfanylbicyclo[3.1.1]heptane 

Relevant academic research and scientific papers

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.

Direct conversion of sulfinamides to thiosulfonates without the use of additional redox agents under metal-free conditions

Direct conversion of sulfinamides to thiosulfonates is described. Without the use of additional redox agents, the reaction proceeds smoothly in the presence of TFA under metal-free conditions. This protocol possesses many advantages such as odourless and stable starting materials, broad substrate scope, selective synthesis, and mild reaction conditions. This journal is

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.

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.

Disproportionate Coupling Reaction of Sodium Sulfinates Mediated by BF3·OEt2: An Approach to Symmetrical/Unsymmetrical Thiosulfonates

The BF3·OEt2-mediated disproportionate coupling reaction of sodium sulfinates was found for the first time. In this reaction, various S-S(O)2 bonds can be formed, efficiently giving thiosulfonates in moderate to excellent yields. As a convenient protocol for the synthesis of symmetrical and unsymmetrical thiosulfonates, its reaction mechanism involves the formation of a thiyl radical and sulfonyl radical via a sulfinyl radical disproportionation. What is more, this transformation can also be applied practically as a gram-scale reaction and to the two-step synthesis of sulfone and sulfonamide in one pot in situ using thiosulfonate as an intermediate.

Tunable and Practical Synthesis of Thiosulfonates and Disulfides from Sulfonyl Chlorides in the Presence of Tetrabutylammonium Iodide

A tunable and practical synthesis of electrophilic sulfenylating reagents, thiosulfonates and disulfides, from inexpensive and easily available sulfonyl chlorides, has been developed. By appropriate choice of solvents, the reaction of sulfonyl chlorides and tetrabutylammonium iodide gave the target products in good to excellent yields, respectively. These transformations probably proceed through a reducing–coupling pathway. (Figure presented.).

Iodide-Catalyzed Synthesis of Secondary Thiocarbamates from Isocyanides and Thiosulfonates

A new method for the synthesis of secondary thiocarbamates from readily available isocyanides and thiosulfonates with broad functional group tolerance is reported. The reaction proceeds under mild reaction conditions in isopropanol and is catalyzed by inexpensive sodium iodide.

Sc(OTf)3-catalyzed synthesis of thiosulfonates in ionic liquid-water

The first example of Sc(OTf)3-catalyzed sulfenylation of sodium sulfinates with N-(organothio)succinimides in ionic liquids (ILs) and water cosolvent system was developed, achieving thiosulfonates in moderate to excellent yields. Additionally, Sc(OTf)3/ILs could be recovered easily after the reactions and reused without a significant loss in the catalytic activity. Thus, the present protocol represents an interesting complement to known methods for thiosulfonates synthesis.

A new synthesis of cytotoxic thiosulfonates and the first synthesis of deuterated thiosulfonates

A new synthesis of thiosulfonates starting from thiophenols and cyanuric chloride activated dimethyl sulfoxide is reported herein. Although the yields of the reactions are moderate, this method enables the incorporation of the SCD3 group of dimethyl sulfoxide-d6 into thiosulfonates. This is the first synthesis of deuterated thiosulfonates with a labeling purity above 99%. In addition, the cytotoxicity of the thiosulfonates is reported for the first time. Georg Thieme Verlag Stuttgart. New York.

Antifungal thiosulfonates: Potency with some selectivity

A series of thiosulfonates have been prepared and tested against Aspergillus niger and Aspergillus flavus. In general, the thiosulfonates are moderate antifungal agents - more potent than corresponding inactive disulfides and less potent than corresponding very active fungitoxic disulfides. A pair of thiosulfonates show high selectivity, each killing only one kind of fungus. CSIRO 2000.