4972-29-6

Usage

Synthesis Reference(s)

Tetrahedron Letters, 33, p. 3973, 1992 DOI: 10.1016/0040-4039(92)88076-H

Safety Profile

May explode if stored in a sealedcontainer. When heated to decomposition it emits toxicfumes of SOx and Cl-.

Upstream product

• 5539-54-8 N,N-dimethylbenzenesulfinamide 
• 4972-30-9 benzenesulfinic benzenesulfonic anhydride 
• 32637-30-2 N-(phenylthiomethyl)phthalimide 
• 934-87-2 S-phenyl thioacetate 
• 85533-19-3 1-benzenesulfinyl-2-trimethylsilylethane 
• 98-09-9 benzenesulfonyl chloride 
• 108-98-5 thiophenol 
• 17988-59-9 phenyl 2-(trimethylsilyl)ethyl sulfide 
• 71-43-2 benzene 
• 7719-09-7 thionyl chloride 
• 618-41-7 Benzenesulfinic acid 
• 873-55-2 sodium benzenesulfonate 
• 882-33-7 diphenyldisulfane 
• 3989-48-8 1-(methanesulfonyl)piperidine 

Downstream Products

• 7205-94-9 chloromethyl phenyl sulfoxide 
• 4972-31-0 1-benzenesulfinyl piperidine 
• 670-98-4 methyl benzenesulfinate 
• 19726-93-3 N-benzenesulfenyl-N'-phenyl-urea 
• 1208-20-4 S-phenyl benzenethiosulfinate 
• 26974-27-6 S-p-tolyl benzenethiosulfinate 
• 1212-08-4 S-Phenyl benzenethiosulfonate 
• 599-94-0 1,2-bis(phenylsulfonyl)ethane 
• 882-33-7 diphenyldisulfane 
• 91137-89-2 2-acetamido-5-phenylthiothiazole 
• 5469-22-7 N-(p-methylphenyl)benzenesulfinamide 
• 14934-02-2 N-(4-Chlorophenyl)benzenesulfinamide 
• 14934-04-4 N-(4-methoxyphenyl)benzenesulfinamide 
• 63752-74-9 S-tert-butyl benzenesulfinothioate 

Relevant academic research and scientific papers

A FACILE SYNTHESIS OF SULFINYL CHLORIDES FROM THIOLACETATES

Alkyl and aryl thiolacetates are converted smoothly into sulfinyl chlorides by sulfuryl chloride in the presence of acetic anhydride.

Regio- and Stereoselective Chloro Sulfoximidations of Terminal Aryl Alkynes Enabled by Copper Catalysis and Visible Light

By visible-light photoredox catalysis with copper complexes, sulfoximidoyl chlorides add to terminal aryl alkynes to give the corresponding (E)-β-chlorovinyl sulfoximines with exclusive regio- and stereoselectivities in high yields. Two representative pro

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

General Method for the Asymmetric Synthesis of N-H Sulfoximines via C-S Bond Formation

A versatile method for the synthesis of enantioenriched N-H sulfoximines is reported. The approach stems from the organomagnesium-mediated ring opening of novel cyclic sulfonimidate templates. The reactions proceed in high yield and with excellent stereofidelity with alkyl, aryl, and heteroaryl Grignard reagents. The chiral auxiliary is readily removed from the resultant sulfoximines via an unusual oxidative debenzylation protocol that utilizes molecular oxygen as the terminal oxidant. This provides a general strategy for the synthesis of highly enantioenriched N-H sulfoximines.

Rapid Deoxyfluorination of Alcohols with N-Tosyl-4-chlorobenzenesulfonimidoyl Fluoride (SulfoxFluor) at Room Temperature

The deoxyfluorination of alcohols is a fundamentally important approach to access alkyl fluorides, and thus the development of shelf-stable, easy-to-handle, fluorine-economical, and highly selective deoxyfluorination reagents is highly desired. This work describes the development of a crystalline compound, N-tosyl-4-chlorobenzenesulfonimidoyl fluoride (SulfoxFluor), as a novel deoxyfluorination reagent that possesses all of the aforementioned merits, which is rare in the arena of deoxyfluorination. Endowed by the multi-dimensional modulating ability of the sulfonimidoyl group, SulfoxFluor is superior to 2-pyridinesulfonyl fluoride (PyFluor) in fluorination rate, and is also superior to perfluorobutanesulfonyl fluoride (PBSF) in fluorine-economy. Its reaction with alcohols not only tolerates a wide range of functionalities including the more sterically hindered alcoholic hydroxyl groups, but also exhibits high fluorination/elimination selectivity. Because SulfoxFluor can be easily prepared from inexpensive materials and can be safely handled without special techniques, it promises to serve as a practical deoxyfluorination reagent for the synthesis of various alkyl fluorides.

N-Trifluoromethylthiolated Sulfonimidamides and Sulfoximines: Anti-microbial, Anti-mycobacterial, and Cytotoxic Activity

Herein we demonstrate the expanded utility of a recently described N-trifluoromethylthiolation protocol to sulfonimidamide containing substances. The novel N-trifluoromethylthio sulfonimidamide derivatives thus obtained were evaluated for antibacterial activity against Mycobacterium tuberculosis (M. tb.) and Mycobacterium abscessus and Gram + Ve (Streptococcus aureus, Bacillus subtilis), and Gram - Ve (Escherichia coli, Pseudomonas aeruginosa) bacteria. Two compounds, 13 and 15 showed high antimycobacterial activity with MIC value of 4-8 μg/mL; i.e. comparable to WHO recommended first line antibiotic for TB infection ethambutol. The same compounds were also found to be cytotoxic in HepG2 cells (compound 13 IC50 = 15 μg/mL; compound 15 IC50 = 65 μg/mL). A structure activity relationship, using matched pair analysis, gave the unexpected conclusion that the trifluoromethylthio moiety was responsible for the cellular and bacterial toxicity. Given the increasing use of the trifluoromethylthio group in contemporary medicinal chemistry, this observation calls for considerations before implementation of the functionality in drug design.

Sulfinate-Organocatalyzed (3+2) Annulation Reaction of Propargyl or Allenyl Sulfones with Activated Imines

An operationally simple methodology for the synthesis of 4-sulfonyl-3-pyrrolines is described using a propargylic sulfone and N-sulfonyl imines as substrates. This annulation process is initiated by an arenesulfinate organocatalyst, which allows a smooth isomerization of the alkynyl precursor into the corresponding allene, followed by the generation of a highly reactive allyl sulfone anion. An asymmetric version involving an unprecedented enantiopure sulfinate–ammonium cooperative ion pair (PhSO2– R4N+*) was investigated. A proof-of-concept, with enantiomeric excesses of up to 41 %, was obtained according to a preliminary screening of commercially available chiral phase-transfer catalysts.

Sulfinate-Organocatalyzed (3+2) Annulation of Allenyl Sulfones with 1,1-Dicyano Olefins in the Presence of a Quaternary Ammonium Phase Transfer Agent

The benzenesulfinate-catalyzed (3+2) annulation between allenyl sulfones and aryl(alkyl)idenemalononitriles has been developed under mild phase transfer conditions, affording a breadth of functionalized sulfonyl cyclopentenes in good to excellent yields (

Sulfonimidates: Useful Synthetic Intermediates for Sulfoximine Synthesis via C-S Bond Formation

Medicinally relevant sulfoximines are accessed from C-S coupling of sulfonimidates and commercially available organomagnesium reagents. Sulfonimidates are conveniently synthesized by oxidative alkoxylation of readily available sulfinamides. This constitutes a general C-S coupling approach for the synthesis of sulfoximines.

One-pot synthesis of α-phenylsulfinyl ketones by reaction of phenyl benzenethiosulfinate with enolate anions, and synthesis of sulfoxides and sulfides by its reaction with Grignard reagents

Phenyl benzenethiosulfinate reacts with enolate anions derived from ketones to give α-phenylsulfinyl ketones directly, together with minor amounts of α-phenylsulfanyl ketones. These are easily separated by forming the water-soluble sodium salts of the sulfinyl compounds. Grignard reagents also react with phenyl benzenethiosulfinate, to give mixtures of sulfoxides and sulfides.