60011-16-7

Usage

Uses

Used in Food Industry:
(S)-tert-Butanethiosulfinate is used as a flavoring agent and food preservative for its ability to inhibit the growth of microorganisms, thereby extending the shelf life and maintaining the quality of food products.
Used in Medical Applications:
(S)-tert-Butanethiosulfinate is used as an antimicrobial agent for the treatment of bacterial infections, leveraging its ability to target and eliminate harmful microorganisms.
Used in Antioxidant Applications:
(S)-tert-Butanethiosulfinate is used as an antioxidant, protecting cells and tissues from oxidative damage and promoting overall health and well-being.

InChI:InChI=1/C4H10OS2/c1-4(2)3-7(5)6/h4H,3H2,1-2H3,(H,5,6)/p-1

Upstream product

• 110-06-5 di-tert-butyl disulfide 

Downstream Products

• 1067199-21-6 tert-butyl 3-(3-(2-(tertbutylsulfinyl)phenyl)-1,3-dimethylureido)phenylmethylcarbamate 
• 1114451-36-3 1-(2-(1,3-dioxolan-2-yl)phenyl)-1,3-dimethyl-3-(3-(3-phenyl-1,3-dimethyl-ureido)phenyl)urea 
• 1114451-35-2 1-(2-(1,3-dioxolan-2-yl)phenyl)-1,3-dimethyl-3-(3-(3-(2-(tert-butylsulfinyl)phenyl)-1,3-dimethyl-ureido)phenyl)urea 
• 1114451-18-1 1-(2-(1,3-dioxolan-2-yl)phenyl)-3-(2-(tert-butylsulfinyl)phenyl)-1,3-dimethylurea 
• 343338-28-3 (S)-2-methylpropane-2-sulfinamide 
• 1310800-06-6 C₁₉H₂₂O₂S 
• 1310800-07-7 C₁₉H₂₂O₂S 
• 1310800-05-5 C₁₈H₂₀OS 
• 1310799-90-6 C₁₂H₁₆OS 
• 1310800-15-7 C₂₂H₂₂OS 
• 1310800-16-8 C₂₄H₂₄OS 
• 1310800-22-6 C₂₃H₃₀O₆S 
• 1310800-21-5 C₂₁H₂₆O₄S 
• 1310800-20-4 C₂₀H₂₄O₃S 

Relevant academic research and scientific papers

Facile optical resolution of tert-butanethiosulfinate by molecular complexation with (R)-BINOL and study of chiral discrimination of the diastereomeric complexes

An important synthon, tert-butanethiosulfinate (2), has been effectively resolved by forming molecular complexes with (R)-2,2′-dihydroxy-1,1′-binaphthyl (BINOL, 3) in high enantioselectivity (> 99% ee). The present procedure represents the first example of the resolution of thiosulfinate. The mechanism of chiral discrimination is discussed in terms of molecular recognition based on IR and X-ray analyses of the diastereomeric complexes during the resolution. In the less-soluble complex, (R)-3 and (R)-2 self-assembled as a linear supramolecule; however, in the more-soluble complex, (R)-3 and (S)-2 formed a simple bimolecular complex by one stronger hydrogen bond. Hydrogen bonding is the major driving force for effective resolution.

An Economic Approach to Chiral Thiosulfinates by Enantioselective Oxidation with Hydroperoxide

Some novel chiral ligands and VO(acac)2 were utilized to catalytic asymmetric oxidation of disulfides. The optically active thiosulfinates were obtained.

Enantioselective oxidation of di-tert-butyl disulfide with a vanadium catalyst: Progress toward mechanism elucidation

The mechanism of the oxidation of di-tert-butyl disulfide (1) to the chiral thiosulfinate (2) by H2O2 catalyzed by bis(acetylacetonato)oxovanadium and a chiral Schiff-base ligand (3) has been investigated. Techniques included 51V NMR spectroscopy, solvent effects on reaction enantioselectivity, and the isolation and full characterization of a 2:1 ligand-to-vanadium catalyst precursor. A model for the dramatic solvent effect on the enantioselectivity of this reaction was developed, based on the identification of a competing nonselective oxidation pathway. From this model, strategies for limiting this competing pathway were developed.

Process for synthesizing chiral tert-butanesulfinyl amide

The invention discloses a process for synthesizing chiral tert-butanesulfinyl amide. The process includes carrying out reaction on tert-butyl mercaptan and iodine/hydrogen peroxide acetone to generate di-tert-butyl disulfide; oxidizing hydrogen peroxide under the catalytic effect of vanadium to generate chiral tert-butyl sulfenyl tert-butyl mercaptide; carrying out one-pot reaction on the chiral tert-butyl sulfenyl tert-butyl mercaptide and lithium reagents/liquid ammonia in the presence of alkyl chloride to obtain the tert-butanesulfinyl amide. Compared with existing processes, the process has the advantages that the smoothness of the process can be enhanced, the usage of the liquid ammonia can be reduced to a great extent, and the operational efficiency can be improved.

Enantioselective organocatalytic oxidation of functionalized sterically hindered disulfides

Figure presented The first study on enantioselective oxidation of functionalized sterically hindered disulfides is reported. This study shows that the Shi organocatalytic system using carbohydrate-derived ketone with oxone is superior to the Ellman-Bolm v

Catalytic enantioselective oxidation of sulfides and disulfides by a chiral complex of bis-hydroxamic acid and molybdenum

A chiral bis-hydroxamic acid (BHA)-molybdenum complex was used for the catalytic asymmetric oxidation of sulfides and disulfides utilizing one equivalent of alkyl peroxide with yields up to 83% and ee up to 86%. An extension of our methodology combines the asymmetric oxidation with kinetic resolution providing excellent enantioselectivity (ee 92-99%).

Contra-Friedel-Crafts tert-butylation of substituted aromatic rings via directed metallation and sulfinylation

Directed metallation and sulfinylation yields sulfoxides which undergo ipso nucleophilic aromatic substitution with tertiary and secondary alkyllithiums, giving aromatic rings bearing alkyl groups generally incompatible with directed metallation methods and with regioselectivity complementary with classical Friedel-Crafts substitution. The Royal Society of Chemistry 2006.

Enantioselective synthesis of thiosulfinates and of acyclic alkylidenemethylene sulfide sulfoxides

Enantioselectivities up to 75 % have been found in the catalytic mono-oxidation of di-tert-butyl disulfide and related compounds as well as of ketene-S,S-acetals with an in situ generated chiral dioxirane. The effect of solvents on the enantiomeric excess

Improved synthesis of tert-butanesulfinamide suitable for large-scale production

(Matrix presented) An improved synthesis of tert-butanesulfinamide that overcomes the scalability problems of the previous syntheses is described. The key step is the catalytic asymmetric oxidation of the inexpensive di-tert-butyl disulfide starting material. The new homogeneous reaction conditions utilize an inexpensive chiral ligand prepared in a single step from commercially available cis-1-amino-indan-2-ol. The reaction is performed at a 2.3 M concentration in the practical solvent acetone and can readily be run on a kilogram scale.