60011-16-7

Basic information

• Product Name: (S)-tert-Butanethiosulfinate
• Synonyms: (S)-S-TERT-BUTYL 2-METHYLPROPANE-2-SULFINOTHIOATE;discontinued (S)-S-tert-Butyl 2-Methylpropane-2-sulfinothioate;(S)-(-)-TERT-BUTYL TERT-BUTANETHIOSULFINATE;(S)-TERT-BUTANETHIOSULFINATE;S-(tert-butyl) (S)-2-methylpropane-2-sulfinothioate;2-Propanesulfinothioic acid, 2-methyl-, S-(1,1-dimethylethyl) ester, [S(S)]-
• CAS NO: 60011-16-7
• Molecular Formula: C₈H₁₈OS₂
• Molecular Weight: 137.24
• Product Categories: API intermediates
• Mol File: 60011-16-7.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 209.3 °C at 760 mmHg
• Flash Point: 80.4 °C
• Appearance: /
• Density: 1.055±0.06 g/cm3(Predicted)
• Refractive Index: 1.542
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: (S)-tert-Butanethiosulfinate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-tert-Butanethiosulfinate(60011-16-7)
• EPA Substance Registry System: (S)-tert-Butanethiosulfinate(60011-16-7)

Safety Data

• Hazardous Substances Data: 60011-16-7(Hazardous Substances Data)

Usage

General Description

(S)-tert-Butanethiosulfinate is a chemical compound that belongs to the class of organic sulfur compounds known as thiosulfinate. It is commonly referred to as TBSI. (S)-tert-Butanethiosulfinate is a chiral molecule, meaning it exists in both left and right-handed forms. (S)-tert-Butanethiosulfinate has been found to exhibit antimicrobial, antifungal, and insecticidal properties. It is commonly used as a flavoring agent and food preservative due to its ability to inhibit the growth of microorganisms. Additionally, (S)-tert-Butanethiosulfinate has shown potential in medical applications, such as in the treatment of bacterial infections and as an antioxidant. Overall, (S)-tert-Butanethiosulfinate is a versatile chemical with various applications in different industries.

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

• 4850-72-0 (S)-(-)-(tert-butylsulfinyl)benzene 
• 1092722-63-8 1-(S)-(-)-tert-butylsulfinyl-3-methoxybenzene 
• 1092722-65-0 1-(S)-(-)-tert-butylsulfinyl-3-(methoxymethoxy)benzene 
• 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 
• 1310800-19-1 C₂₁H₂₆O₄S 

Relevant articles and documents

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.

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.

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

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.