13882-12-7

Basic information

• Product Name: methyl methanethiosulfinate
• Synonyms: methyl methanethiosulfinate;METHYLMETHANETHIOSULPHINATE;DIMETHYLTHIOSULPHINATE;Methane methyl thiosulphinate;Methanesulfinothioic acid S-methyl ester;Methanethiosulfinic acid S-methyl ester;Methyl(methylsulfinyl) sulfide;S-Methyl methanesulfinothioate
• CAS NO: 13882-12-7
• Molecular Formula: C₂H₆OS₂
• Molecular Weight: 110.20
• Mol File: 13882-12-7.mol

Chemical Properties

• Boiling Point: 121.2°C
• Flash Point: 76.5°C
• Appearance: /
• Density: 1.160 (estimate)
• Vapor Pressure: 0.407mmHg at 25°C
• Refractive Index: 1.5700 (estimate)
• CAS DataBase Reference: methyl methanethiosulfinate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl methanethiosulfinate(13882-12-7)
• EPA Substance Registry System: methyl methanethiosulfinate(13882-12-7)

Safety Data

• Hazardous Substances Data: 13882-12-7(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 12, p. 299, 1971 DOI: 10.1016/S0040-4039(01)96424-X

InChI:InChI=1/C2H6OS2/c1-4-5(2)3/h1-2H3

Upstream product

• 79-21-0 peracetic acid 
• 624-92-0 Dimethyldisulphide 
• 67-66-3 chloroform 
• 93-59-4 Perbenzoic acid 
• 676-85-7 methylsulphinyl chloride 
• 14094-11-2 tert-butyl methyl sulfoxide 
• 10265-92-6 Mio 
• 2229-07-4 methyl radical 
• 74-86-2 acetylene 
• 66625-01-2 bis(methylthio)(methylsulfinyl)methane 
• 4478-93-7 D,L-sulforaphane 
• 74-93-1 methylthiol 
• 3226-62-8 S-methylcysteine sulfoxide 
• 139118-45-9 3-methylsulphinylhexa-1,5-diene 

Downstream Products

• 112688-35-4 N-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-N-(4-benzoyloxy-1-methyl-2-methyldisulfanyl-but-1-en-t-yl)-formamide 
• 2949-92-0 methanethiosulfonic acid S-methyl ester 
• 624-92-0 Dimethyldisulphide 
• 15096-10-3 methyl 2,2-diphenylethenyl sulfide 
• 14173-25-2 methyl phenyl disulfide 
• 17696-73-0 methylsulfinic acid 
• 85084-99-7 methanesulfinic anhydride 
• 85084-98-6 methyl disulfoxide 
• 3658-80-8 dimethyltrisulfane 
• 42474-27-1 2,3,5-trithiahexane 5-oxide 
• 73975-52-7 acetylthiomethyl methyl sulphoxide 
• 1879-16-9 1-methoxy-4-methylsulfanyl-benzene 
• 73682-83-4 methyl 1,2-diphenyl-2-trifluoroacetoxyethyl sulfide 
• 2764-92-3 methyl 1,2-diphenyl-2-hydroxyethyl sulfide 

Relevant articles and documents

SCAVENGING OF RADICALS FROM THE GAS PHASE BY FREEZING WITH DIMETHYL DISULFIDE: 1. TEST OF THE METHOD FOR LIGHT RADICALS.

H and O atoms and methyl radicals produced in microwave discharges of H//2/He, O//2/He and CH//4/He mixtures, respectively, were scavenged by supersonic nozzle probing with subsequent freezing and reaction with dimethyl disulfide on a liquid nitrogen cooled wall. The main reaction products for the three kinds of radicals were CH//3SH, CH//3S(O)SCH//3 and CH//3SCH//3, respectively. The scavenging efficiencies for the different radicals were determined and measured as a function of the gas phase radical concentration, the flow of scavenger molecules, the pressure in the vacuum chamber, and the conditions of the discharge and the flow through the sampling nozzle. It is concluded that this method is suitable for light radicals with reservations in the case of H atoms and can probably be used with still better success for heavier radicals.

Inhibitory effect of methyl methanethiosulfinate on β-glucuronidase activity

Minced or cut-up leaves of Chinese chive (Allium tuberosum Rottler) contain thiosulfinates and their disproportionate reaction products. Among these organosulfur compounds, methyl methanethiosulfinate was found to be an uncompetitive inhibitor of β-glucur

(E,Z)-Ajoene: A potent antithrombotic agent from garlic

A report is presented of the structural characterization and simple synthesis of (E,Z)-ajoene.

Synthesis of a Cyclic 3-Methylsulfonyl Enol Ether

Electrophilic introduction of a methylmercapto group into dihydropyran gives 3-methylmercaptodihydropyran, which is readily oxidized to 3-methylsulfonyldihydropyran.

Photooxidations of Sulfenic Acid Derivatives 2. A Remarkable Solvent Effect on the Reactions of Singlet Oxygen with Disulfides.

Photooxidations of a series of 9 disulfides reveal that the thiosulfinate/thiosulfonate product ratios can be dramatically influenced by the nature of the solvent.The unique ability of methanol to influence this ratio is attributed to nucleophilic addition to a thiopersulfoxide intermediate.

Thermal degradation of sulforaphane in aqueous solution

Sulforaphane, a cancer chemopreventive agent identified from broccoli, was degraded in an aqueous solution at 50 and 100 °C. The reaction mixtures were extracted with methylene chloride and analyzed by gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS). Dimethyl disulfide, S- methyl methylthiosulfinate, S-methyl methylthiosulfonate, methyl (methylthio)methyl disulfide, 1,2,4-trithiolane, 4-isothiocyanato-1- (methylthio)-1-butene, and 3-butenyl isothiocyanate were identified as volatile decomposition products. After methylene chloride extraction, the aqueous layer was dried and silica gel column chromatography was used to separate and purify the nonvolatile decomposition products. The major thermal degradation compound was determined by 1H NMR, 13C NMR, and FAB-MS as N,N'-di(4-methylsulfinyl)butyl thiourea. A possible mechanism for the formation of these products is proposed.

Direct Bis-Alkyl Thiolation for Indoles with Sulfinothioates under Pummerer-Type Conditions

A base-free bis-alkyl thiolation reaction of indoles with sulfinothioates under Pummerer-type conditions is described. Sulfinothioates, activated with 2,2,2-trifluoroacetic anhydride, are demonstrated to be an efficient thiolation reagent for wide applica

A tissue homogenate method to prepare gram-scale allium thiosulfinates and their disulfide conjugates with cysteine and glutathione

The health benefits of Allium vegetables are widely attributed to the enzyme-derived organosulfur compounds called thiosulfinates (TS). However, the lack of a suitable method to prepare TS in good yields has hampered the evaluation of their biological activities. This paper describe a simple enzymatic method using Allium tissue homogenates as a reaction system to prepare gram-scale TS, including those enriched in 1-propenyl groups, which are particularly difficult to obtain. This method is simple, easy to scale up, and requires no column purification step, making it suitable for practical large-scale production of Allium TS. The prepared TS were further utilized to prepare the disulfide conjugates with cysteine and glutathione (CySSR and GSSR, R = methyl, ethyl, propyl, 1-propenyl, and allyl), which are the presumptive metabolites of TS. Among all of the Allium CySSR and GSSR conjugates, the newly prepared glutathione conjugate with 1-propenyl TS, GSSPe, showed the most potent effect to induce quinone reductase (QR, a representative phase II enzyme) in murine hepatoma cells (Hepa 1c1c7) and inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated macrophage cells (RAW 264.7).

Thiophilic addition of organolithiums to trithiocarbonate oxides (sulfines). Synthesis of β-oxoketene dithioacetals, 1,4-dicarbonyl compounds, and allyl sulfoxides

Reaction of trithiocarbonates with meta-chloroperoxybenzoic acid in CH2Cl2 at 0°C affords the corresponding S-oxides. These sulfines are relatively stable comppounds which can be purified by chromatography. They react readily with organolithiums in THF at -78°C in a thiophilic manner to give carbanions which are stabilized by three sulfur groups. Hydrolysis affords trithioorthoester oxides. The thermal behaviour of these hindered products has been investigated and new rearrangenrent processes have been evidenced. The former carbanions are soft nucleophiles: 1,4-addition of these intermediates to α-enones was achieved selectively to lead to β-oxo ketenedithioacetals, which are easily transformed into 4-oxoalkanethioates. This 'Umpolung' route allows the formal use of the (alkylthio)carbonyl anion. A thiophilic addition was also observed with allylsilanes in the presence of n-Bu4NF furnishing allyl sulfoxides.

Unsensitized photooxidation of sulfur compounds with molecular oxygen in solution

The short wavelength irradiation of aliphatic disulfides, sulfides and of n-butanethiol in alcohols or aqueous acetonitrile in the presence of oxygen was investigated: the corresponding sulfonic acids are produced in good yields for short alkyl chain compounds, together with smaller amounts of sulfuric and carboxylic acids. In acetonitrile, the influence of added water on the reaction course is evidenced: increased reaction rate and acid yields, control of sulfuric acid formation. Intermediates such as sulfinic acid and thiosulfonate were detected and their rates of formation were monitored. The reaction appears to involve thiyl radicals giving rise to sulfonyl radicals in the presence of oxygen. A first tentative hypothesis concerning the mechanism is advanced.