2949-92-0

Basic information

• Product Name: S-Methyl methanethiolsulfonate
• Synonyms: S-Methyl thiomethanesuphonate;5-METHYLMETHANETHIONSULFONATE;4-methyl-2-amino-1,3-thiazole;Methanethiosulfonylmethyl;Methyl(methylsulfonyl) sulfide;Methyl(methylthio) sulfone;S-Methyl methanethiolsulfonate,97%;S-Methyl methanethiosulfonate,S-Methyl thiomethanesulfonate, MMTS
• CAS NO: 2949-92-0
• Molecular Formula: C₂H₆O₂S₂
• Molecular Weight: 126.2
• EINECS: 220-970-0
• Product Categories: Small molecule;MTS and Sulfhydryl Active Reagents;Sulfur Compounds (for Synthesis);Synthetic Organic Chemistry;MTS & Sulfhydryl Active Reagents
• Mol File: 2949-92-0.mol
• Article Data: 59

Chemical Properties

• Melting Point: 117.0-119.0 °C
• Boiling Point: 69-71 °C0.4 mm Hg(lit.)
• Flash Point: 190 °F
• Appearance: Light Yellow Liquid
• Density: 1.337 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0138mmHg at 25°C
• Refractive Index: n20/D 1.513(lit.)
• Storage Temp.: 2-8°C
• Solubility: chloroform: soluble750mg + 5 ml Chloroformmg/mL, colorless to li
• Stability: Water Sensitive
• BRN: 1446059
• CAS DataBase Reference: S-Methyl methanethiolsulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: S-Methyl methanethiolsulfonate(2949-92-0)
• EPA Substance Registry System: S-Methyl methanethiolsulfonate(2949-92-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36-36/37/38-20/21/22
• Safety Statements: 26-36/37/39
• RIDADR: 3334
• WGK Germany: 2
• RTECS: PB2765000
• F: 13
• HazardClass: IRRITANT
• PackingGroup: III
• Hazardous Substances Data: 2949-92-0(Hazardous Substances Data)

Usage

Chemical Properties

Light Yellow Liquid

Uses

Different sources of media describe the Uses of 2949-92-0 differently. You can refer to the following data:
1. S-Methyl methanethiolsulfonate is used for the rapid and selective modification of sulfhydryl groups of enzymes and it is also useful for mapping the pore-lining regions of the ryanodine receptor.
2. carbonyl reactive homobifunctional cross-linking reagent cleavable with periodate
3. S-Methyl methanethiosulfonate was used as sulfenylating agent for β-keto sulfoxides, methylene compounds, half-esters of malonic acids and aryl Grignard reagents. It was also used as a reagent to trap the natural thiol-disulfide state of the proteins.

Definition

ChEBI: A sulfonic acid derivative obtained by condensaton of methanesulfonic acid with methanethiol.

Synthesis Reference(s)

The Journal of Organic Chemistry, 49, p. 2281, 1984 DOI: 10.1021/jo00186a039Synthetic Communications, 20, p. 365, 1990 DOI: 10.1080/00397919008052777

General Description

Interaction of S-methyl methanethiosulfonate (MMTS) with dipalmitoylphosphatidylcholine (DPPC) bilayers has been investigated by FTIR and surface-enhanced Raman spectroscopy.

Purification Methods

Purify it by fractional distillation under reduced pressure, IR: 1350, 750 cm-1 . [Applegate et al. J Org Chem 38 943 1973, Beilstein 4 IV 31.]

InChI:InChI=1/C2H6O2S2/c1-5-6(2,3)4/h1-2H3

Upstream product

• 18624-87-8 (α-chloro-benzyl)-methyl sulfide 
• 67-68-5 dimethyl sulfoxide 
• 676-85-7 methylsulphinyl chloride 
• 13882-12-7 S-methyl methanethiosulfinate 
• 53135-87-8 hexachloro-inden-1-one 
• 2514-52-5 perchloro-2-cyclopentene-1-one 
• 2863-45-8 benzhydryl methyl sulfoxide 
• 93-58-3 benzoic acid methyl ester 
• 5418-86-0 tris(methylthio)methane 
• 624-92-0 Dimethyldisulphide 
• 74-86-2 acetylene 
• 10028-15-6 ozone 
• 378784-00-0 rhodium 
• 594-27-4 tetramethylstannane 

Downstream Products

• 6543-74-4 bis-methanesulfonyl-methylsulfanyl-methane 
• 68538-92-1 (6R)-7t-(methoxy-phenyl-methyleneamino)-3-methyl-2-methylsulfanyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2c-carboxylic acid 2,2,2-trichloro-ethyl ester 
• 68538-91-0 (6R)-3-acetoxymethyl-7t-(methoxy-phenyl-methyleneamino)-2-methylsulfanyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2c-carboxylic acid tert-butyl ester 
• 134950-45-1 [(E)-2-Amino-2-(4-chloro-phenyl)-1-methylsulfanyl-vinyl]-phosphonic acid diethyl ester 
• 532-32-1 sodium benzoate 
• 118721-49-6 1-(methylthio)-1-[(4-methylphenyl)sulfonyl]ethene 
• 100-68-5 methyl-phenyl-thioether 
• 55163-92-3 methanesulfinic acid; lithium salt 
• 52922-65-3 ω-(Methylthio)-ω-(methylsulfinyl)acetophenone 
• 3658-80-8 dimethyltrisulfane 
• 193538-85-1 (2R,3S)-3-methylsulfanylmethyl-1-(1-phenylethyl)-pyrrolidine-2-carboxylic acid benzyl ester 
• 193538-84-0 (2S,3R)-3-methylsulfanylmethyl-1-(1-phenylethyl)-pyrrolidine-2-carboxylic acid ethyl ester 
• 661-38-1 trichloro-methyl-λ⁴-sulfane 
• 124-63-0 methanesulfonyl chloride 

Relevant articles and documents

Preoxidation-assisted nitrogen enrichment strategy to decorate porous carbon spheres for catalytic adsorption/oxidation of methyl mercaptan

Porous carbon spheres with high surface area and microporous structure were synthesized from alkyl phenols and formaldehyde via suspension polymerization and steam activation. The effects of air oxidation and ammonia solution heat treatment on the pore structure and surface chemistry of the carbon spheres were studied for catalytic oxidation of CH3SH. The structure property and surface chemistry of the obtained carbon spheres were characterized by N2 adsorption-desorption, FTIR, scanning electron microscopy, XRD, elemental analysis, X-ray photoelectron spectroscopy and Boehm titration, and then thermal analysis and gas chromatography-mass spectrometry were applied to investigate the catalytic oxidation product. Results show that the as-prepared microporous carbon spheres through direct ammonia treatment have a high surface area value of 1710 m2 g-1 and a total pore volume of 0.83 cm3 g-1. Moreover, the preoxidation-assisted nitrogen enrichment strategy not only increases the surface area and total pore volume of the carbon spheres, but also introduces more active nitrogen species such as pyridinic nitrogen and quaternary nitrogen, leading to the highest nitrogen content of 7.13 wt% and the highest CH3SH capacity of 622.8 mg g-1 due to the pyridinic nitrogen and quaternary nitrogen as function of catalysts. In addition, water and oxygen have a beneficial effect on CH3SH oxidation over the nitrogen modified carbon spheres, and the basic oxidation product is CH3SSCH3 that can be further oxidized into CH3SO2SCH3 according to DTG and GC/MS analysis. The great recycling stability after ten cycles with a reserved CH3SH capacity of 97% demonstrates that the porous carbon spheres obtained by preoxidation-assisted enriched nitrogen strategy are promising for catalytic oxidation of CH3SH. This journal is

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Sulforaphane (SFN) and erucin (ERN) are isothiocyanates (ITCs) bearing, respectively, methylsulfinyl and methylsulfanyl groups. Their chemopreventive and anticancer activity is attributed to ability to modulate cellular redox status due to induction of Phase 2 cytoprotective enzymes (indirect antioxidant action) but many attempts to connect the bioactivity of ITCs with their radical trapping activity failed. Both ITCs are evolved from their glucosinolates during food processing of Cruciferous vegetables, therefore, we studied antioxidant behaviour of SFN/ERN at elevated temperature in two lipid systems. Neither ERN nor SFN inhibit the oxidation of bulk linolenic acid (below 100 °C) but both ITCs increase oxidative stability of soy lecithin (above 150 °C). On the basis of GC-MS analysis we verified our preliminary hypothesis (Antioxidants 2020, 9, 1090) about participation of sulfenic acids and methylsulfinyl radicals as radical trapping agents responsible for the antioxidant effect of edible ITCs during thermal oxidation of lipids at elevated temperatures (above 140 °C).

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