S-Methyl methanethiosulfonate

Base Information

• Chemical Name: S-Methyl methanethiosulfonate
• CAS No.: 2949-92-0
• Deprecated CAS: 117991-82-9,31761-75-8,31761-75-8
• Molecular Formula: C2H6 O2 S2
• Molecular Weight: 126.2
• Hs Code.: 2930909090
• European Community (EC) Number: 220-970-0
• NSC Number: 21545
• UNII: 0906Z2356U
• DSSTox Substance ID: DTXSID8062739
• Nikkaji Number: J149.996C
• Wikidata: Q27144634
• Metabolomics Workbench ID: 45138
• ChEMBL ID: CHEMBL1236925
• Mol file: 2949-92-0.mol

Synonyms:methyl methanesulfonothioate;methyl methanethiolsulfonate;methyl methanethiosulfonate;MMTS

Chemical Property of S-Methyl methanethiosulfonate

Chemical Property:

• Appearance/Colour: Light Yellow Liquid
• Vapor Pressure: 0.0138mmHg at 25°C
• Melting Point: 117.0-119.0 °C
• Refractive Index: n20/D 1.513(lit.)
• Boiling Point: 266.9 °C at 760 mmHg
• Flash Point: 87 ºC
• PSA: 67.82000
• Density: 1.337
• LogP: 1.38980
• Storage Temp.: 2-8°C
• Solubility.: chloroform: soluble750mg + 5 ml Chloroformmg/mL, colorless to li
• XLogP3: 0
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 125.98092178
• Heavy Atom Count: 6
• Complexity: 106

Purity/Quality:

99% ^*data from raw suppliers

Methylmethanethiolsulfonate 97% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi,Xn
• Statements: 36-36/37/38-20/21/22
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Sulfur Compounds
• Canonical SMILES: CSS(=O)(=O)C
• Uses: 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. carbonyl reactive homobifunctional cross-linking reagent cleavable with periodate 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.

Technology Process of S-Methyl methanethiosulfonate

There total 65 articles about S-Methyl methanethiosulfonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 12.0%

tert-butylethylene (558-37-2) + S-methyl methanethiosulfinate (13882-12-7) + trifluoroacetic anhydride (407-25-0) → methanethiosulfonic acid S-methyl ester (2949-92-0,31761-75-8) + Dimethyldisulphide (624-92-0) + methyl 3,3-dimethyl-1-trifluoroacetoxy-2-butyl sulfide (73682-79-8)

Guidance literature:

In tetrachloromethane; 1) -20 deg C, 2) up to rt;

DOI:10.1016/S0040-4020(01)98843-X

Reference yield: 7.1%

Dimethyldisulphide (624-92-0) → methanesulfonic acid (75-75-2,98527-29-8) + methanethiosulfonic acid S-methyl ester (2949-92-0,31761-75-8) + methyl bisulfate (75-93-4) + methyl methanesulfinate (666-15-9)

Guidance literature:

With oxygen; In methanol; at 30 - 40 ℃; for 9.5h; Irradiation; with Pyrex Filter;

DOI:10.1016/0040-4039(95)01698-H

Reference yield: 7.0%

S-methyl methanethiosulfinate (13882-12-7) + acetic anhydride (108-24-7) → methanethiosulfonic acid S-methyl ester (2949-92-0,31761-75-8) + Dimethyldisulphide (624-92-0) + 2,3,5-trithiahexane 5-oxide (42474-27-1) + acetylthiomethyl methyl sulphoxide (73975-52-7)

Guidance literature:

With acetic acid; at 90 ℃; for 2h;

DOI:10.1039/P29800000432

upstream raw materials:

Methanesulfenyl chloride

Dimethyldisulphide

S-methyl methanethiosulfinate

methyl bromide

Downstream raw materials:

(6R)-3-acetoxymethyl-2-methylsulfanyl-8-oxo-7t-tritylamino-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2t-carboxylic acid tert-butyl ester

ω-(Methylthio)-ω-(methylsulfinyl)-p-methoxyacetophenone

dimethyltrisulfane

(2R,3S)-3-methylsulfanylmethyl-1-(1-phenylethyl)-pyrrolidine-2-carboxylic acid benzyl ester

Refernces

• 1、 Laszlo, Pierre,Mathy, Arthur. "A Novel, Useful, and Inexpensive Preparation of S-Methyl Methanesulfonothioate". . p. 2281. Retrieved 1984.
• 2、 Huang, Shuai,Wang, Hao,Liu, Yongguo,Sun, Baoguo,Tian, Hongyu,Liang, Sen. "A novel practical preparation of methyl methanethiosulfonate from dimethyl sulfoxide initiated by a catalytic amount of (COCl)2 or anhydrous HCl". . p. 604 - 613. Retrieved 2021.
• 3、 Wen, Zhen-Kang,Liu, Xue-Hua,Liu, Yu-Fang,Chao, Jian-Bin. "Acid Promoted Direct Cross-Coupling of Methyl Ketones with Dimethyl Sulfoxide: Access to Ketoallyl Methylsulfides and -sulfones". . p. 5798 - 5801. Retrieved 2017.
• 4、 Kalaramna, Pratibha,Goswami, Avijit. "Temperature-Controlled Chemoselective Synthesis of Thiosulfonates and Thiocyanates: Novel Reactivity of KXCN (X=S, Se) towards Organosulfonyl Chlorides". supporting information. p. 5359 - 5366. Retrieved 2021/10/25.