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

Description

S-Methyl methanethiolsulfonate, also known as MMTS, is a light yellow liquid that is a sulfonic acid derivative obtained by condensation of methanesulfonic acid with methanethiol. It is known for its ability to rapidly and selectively modify sulfhydryl groups of enzymes and is useful for mapping the pore-lining regions of the ryanodine receptor.

Uses

Used in Enzyme Modification:
S-Methyl methanethiolsulfonate is used as a modifying agent for the sulfhydryl groups of enzymes, allowing for the alteration of enzyme properties and functions.
Used in Ryanodine Receptor Mapping:
In the field of biochemistry, S-Methyl methanethiolsulfonate is used as a mapping agent for the pore-lining regions of the ryanodine receptor, providing insights into the structure and function of this receptor.
Used as a Cross-linking Reagent:
S-Methyl methanethiolsulfonate serves as a carbonyl reactive homobifunctional cross-linking reagent that is cleavable with periodate, making it a valuable tool in various chemical and biological applications.
Used in Organic Synthesis:
As a sulfenylating agent, S-Methyl methanethiolsulfonate is utilized in the synthesis of β-keto sulfoxides, methylene compounds, half-esters of malonic acids, and aryl Grignard reagents, contributing to the development of new organic compounds.
Used in Protein Thiol-Disulfide State Trapping:
S-Methyl methanethiolsulfonate is employed as a reagent to trap the natural thiol-disulfide state of proteins, aiding in the study of protein structure, function, and stability.
General Description:
The interaction of S-methyl methanethiosulfonate (MMTS) with dipalmitoylphosphatidylcholine (DPPC) bilayers has been investigated using advanced spectroscopic techniques such as FTIR and surface-enhanced Raman spectroscopy, providing further understanding of its chemical properties and potential applications.

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

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

• 5813-48-9 Methanesulfenyl chloride 
• 624-92-0 Dimethyldisulphide 
• 13882-12-7 S-methyl methanethiosulfinate 
• 74-83-9 methyl bromide 
• 6340-98-3 potassium methanethiosulphonate 
• 18624-87-8 (α-chloro-benzyl)-methyl sulfide 
• 666-15-9 methyl methanesulfinate 
• 14094-11-2 tert-butyl methyl sulfoxide 
• 23413-69-6 α-Chlorbenzyliden-methyl-sulfoxid 
• 67-68-5 dimethyl sulfoxide 
• 2813-22-1 2-methanesulfinyl-1-phenyl-ethanone 
• 74-88-4 methyl iodide 
• 10265-92-6 Mio 
• 676-85-7 methylsulphinyl chloride 

Downstream Products

• 6543-74-4 bis-methanesulfonyl-methylsulfanyl-methane 
• 141869-55-8 ethyl α,α-bis(methylthio)phenylacetate 
• 40514-96-3 6β-benzylideneamino-6α-methylsulfanyl-penicillanic acid benzyl ester 
• 72873-48-4 C₈H₈S₃ 
• 58491-73-9 (6R)-7t-benzoylamino-3-methyl-2-methylsulfanyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2c-carboxylic acid methyl ester 
• 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 
• 66428-78-2 (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 
• 68474-75-9 (6R)-2-methylsulfanyl-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2c-carboxylic acid 2,2,2-trichloro-ethyl ester 
• 58482-81-8 (6R)-7t-benzoylamino-3-methyl-4c-methylsulfanyl-5t,8-dioxo-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid methyl ester 
• 58491-75-1 (6R)-7t-benzoylamino-3-methyl-7c-methylsulfanyl-5t,8-dioxo-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid methyl ester 
• 58482-80-7 (6R)-7t-benzoylamino-3-methyl-4,4-bis-methylsulfanyl-5t,8-dioxo-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid methyl ester 
• 58482-82-9 (6R)-7t-benzoylamino-3-methyl-4c,7c-bis-methylsulfanyl-5ξ,8-dioxo-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid methyl ester 
• 58482-79-4 (6R)-7t-benzoylamino-3-methyl-4,4,7c-tris-methylsulfanyl-5t,8-dioxo-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid methyl ester 

Relevant articles and documents

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