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208795

Sigma-Aldrich

S-Methyl methanethiosulfonate

97%

Synonym(s):

S-Methyl thiomethanesulfonate, MMTS

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About This Item

Linear Formula:
CH3SO2SCH3
CAS Number:
2949-92-0
Molecular Weight:
126.20
Beilstein:
1446059
EC Number:
220-970-0
MDL number:
MFCD00007565
UNSPSC Code:
12352100
PubChem Substance ID:
24852530
NACRES:
NA.22

Assay

97%

form

liquid

refractive index

n20/D 1.513 (lit.)

bp

69-71 °C/0.4 mmHg (lit.)

solubility

DMF: soluble 1:1
chloroform: soluble 200 ul per mL, clear, faintly yellow-green
water: soluble 1:5

density

1.337 g/mL at 25 °C (lit.)

SMILES string

CSS(C)(=O)=O

InChI

1S/C2H6O2S2/c1-5-6(2,3)4/h1-2H3

InChI key

XYONNSVDNIRXKZ-UHFFFAOYSA-N

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General description

S-Methyl methanethiosulfonate is a reagent used to synthesize thiols and thioesters. Used as cross-linking agent to prepare polymer networks. Interaction of S-methyl methanethiosulfonate (MMTS) with dipalmitoylphosphatidylcholine (DPPC) bilayers has been investigated by FTIR and surface-enhanced Raman spectroscopy.

Application

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.

Storage Class Code

10 - Combustible liquids

WGK

WGK 2

Flash Point(F)

188.6 °F - closed cup

Flash Point(C)

87 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Journal of the Chemical Society. Perkin Transactions 1, 3167-3167 (1993)
Sustainable Three-Component Synthesis of Isothioureas from Isocyanides, Thiosulfonates, and Amines
P Mampuys, et al.
Angewandte Chemie (International Edition in English), 126 (2014)
Felix Kopp et al.
Chemical communications (Cambridge, England), (20), 2075-2077 (2007-08-24)
The magnesiation of halogenated aromatic and heteroaromatic carboxylic acids is accomplished by their treatment with MeMgCl in the presence of LiCl and subsequent reaction with i-PrMgCl.LiCl; the resulting double-magnesiated species react with a variety of electrophiles in up to 97%
W H Briggs et al.
Journal of agricultural and food chemistry, 48(11), 5731-5735 (2000-11-23)
Thiosulfinates (TSs) have been implicated as a principle source of the antiplatelet property of raw onion and garlic juice. The in vitro responses of human platelets to dosages of four TSs were measured using whole blood aggregometry and compared by
María E Defonsi Lestard et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 97, 479-489 (2012-07-27)
The present study is a first step towards the investigation of S-methyl methanethiosulfonate (MMTS) interaction with membrane model systems like liposomes. In this paper, the interaction of MMTS with dipalmitoylphosphatidylcholine (DPPC) bilayers was studied by FTIR and SERS spectroscopy. Lysolipid
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