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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:
Molecular Weight:
126.20
Beilstein:
1446059
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
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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Synthetic Communications, 22, 1359-1359 (1992)
Sustainable Three-Component Synthesis of Isothioureas from Isocyanides, Thiosulfonates, and Amines
P Mampuys, et al.
Angewandte Chemie (International Edition in English), 126 (2014)
Journal of the Chemical Society. Perkin Transactions 1, 3167-3167 (1993)
Anna-Riikka Karala et al.
Antioxidants & redox signaling, 9(4), 527-531 (2007-02-07)
S-Methyl methanethiosulfonate (MMTS) is a reagent used to trap the natural thiol-disulfide state of the proteins. The efficiency of trapping mixed disulfides in vivo has been found to be higher for MMTS than for the more commonly used N-ethylmaleimide. MMTS
The Journal of Organic Chemistry, 58, 6132-6132 (1993)

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