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Merck

208795

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24852530
EC Number:
220-970-0
Beilstein/REAXYS Number:
1446059
MDL number:
MFCD00007565
Assay:
97%
Form:
liquid

Key Documents

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InChI key

XYONNSVDNIRXKZ-UHFFFAOYSA-N

InChI

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

SMILES string

CSS(C)(=O)=O

assay

97%

form

liquid

Quality Level

200

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.)

functional group

disulfide

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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.

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301,H317

Hazard Classifications

Acute Tox. 3 Oral - Skin Sens. 1

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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ9487
BCCJ9486
BCCH3918
BCCG0900
BCCF9493

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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
Sustainable Three-Component Synthesis of Isothioureas from Isocyanides, Thiosulfonates, and Amines
P Mampuys, et al.
Angewandte Chemie (International Edition in English), 126, 13063-13068 (2014)
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