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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

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.)

functional group

disulfide

Quality Level

200

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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

10 - Combustible liquids

wgk

WGK 2

flash_point_f

188.6 °F - closed cup

flash_point_c

87 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ9487
BCCJ9486
BCCH3918
BCCG0900
BCCF9493

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Journal of the Chemical Society. Perkin Transactions 1, 3167-3167 (1993)
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)
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
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
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