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208795

Sigma-Aldrich

S-Methyl methanethiosulfonate

97%

Synonym(s):

S-Methyl thiomethanesulfonate, MMTS

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RM 226.00
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Estimated to ship on23 March 2025

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1 G
RM 226.00
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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

RM 226.00

Estimated to ship on23 March 2025

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Quality Level

200

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

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.[1] Interaction of S-methyl methanethiosulfonate (MMTS) with dipalmitoylphosphatidylcholine (DPPC) bilayers has been investigated by FTIR and surface-enhanced Raman spectroscopy[2].

Application

S-Methyl methanethiosulfonate was used as sulfenylating agent for β-keto sulfoxides[3], methylene compounds[4], half-esters of malonic acids[5] and aryl Grignard reagents[6]. It was also used as a reagent to trap the natural thiol-disulfide state of the proteins[7].

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ9486
BCCJ9487
BCCH3918
BCCG0900
BCCF9493

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Sustainable Three-Component Synthesis of Isothioureas from Isocyanides, Thiosulfonates, and Amines
P Mampuys, et al.
Angewandte Chemie (International Edition in English), 126 (2014)
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, 13063-13068 (2014)
The Journal of Organic Chemistry, 58, 6132-6132 (1993)
Journal of the Chemical Society. Perkin Transactions 1, 3167-3167 (1993)
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Questions

  1. What is the molarity of this reagent?

    1 answer

    1. The material is considered neat/pure (i.e. it is not a solution), so the molarity would be 10.59 molar, multiplied by whatever the lot-specific purity is, which can be found on the COA. The molarity value was determined by dividing the density by the molecular weight and correcting for units.

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