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281018

Sigma-Aldrich

Sodium thiomethoxide

95%

Synonym(s):

Sodium methanethiolate, Methanethiol sodium salt, Sodium thiomethoxide

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About This Item

Linear Formula:
CH3SNa
CAS Number:
5188-07-8
Molecular Weight:
70.09
Beilstein/REAXYS Number:
3592983
EC Number:
225-969-9
MDL number:
MFCD00174316
UNSPSC Code:
12352103
PubChem Substance ID:
24856962
NACRES:
NA.23

Quality Level

100

assay

95%

form

powder or crystals

reaction suitability

core: sodium

SMILES string

[Na+].C[S-]

InChI

1S/CH4S.Na/c1-2;/h2H,1H3;/q;+1/p-1

InChI key

RMBAVIFYHOYIFM-UHFFFAOYSA-M

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General description

Sodium thiomethoxide is mainly used as a reagent in organicsynthesis, especially as a strong nucleophile for various reactions such astransesterification reactions and condensation reactions. It is also asulfur source to prepare various inorganic and organosulfurcompounds.

Application

Sodium thiomethoxide can be used:
  • As a precursor to synthesize sulfonyl-containing dipolar glass polymers.
  • To fabricate semiconductors for organic field effect transistors.
  • To synthesize mono- and dithiols of tetraethylene glycol andpoly(ethylene glycol)s via transesterification reaction.

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Danger

Hazard Classifications

Acute Tox. 3 Oral - Flam. Sol. 1 - Skin Corr. 1A

Storage Class

4.1B - Flammable solid hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL9808
BCCJ9808
BCCK4698
BCCB9876
0000074738

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Synthesis of Mono-and Dithiols of Tetraethylene Glycol and Poly(ethylene glycol)s via Enzyme Catalysis
Prajakatta Mulay, et al.
Catalysts, 9, 228-228 (2019)
Synthetic Communications, 37, 409-409 (2007)
High Dielectric Constant Sulfonyl-Containing Dipolar Glass Polymers with Enhanced Orientational Polarization
Zhu, Yu-Feng, et al.
Macromolecules, 51, 6257-6266 (2018)
Kuhan Chandru et al.
Scientific reports, 6, 29883-29883 (2016-07-23)
Thioesters and thioacetic acid (TAA) have been invoked as key reagents for the origin of life as activated forms of acetate analogous to acetyl-CoA. These species could have served as high-energy group-transfer reagents and allowed carbon insertions to form higher
Zichao Ye et al.
Dalton transactions (Cambridge, England : 2003), 45(47), 18954-18966 (2016-11-16)
Approaching the ultimate limits of material sizes provides a route for designing new functional materials with extraordinary properties. We report the first systematic synthesis and characterization study of a wide range of highly ordered silver alkanethiolate (AgSCnH2n+1 or AgSCn, n
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