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Key Documents

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:
Molecular Weight:
70.09
Beilstein:
3592983
EC Number:
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.23

Quality Level

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.

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Storage Class Code

4.1B - Flammable solid hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. What is Product 281018, Sodium Thiomethoxide, soluble in?

    Sodium Thiomethodixe is freely soluble in water or ethanol, but is practically insoluble in ether.

  4. What impurities are present in Product 281018, Sodium Thiomethoxide? 

    We have not performed impurity profiling on this product and therefore do not know what the impurities could be.  Typical impurities would be unreacted starting materials, residual solvents, reaction byproducts, etc.  We also note that there may some residual methanol present in the material.

  5. What is Product 281018, Sodium Thiomethoxide?

    Sodium Thiomethoxide is an intermediate for synthesis of s-methyl thioesters when reacted with activated carboxylates and methyl alkyl sulfides when reacted with alkyl halides or tosylates.  (S. Patai, ed., The Chemistry of the Thiol Group, vol. I and II, Wiley, New York, 1974)(T.C.Bruice in Organic Sulfur Compounds, N. Kharasch, ed., Pergamon Press, New York, 1961, p. 421)

  6. My bottle of Product 281018, Sodium Thiomethoxide, is tightly sealed, but it is still giving off a strong thiol smell.  Is that normal?

    Yes.  Many thiols are characterized by strong and repulsive odors which can "cling" to bottle during the packaging process or to clothes during use.  Storing the material in a well ventilated area should help to reduce the presence of the thiol odor.

  7. What type of reactions can Product 281018, Sodium Thiomethoxide, be used for?

    Sodium Thiomethoxide can be used in reactions as a strong nucleophile, for the deacetylation of esters to acid and of lactones to omega-(methylthio) acids, dealkylation of aryl methyl esters to phenols, and for the substitution of aryl halogenides, espcially fluorides and chlorides.

  8. How do I find price and availability?

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  9. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  10. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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
High Dielectric Constant Sulfonyl-Containing Dipolar Glass Polymers with Enhanced Orientational Polarization
Zhu, Yu-Feng, et al.
Macromolecules, 51, 6257-6266 (2018)
Dialkylated dibenzotetrathienoacene derivative as semiconductor for organic field effect transistors
Xiaoxia Liu, et al.
Organic Electronics, 15, 156-161 (2014)
Synthetic Communications, 37, 409-409 (2007)
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)

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