Skip to Content
MilliporeSigma
All Photos(3)

Key Documents

View All Documentation

281018

Sigma-Aldrich

Sodium thiomethoxide

95%

Synonym(s):

Sodium methanethiolate, Methanethiol sodium salt, Sodium thiomethoxide

Sign Into View Organizational & Contract Pricing

Select a Size

1 G
$48.40
5 G
$129.00
25 G
$546.00

$48.40

In StockDetails

Request a Bulk Order
All Photos(3)

Select a Size

Change View
1 G
$48.40
5 G
$129.00
25 G
$546.00

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

$48.40

In StockDetails

Request a Bulk Order

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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.[1][2]

Application

Sodium thiomethoxide can be used:
  • As a precursor to synthesize sulfonyl-containing dipolar glass polymers.[1]
  • To fabricate semiconductors for organic field effect transistors.[2]
  • To synthesize mono- and dithiols of tetraethylene glycol andpoly(ethylene glycol)s via transesterification reaction.[3]

signalword

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCCL9808
BCCJ9808
BCCK4698
BCCB9876
0000074738

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Dialkylated dibenzotetrathienoacene derivative as semiconductor for organic field effect transistors
Xiaoxia Liu, et al.
Organic Electronics, 15, 156-161 (2014)
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
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)
View All Related Papers

Questions

1–8 of 8 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

      Helpful?

  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

      Helpful?

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

    1 answer

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

      Helpful?

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

    1 answer

    1. 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.

      Helpful?

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

    1 answer

    1. 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.

      Helpful?

  6. What is Product 281018, Sodium Thiomethoxide?

    1 answer

    1. 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)

      Helpful?

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

    1 answer

    1. 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.

      Helpful?

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

    1 answer

    1. 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.

      Helpful?

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service