5188-07-8

Sodium methanethiolate or sodium thiomethoxide (CH3SNa, MeSNa) is the sodium conjugate base of methanethiol. This compound is commercially available as a white solid. Sodium Methanethiolate is used as a nucleophile in organic synthesis. This compound is also being used as a reagent to synthesize thiol-based suberoylanilide hydroxamic acid (SAHA) analogues, compounds that act as potent histone deacetylase inhibitors. It reacts with trifluoroacetic acid and water to produce the active form of sodium trifluoroacetate. The reaction mechanism is likely due to the formation of a bicyclic heterocycle that has been shown to be effective against a number of bacteria.

Very faint yellowish red clear liquid

Sodium thiomethoxide is a strong nucleophile used for the synthesis of methyl aryl sulfides from halo-arenes. Alkanethiolates are efficient reagents for SN2 dealkylation of esters and aryl ethers.

Sodium thiomethoxide is a powerful nucleophile that can be used to prepare methylthioether and other organic compounds like ethyl bromide. Its hydrolysis in moist air produces methanethiol, which has a low odor threshold and a noxious fecal smell.

core: sodium

Sodium thiomethoxide is prepared by reacting sodium with 2-propanol under a nitrogen atmosphere, followed by the introduction of methyl mercaptan, solvent removal, and washing with anhydrous ethyl ether; isotopomers can also be generated in situ from S-methylisothiourea salts[1][2].

Dissolve the salt (10g) in EtOH (10mL) and add Et2O (100mL). Cool and collect the precipitate, wash it with Et2O and dry it in a vacuum. It is a white powder which is very soluble in EtOH and H2O. [Billmann & Jensen Bull Soc Chim Fr 3 2318 1936, Beilstein 1 III 1212.]

[1]Kornblum, N., Carlson, S. C., & Smith, R. G. (1979). Substitution reactions which proceed via radical anion intermediates. 20. Replacement of the nitro group by hydrogen. Journal of the American Chemical Society, 101(3), 647–657. https://doi.org/10.1021/ja00497a028
[2]Mohamed, A. H., Ballantine, R. D., Shen, L., Mouhsine, B., Chenon, M., Robert, V., Pifferi, C., Beltramo, M., Alami, M., Audisio, D., Aucagne, V., & Messaoudi, S. (2026). Rapid Methylthiolation of (Hetero)Aryl Halides at Room Temperature Using Sodium Thiomethoxide via Palladium‐Catalysis. Chemistry – A European Journal, 32(25). https://doi.org/10.1002/chem.71032