Sodium methanethiolate or sodium thiomethoxide is an organosulfur compound with the formula CH3SNa. It is the sodium salt of the conjugate base of methanethiol. This compound is commercially available as a white solid that is soluble in polar organic solvents. Sodium methanethiolate is a reagent in organic synthesis and a byproduct of some industrial processes. Hydrolysis of sodium methanethiolate, e.g. in humid air, produces methanethiol, which has a low odor threshold and a noxious "rotten egg" smell.
Preparation Sodium methanethiolate can be produced by treating a solution of methanethiol in an etherial solvent with sodium hydride:
CH3SH + NaH → CH3SNa + H2 It is also prepared and used in situ (i.e., without isolation) by treatment of a solution of methanethiol with strong base such as sodium hydroxide.
Reactions Sodium methanethiolate is a source of methanethiolate, a powerful nucleophile. It is used to cleave methoxy-aryl ethers:
NaSCH3 + Ar−O−CH3 → Ar−ONa + CH3SCH3 (Ar = aryl) It converts alkyl halides to methyl thioethers:
NaSCH3 + RX → RSCH3 + NaX (X = halogen, R = alkyl) Oxidation of sodium methanethiolate gives dimethyldisulfide:
2 NaSCH3 + I2 → CH3SSCH3 + 2 NaI
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