Sodium methanethiolate
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| Appearance | white[1] |
| Density | 1.43 g/cm3[2] |
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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[1] 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:
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.[3][4]
Reactions
Sodium methanethiolate is a source of methanethiolate, a powerful nucleophile. It is used to cleave methoxy-aryl ethers:[1]
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It converts alkyl halides to methyl thioethers:[5]
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Oxidation of sodium methanethiolate gives dimethyldisulfide:
References
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