Sodium ethanethiolate
chemical compound
Sodium ethanethiolate is an organosulfur compound with the formula CH3CH2SNa. It is the sodium salt of the conjugate base of ethanethiol. This compound is commercially available as a white solid that is soluble in polar organic solvents. Sodium ethanethiolate is a reagent in organic synthesis. Hydrolysis of sodium ethanethiolate, e.g. in humid air, produces ethanethiol, which has a low odor threshold and a noxious "rotten egg" smell.
Preparation
Sodium ethanethiolate can be produced by treating a solution of ethanethiol with sodium hydride:
CH3CH2SH + NaH → CH3CH2SNa + H2
The closely related sodium methanethiolate can be 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 ethanethiolate is a source of ethanethiolate, a powerful nucleophile.
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