Sodium ethanethiolate

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:
The closely related sodium methanethiolate can be prepared and used in situ 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. It is used to cleave methoxy-aryl ethers:
It converts alkyl halides to ethyl thioethers
Oxidation of sodium methanethiolate gives diethyldisulfide: