1,2-Ethanedithiol is a colorless liquid with the formula C2H4(SH)2. It has a very characteristic odor which is compared by many people to rotten cabbage. It is a common building block in organic synthesis and an excellent ligand for metal ions.
1,2-Ethanedithiol is prepared commercially by the reaction of 1,2-dichloroethane with aqueous sodium bisulfide. In the laboratory, it can also be prepared by the action of 1,2-dibromoethane on thiourea followed by hydrolysis.
This compound is widely used in organic chemistry because it reacts with aldehydes and ketones to give 1,3-dithiolanes, which are useful intermediates.
Other 1,2- and 1,3-dithiols undergo this reaction to give related 1,3-dithiolanes and 1,3-dithianes (six-membered rings). Diols such as ethylene glycol undergo analogous reactions to 1,3-dioxolanes and 1,3-dioxanes. One distinguishing feature of the dithiolanes and dithianes derived from aldehydes is that the methyne group can be deprotonated and the resulting carbanion alkylated.
1,2-Ethanedithiol is commonly used as a scavenger in peptide cleavage synthesis.