1,2-Ethanedithiol
Encyclopedia
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.
on thiourea
followed by hydrolysis
.
s and ketone
s to give 1,3-dithiolane
s, 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). Diol
s such as ethylene glycol
undergo analogous reactions to 1,3-dioxalanes 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.
Organic synthesis
Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic molecules can often contain a higher level of complexity compared to purely inorganic compounds, so the synthesis of organic compounds has...
and an excellent ligand for metal ions.
Preparation
1,2-Ethanedithiol is commercially available. It can be prepared by the action of 1,2-dibromoethane1,2-Dibromoethane
1,2-Dibromoethane, also known as ethylene dibromide , is the chemical compound with the formula BrCH2CH2Br. Although trace amounts occur naturally in the ocean, where it is formed probably by algae and kelp, it is mainly a synthetic...
on thiourea
Thiourea
Thiourea is an organosulfur compound of with the formula SC2 . It is structurally similar to urea, except that the oxygen atom is replaced by a sulfur atom, but the properties of urea and thiourea differ significantly. Thiourea is a reagent in organic synthesis. "Thioureas" refers to a broad...
followed by hydrolysis
Hydrolysis
Hydrolysis is a chemical reaction during which molecules of water are split into hydrogen cations and hydroxide anions in the process of a chemical mechanism. It is the type of reaction that is used to break down certain polymers, especially those made by condensation polymerization...
.
Applications
This compound is widely used in organic chemistry because it reacts with aldehydeAldehyde
An aldehyde is an organic compound containing a formyl group. This functional group, with the structure R-CHO, consists of a carbonyl center bonded to hydrogen and an R group....
s and ketone
Ketone
In organic chemistry, a ketone is an organic compound with the structure RCR', where R and R' can be a variety of atoms and groups of atoms. It features a carbonyl group bonded to two other carbon atoms. Many ketones are known and many are of great importance in industry and in biology...
s to give 1,3-dithiolane
Dithiolane
A dithiolane is a sulfur heterocycle derived from cyclopentane by replacing two CH2 groups with thioether groups. The parent compounds are 1,2-dithiolane and 1,3-dithiolane.1,2-Dithiolanes, such as lipoic acid, are cyclic disulfides....
s, which are useful intermediates.
-
- C2H4(SH)2 + RR'CO → C2H4S2CRR' + H2O
Other 1,2- and 1,3-dithiols undergo this reaction to give related 1,3-dithiolanes and 1,3-dithianes (six-membered rings). Diol
Diol
A diol or glycol is a chemical compound containing two hydroxyl groups A geminal diol has two hydroxyl groups bonded to the same atom...
s such as ethylene glycol
Ethylene glycol
Ethylene glycol is an organic compound widely used as an automotive antifreeze and a precursor to polymers. In its pure form, it is an odorless, colorless, syrupy, sweet-tasting liquid...
undergo analogous reactions to 1,3-dioxalanes 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.