Ethane-1,2-dithiol
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Template:Chembox image cellTemplate:Chembox image cellTemplate:Chembox image cellTemplate:Chembox AllOtherNamesTemplate:Chembox headerbarTemplate:Chembox IndexlistTemplate:Chembox JmolTemplate:Chembox ChEMBLTemplate:Chembox ECHATemplate:Chembox E numberTemplate:Chembox IUPHAR ligandTemplate:Chembox UNIITemplate:Chembox CompToxTemplate:Chembox headerbarTemplate:Chembox SolubilityInWaterTemplate:Chembox headerbarTemplate:Chembox GHS (set)Template:Chembox headerbarTemplate:Chembox Datapage checkTemplate:Chembox Footer| Template:Longitem | Template:Unbulleted list |
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| Molar mass | Template:Chem molar mass |
| Appearance | Colorless liquid |
| Density | 1.123 g/cm3 |
| Melting point | Template:Chembox CalcTemperatures |
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| Solubility in other solvents | Good solubility in most organic solvents |
| Acidity (pKa) | ≈11 |
| Template:Longitem | 1.5589 (D-line, 25 °C) |
| NFPA 704 (fire diamond) | Template:NFPA 704 diamond |
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| Template:Longitem | 1,1-Ethanedithiol; Ethanethiol; 1,3-Propanedithiol; 1,2-Benzenedithiol; Thiophenol |
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Ethane-1,2-dithiol, also known as EDT,[1] 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.
Preparation
Ethane-1,2-dithiol is made 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.[2]
Reactions
1,2-Ethanedithiol is a weak acid, typical of alkyl thiols. In the presence of base and an alkylating agent, 1,2-ethanedithiol converts to thioethers:
Oxidation of 1,2-ethanedithiol gives a series of oligomers, including the cyclic bis(disulfide).[3]
As a 1,2-dithiol, this compound reacts with aldehydes and ketones to give 1,3-dithiolanes, which can be useful intermediates.[4]
Other 1,2- and 1,3-dithiols give related 1,3-dithiolanes (five-membered) and 1,3-dithianes (six-membered rings). Diols such as ethylene glycol undergo analogous reactions to give 1,3-dioxolanes. 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 has been used as a scavenger in peptide cleavage synthesis.Script error: No such module "Unsubst".
Like 1,3-propanedithiol, 1,2-ethanedithiol readily forms metal thiolate complexes. Illustrative is the synthesis of the derivative diiron ethanedithiolate hexacarbonyl upon reaction with triiron dodecacarbonyl:[5]
- Fe3(CO)12 + C2H4(SH)2 → Fe2(S2C2H4)(CO)6 + H2 + Fe(CO)5 + CO
See also
References
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- ↑ R. E. Conrow "Ethanedithiol" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. Script error: No such module "CS1 identifiers".
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