1,2-Ethanedithiol
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| Names | |
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| IUPAC name
Ethane-1,2-dithiol
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| Other names
Dimercaptoethane
1,2-Ethanedithiol |
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| Identifiers | |
540-63-6  |
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| ChemSpider | 13865015 |
| Jmol 3D model | Interactive image |
| RTECS number | KI3325000 |
| UNII | 92T634FLAR |
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| Properties | |
| C2H6S2 | |
| Molar mass | 94.19 g·mol−1 |
| Appearance | Colorless liquid |
| Density | 1.123 g/cm³ |
| Melting point | −41 °C (−42 °F; 232 K) |
| Boiling point | 146 °C (295 °F; 419 K) 46 mmHg |
| Slightly sol | |
| Solubility in other solvents | Good solubility in most organic solvents |
| Acidity (pKa) | ~11 |
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Refractive index (nD)
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1.5589 (D-line, 25 °C) |
| Vapor pressure | {{{value}}} |
| Related compounds | |
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Related thiols
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1,1-Ethanedithiol; Ethanethiol; 1,3-Propanedithiol; 1,2-Benzenedithiol; Thiophenol |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
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.
Preparation
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.[1]
Applications
This compound is widely used in organic chemistry because it reacts with aldehydes and ketones to give 1,3-dithiolanes, which are useful intermediates. [2]
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- 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). Diols 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.
See also
References
- ↑ Lua error in package.lua at line 80: module 'strict' not found.; Lua error in package.lua at line 80: module 'strict' not found.
- ↑ R. E. Conrow "Ethanedithiol" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. doi:10.1002/047084289
