1,2-Ethanedithiol
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| 1,2-Ethanedithiol | |
|---|---|
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| General | |
| Systematic name | 1,2-Ethanedithiol |
| Other names | Dimercaptoethane |
| Molecular formula | C2H6S2 |
| SMILES | SCCS |
| Molar mass | 94.20 g/mol |
| Appearance | Colorless liquid |
| CAS number | [540-63-6] |
| Properties | |
| Density and phase | 1.123 g/cm³, liquid |
| Solubility in water | Slightly sol |
| Solubility in other solvents |
Good solubility in most organic solvents |
| Melting point | -41 °C |
| Boiling point | 146 °C 63 °C @46 mmHg |
| Acidity (pKa) | ~11 |
| Basicity (pKb) | ? |
| Viscosity | ? cP at ? °C |
| Structure | |
| Dipole moment | ? D |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | Stench |
| NFPA 704 |
2
2
0
|
| Flash point | 50 °C |
| R/S statement | R: R10 R22 S: S16 |
| RTECS number | KI3325000 |
| Supplementary data page | |
| Structure and properties |
n =1.5589 (D-line, 25 °C) |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Related compounds | |
| Related thiols | Ethanethiol 1,3-Propanedithiol 1,2-Benzenedithiol Thiophenol |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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1,2-Ethanedithiol is an odorous, colorless liquid with the formula C2H4(SH)2. It is a common building block in organic synthesis and an excellent ligand for metal ions.
Contents |
[edit] Applications in organic chemistry
It is widely used in organic chemistry because it reacts with aldehydes and ketones to give 1,3-dithiolanes, which are useful intermediates. [1]
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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 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.
[edit] Synthesis
It can be prepared by the action of 1,2-dibromoethane on thiourea followed by hydrolysis.[2]
[edit] References
- ^ R. E. Conrow "Ethanedithiol" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. DOI: 10.1002/047084289.
- ^ Speziale, A. J. "Ethanedithiol" Organic Syntheses, Collec Volume 4, p.401 (1963).
