1,2-Ethanedithiol
From Wikipedia, the free encyclopedia
| 1,2-Ethanedithiol | |
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| IUPAC name | Ethane-1,2-dithiol |
| Other names | Dimercaptoethane 1,2-Ethanedithiol |
| Identifiers | |
| CAS number | [540-63-6] |
| RTECS number | KI3325000 |
| SMILES | SCCS |
| Properties | |
| Molecular formula | C2H6S2 |
| Molar mass | 94.20 g/mol |
| Appearance | Colorless liquid |
| Density | 1.123 g/cm³, liquid |
| Melting point |
-41 °C |
| Boiling point |
146 °C |
| Solubility in water | Slightly sol |
| Solubility in other solvents | Good solubility in most organic solvents |
| Acidity (pKa) | ~11 |
| Refractive index (nD) | 1.5589 (D-line, 25 °C) |
| Hazards | |
| EU classification | Toxic (T) |
| NFPA 704 |
 2
2
0
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| R-phrases | R10 R22 |
| S-phrases | S16 |
| Flash point | 50 °C |
| 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.
[edit] Preparation
1,2-Ethanedithiol is commercially available. It can be prepared by the action of 1,2-dibromoethane on thiourea followed by hydrolysis.[1]
[edit] 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.
[edit] References
- ^ Speziale, A. J. (1963). "Ethanedithiol". Org. Synth.; Coll. Vol. 4: 401.
- ^ R. E. Conrow "Ethanedithiol" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. DOI: 10.1002/047084289.
