Ethane-1,2-dithiol
| |
| |
| |
| Names | |
|---|---|
| Preferred IUPAC name
Ethane-1,2-dithiol | |
| Other names
Dimercaptoethane
1,2-Ethanedithiol | |
| Identifiers | |
3D model (JSmol)
|
|
| ChemSpider | |
| ECHA InfoCard | 100.007.958 |
| EC Number |
|
PubChem CID
|
|
| RTECS number |
|
| UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
| 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 |
Refractive index (nD)
|
1.5589 (D-line, 25 °C) |
| Hazards | |
| GHS labelling: | |
  
| |
| Danger | |
| H226, H301, H302, H310, H312, H319, H330 | |
| P210, P233, P240, P241, P242, P243, P260, P262, P264, P270, P271, P280, P284, P301 P310, P301 P312, P302 P350, P302 P352, P303 P361 P353, P304 P340, P305 P351 P338, P310, P312, P320, P321, P322, P330, P337 P313, P361, P363, P370 P378, P403 P233, P403 P235, P405, P501 | |
| NFPA 704 (fire diamond) | |
| Flash point | 50 °C (122 °F; 323 K) |
| Related compounds | |
Related thiols
|
1,1-Ethanedithiol; Ethanethiol; 1,3-Propanedithiol; 1,2-Benzenedithiol; Thiophenol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
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
[edit]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]
Applications
[edit]As a 1,2-dithiol, this compound is widely used in organic chemistry because it reacts with aldehydes and ketones to give 1,3-dithiolanes, which are useful intermediates. [3]
- 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-dioxolanes 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.
1,2-Ethanedithiol is commonly used as a scavenger in peptide cleavage synthesis.
See also
[edit]References
[edit]- ^ Choi, H.; Aldrich, J.v. (1993-07-01). "Comparison of methods for the Fmoc solid-phase synthesis and cleavage of a peptide containing both tryptophan and arginine". International Journal of Peptide and Protein Research. 42 (1): 58–63. doi:10.1111/j.1399-3011.1993.tb00350.x. ISSN 1399-3011. PMID 8103765.
- ^ Speziale, A. J. (1963). "Ethanedithiol". Organic Syntheses; Collected Volumes, vol. 4, p. 401.
- ^ R. E. Conrow "Ethanedithiol" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. doi:10.1002/047084289X