Ethane-1,2-dithiol
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Names | |
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Preferred IUPAC name
Ethane-1,2-dithiol | |
Other names
Dimercaptoethane
1,2-Ethanedithiol | |
Identifiers | |
3D model (JSmol)
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ChemSpider | |
ECHA InfoCard | 100.007.958 |
EC Number |
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PubChem CID
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RTECS number |
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UNII | |
CompTox Dashboard (EPA)
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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 |
Refractive index (nD)
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1.5589 (D-line, 25 °C) |
Hazards | |
GHS labelling: | |
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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
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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).
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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
[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]
Reactions
[edit]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:
- (CH2SH)2 + 2 NR3 + R'I → (CH2SR')2 + 2 [R3NH]I
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.[citation needed]
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
[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.
- ^ Goodrow, Marvin H.; Olmstead, Marilyn M.; Musker, W.Kenneth (1982). "Preparation, Properties and Crystal Structure of 1,2,5,6-Tetrathiacyclooctane". Tetrahedron Letters. 23 (32): 3231–3234. doi:10.1016/S0040-4039(00)87577-2.
- ^ R. E. Conrow "Ethanedithiol" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. doi:10.1002/047084289X
- ^ Hogarth, Graeme (2023). "An Unexpected leading role for [Fe2(CO)6(μ-PDT)] in our Understanding of [FeFe]-H2ases and the Search for Clean Hydrogen Production". Coordination Chemistry Reviews. 490. doi:10.1016/j.ccr.2023.215174.