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Ethane-1,2-dithiol

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1,2-Ethanedithiol
1,2-Ethanedithiol
Ball-and-stick model of ethane-1,2-dithiol
Space-filling model of ethane-1,2-dithiol
Names
IUPAC name Ethane-1,2-dithiol
Other names Dimercaptoethane
1,2-Ethanedithiol
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.958 Edit this at Wikidata
RTECS number
  • KI3325000
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2H6S2/c3-1-2-4/h3-4H,1-2H2Key: VYMPLPIFKRHAAC-UHFFFAOYSA-N
  • InChI=1/C2H6S2/c3-1-2-4/h3-4H,1-2H2Key: VYMPLPIFKRHAAC-UHFFFAOYAA
SMILES
  • SCCS
Properties
Chemical formula C2H6S2
Molar mass 94.19 g·mol
Appearance Colorless liquid
Density 1.123 g/cm³
Melting point −41 °C (−42 °F; 232 K)
Boiling point 146 °C (295 °F; 419 K)
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
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability (yellow): no hazard codeSpecial hazards (white): no code
2 2
Flash point 50 °C
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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 commercially available. It can be prepared by the action of 1,2-dibromoethane on thiourea followed by hydrolysis.

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.

C2H4(SH)2 + RR'CO → C2H4S2CRR' + H2O
Protecting a carbonyl group by converting it to a 1,3-dithiolane, using 1,2-ethanedithiol
Protecting a carbonyl group by converting it to a 1,3-dithiolane, using 1,2-ethanedithiol

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.

References

  1. Speziale, A. J. (1963). "Ethanedithiol". Organic Syntheses; Collected Volumes, vol. 4, p. 401.
  2. R. E. Conrow "Ethanedithiol" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. doi:10.1002/047084289
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