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Ethane-1,2-dithiol

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This is an old revision of this page, as edited by Emeldir (talk | contribs) at 15:32, 16 September 2016 (preferred IUPAC name (PIN) according to ''Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book)''). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

1,2-Ethanedithiol
1,2-Ethanedithiol
Ball-and-stick model of ethane-1,2-dithiol
Space-filling model of 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 Edit this at Wikidata
RTECS number
  • KI3325000
UNII
  • InChI=1S/C2H6S2/c3-1-2-4/h3-4H,1-2H2 checkY
    Key: VYMPLPIFKRHAAC-UHFFFAOYSA-N checkY
  • InChI=1/C2H6S2/c3-1-2-4/h3-4H,1-2H2
    Key: VYMPLPIFKRHAAC-UHFFFAOYAA
  • SCCS
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
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 (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).
checkY verify (what is checkY☒N ?)

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 prepared 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.[1]

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]

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-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.

See also

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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