Chemistry:Ethane-1,2-dithiol

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Ethane-1,2-dithiol
Ethane-1,2-dithiol
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
EC Number
  • 208-752-3
RTECS number
  • KI3325000
UNII
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
GHS pictograms GHS02: FlammableGHS06: ToxicGHS07: Harmful
GHS Signal word Danger
H226, H301, H302, H310, H312, H319, H330
P210, P233, P240, P241, P242, P243, P260, P262, P264, P270, P271, P280, P284, P301+310, P301+312, P302+350, P302+352, P303+361+353, P304+340, P305+351+338, P310, P312, P320, P321, P322
NFPA 704 (fire diamond)
Flammability code 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 fuelHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity (yellow): no hazard codeSpecial hazards (white): no codeNFPA 704 four-colored diamond
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).
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Infobox references
Tracking categories (test):

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

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

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
Protecting a carbonyl group by converting it to a 1,3-dithiolane, using ethane-1,2-dithiol

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

References

  1. ↑ 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" (in en). 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. 
  2. ↑ Speziale, A. J. (1963). "Ethanedithiol". Organic Syntheses. http://www.orgsyn.org/demo.aspx?prep=cv4p0401. ; Collective Volume, 4, pp. 401 
  3. ↑ R. E. Conrow "Ethanedithiol" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. doi:10.1002/047084289X



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