Ethane-1,2-dithiol

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Ethane-1,2-dithiol
Ethane-1,2-dithiol Ethanedithiol.png
Ethane-1,2-dithiol
Ball-and-stick model of ethane-1,2-dithiol Ethane-1,2-dithiol-3D-balls.png
Ball-and-stick model of ethane-1,2-dithiol
Space-filling model of ethane-1,2-dithiol Ethane-1,2-dithiol-3D-vdW.png
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-752-3
PubChem CID
RTECS number
  • KI3325000
UNII
  • InChI=1S/C2H6S2/c3-1-2-4/h3-4H,1-2H2 Yes check.svgY
    Key: VYMPLPIFKRHAAC-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C2H6S2/c3-1-2-4/h3-4H,1-2H2
    Key: VYMPLPIFKRHAAC-UHFFFAOYAA
  • SCCS
Properties
C2H6S2
Molar mass 94.19 g·mol−1
AppearanceColorless 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 solventsGood solubility in
most organic solvents
Acidity (pKa)≈11
1.5589 (D-line, 25 °C)
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-skull.svg GHS-pictogram-exclam.svg
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)
NFPA 704.svgHealth 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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Ethane-1,2-dithiol, also known as EDT, [1] is a colorless liquid with the formula C 2 H 4(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.

Contents

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]

Reactions

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]

Protecting a carbonyl group by converting it to a 1,3-dithiolane, using ethane-1,2-dithiol Carbonyl-protection-with-ethanedithiol-2D.png
Protecting a carbonyl group by converting it to a 1,3-dithiolane, using ethane-1,2-dithiol

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

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". 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 ; Collected Volumes, vol. 4, p. 401.
  3. ↑ 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.
  4. ↑ R. E. Conrow "Ethanedithiol" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. doi : 10.1002/047084289X
  5. ↑ 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.
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