1,2-Ethanedithiol

1,2-Ethanedithiol
Names
IUPAC name
Ethane-1,2-dithiol
Other names
Dimercaptoethane
1,2-Ethanedithiol
Identifiers
540-63-6 YesY
ChemSpider 13865015 YesY
Jmol interactive 3D Image
RTECS number KI3325000
UNII 92T634FLAR YesY
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
Toxic (T)
R-phrases R10 R22
S-phrases S16
NFPA 704
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 fuel Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity (yellow): no hazard code Special 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

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

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.

See also

References

  1. Speziale, A. J. (1963). "Ethanedithiol". Org. Synth.; Coll. 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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