Ethyl xanthic acid

Ethyl xanthic acid is an organic compound with the chemical formula CH3CH2OCS2H. It can be viewed as an O-ethyl ester of dithiocarbonic O,S-acid (the formula of that acid is S=C(OH)(SH)). Ethyl xanthic acid belongs to the category of thioacids, where the prefix thio- means that an oxygen atom in the compound is replaced by a sulfur atom.

Ethyl xanthic acid
Ethyl xanthic acid molecule
Names
IUPAC name
Ethoxymethanedithioic acid[1]
Other names
  • Carbonodithioic acid, O-ethyl ester[1]
  • Ethyl xanthic acid
  • Ethylxanthate[1]
  • Ethylxanthic acid[1]
  • Ethylxanthogenic acid[1]
  • O-Ethyl hydrogen carbonodithioate[1]
  • O-Ethyl dithiocarbonic acid[1]
  • Xanthogenic acid[1]
Identifiers
3D model (JSmol)
EC Number
UNII
  • InChI=1S/C3H6OS2/c1-2-4-3(5)6/h2H2,1H3,(H,5,6)[1]
  • CCOC(=S)S
Properties
CH3CH2OCS2H
Molar mass 122.20 g·mol−1
Appearance Colorless oily liquid[2][1]
Melting point −53 °C (−63 °F; 220 K)
Boiling point Decomposes
Slightly[1]
Acidity (pKa) 1.6[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Preparation

Ethyl xanthic acid is obtained by the action of dilute sulphuric acid on potassium ethyl xanthate at 0 °C.[4]

Properties

Ethyl xanthic acid is a colorless unstable oily liquid.[2] It decomposes above 25 °C (77 °F) into carbon disulfide and ethanol.[1][4]

Esters of ethyl xanthic acid
Methyl ethylxanthate or O-ethyl S-methyl dithiocarbonate, a methyl ester of ethyl xanthic acid
Ethyl ethylxanthate or O,S-diethyl dithiocarbonate, an ethyl ester of ethyl xanthic acid

The methyl and ethyl esters of ethyl xanthic acid are colorless, oily liquids with a penetrating odor.[5]

Reactions

Ethyl xanthic acid reacts with water or moisture producing carbon disulfide.[1]

Safety

In an experiment with white rats, chronically exposed rats by inhalation of ethyl xanthic acid revealed higher frequency of chromosomal rearrangements in lymphocytes of peripheral blood than the control rats.[1]

References
  1. "Ethylxanthate". PubChem.
  2. "Xanthic acid". merriam-webster.com.
  3. Millican, Robert J.; Sauers, Carol K. (1979). "General acid-catalyzed decomposition of alkyl xanthates". The Journal of Organic Chemistry. 44 (10): 1664–1669. doi:10.1021/jo01324a018.
  4. "Xanthic Acid" . Encyclopædia Britannica. Vol. 28 (11th ed.). 1911. p. 881.
  5. "Xanthic acid". dictionary.com.
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