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Ethyl xanthic acid

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Chemical compound
Ethyl xanthic acid
Ethyl xanthic acid molecule
Names
IUPAC name Ethoxymethanedithioic acid
Other names
  • Carbonodithioic acid, O-ethyl ester
  • Ethyl xanthic acid
  • Ethylxanthate
  • Ethylxanthic acid
  • Ethylxanthogenic acid
  • O-Ethyl hydrogen carbonodithioate
  • O-Ethyl dithiocarbonic acid
  • Xanthogenic acid
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
EC Number
  • 205-780-8
PubChem CID
UNII
InChI
  • InChI=1S/C3H6OS2/c1-2-4-3(5)6/h2H2,1H3,(H,5,6)
SMILES
  • CCOC(=S)S
Properties
Chemical formula CH3CH2OCS2H
Molar mass 122.20 g·mol
Appearance Colorless oily liquid
Melting point −53 °C (−63 °F; 220 K)
Boiling point Decomposes
Solubility in water Slightly
Acidity (pKa) 1.6
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Ethyl xanthic acid is an organic compound with the chemical formula CH3CH2−O−C(=S)−SH. 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.

Preparation

Ethyl xanthic acid is obtained by the action of dilute sulfuric acid on potassium ethyl xanthate at 0 °C.


Ethyl xanthic acid is a colorless, labile oil. In aqueous solution, it decomposes rapidly by a unimolecular pathway to give carbon disulfide and ethanol.

Esters of ethyl xanthic acid

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

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

Reactions

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

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.

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. Iwasaki, Iwao; Cooke, Strathmore R. B. (1958). "The Decomposition of Xanthate in Acid Solution". Journal of the American Chemical Society. 80 (2): 285–288. Bibcode:1958JAChS..80..285I. doi:10.1021/ja01535a008.
  6. "Xanthic acid". dictionary.com.
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