Ethyl xanthic acid

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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).

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[edit]

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

Properties[edit]

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[edit]

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

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

Reactions[edit]

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

Safety[edit]

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[edit]

  1. ^ a b c d e f g h i j k l m n o p "Ethylxanthate". PubChem.
  2. ^ a b "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. ^ a b "Xanthic Acid" . Encyclopædia Britannica. Vol. 28 (11th ed.). 1911. p. 881.
  5. ^ "Xanthic acid". dictionary.com.
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