Ethyl xanthic acid

Ethyl xanthic acid
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	151-01-9 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL3039661;
ChemSpider	8492;
EC Number	205-780-8 ;
PubChem CID	8823;
UNII	B7B55M6MK1 ;
	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−1
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 [77 °F], 100 kPa). Infobox references

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.^[4]

Ethyl xanthic acid is a colorless, labile oil. In aqueous solution, it decomposes rapidly by a unimolecular pathway to give carbon disulfide and ethanol.^[1]^[4]^[5]

Esters of ethyl xanthic acid

The methyl and ethyl esters of ethyl xanthic acid are colorless, oily liquids with a penetrating odor.^[6]

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

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

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

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

[pubchem-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p "Ethylxanthate". PubChem.

[merriam-webster-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.

[wikisource-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.

[dictionary-6] "Xanthic acid". dictionary.com.

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