Ethyl xanthic acid

{{Short description|Chemical compound}}

{{Chembox

| IUPACName = Ethoxymethanedithioic acid{{Cite web | url = https://pubchem.ncbi.nlm.nih.gov/compound/Ethylxanthate | title = Ethylxanthate | work = PubChem }}

| OtherNames = {{ubl|Carbonodithioic acid, O-ethyl ester|Ethyl xanthic acid|Ethylxanthate|Ethylxanthic acid|Ethylxanthogenic acid|O-Ethyl hydrogen carbonodithioate|O-Ethyl dithiocarbonic acid|Xanthogenic acid}}

| ImageFile = Ethyl xanthic acid.png

| ImageAlt = Ethyl xanthic acid molecule

| Section1 = {{Chembox Identifiers

| CASNo = 151-01-9

| CASNo_Ref = {{Cascite|correct|CAS}}

| ChEMBL = 3039661

| ChemSpiderID = 8492

| EC_number = 205-780-8

| EC_number_Comment =

| InChI = 1S/C3H6OS2/c1-2-4-3(5)6/h2H2,1H3,(H,5,6)

| UNII = B7B55M6MK1

| UNII_Comment =

| PubChem = 8823

| SMILES = CCOC(=S)S

}}

| Section2 = {{Chembox Properties

| AtmosphericOHRateConstant =

| Appearance = Colorless oily liquid{{cite web | url = https://www.merriam-webster.com/dictionary/xanthic%20acid | title = Xanthic acid | website = merriam-webster.com }}

| BoilingPt = Decomposes

| Formula = {{chem2|CH3CH2OCS2H}}

| C=3|H=6|O=1|S=2

| MeltingPtC = −53

| pKa = 1.6{{cite journal |doi=10.1021/jo01324a018|title=General acid-catalyzed decomposition of alkyl xanthates |year=1979 |last1=Millican |first1=Robert J. |last2=Sauers |first2=Carol K. |journal=The Journal of Organic Chemistry |volume=44 |issue=10 |pages=1664–1669 }}

| Solubility = Slightly

}}

}}

Ethyl xanthic acid is an organic compound with the chemical formula {{chem2|CH3CH2\sO\sC(\dS)\sSH}}. It can be viewed as an O-ethyl ester of dithiocarbonic O,S-acid (the formula of that acid is {{chem2|S\dC(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.{{Cite EB1911|wstitle= Xanthic Acid | volume= 28 | page = 881 |short= 1}}

Ethyl xanthic acid is a colorless, labile oil. In aqueous solution, it decomposes rapidly by a unimolecular pathway to give carbon disulfide and ethanol.{{cite journal |doi=10.1021/ja01535a008 |title=The Decomposition of Xanthate in Acid Solution |date=1958 |last1=Iwasaki |first1=Iwao |last2=Cooke |first2=Strathmore R. B. |journal=Journal of the American Chemical Society |volume=80 |issue=2 |pages=285–288 |bibcode=1958JAChS..80..285I }}

Esters of ethyl xanthic acid

The methyl and ethyl esters of ethyl xanthic acid are colorless, oily liquids with a penetrating odor.{{cite web | title = Xanthic acid | url = https://www.dictionary.com/browse/xanthic-acid | website = dictionary.com}}

{{Multiple image

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| align = left

| image1 = Methyl ethylxanthate.png

| caption1 = Methyl ethylxanthate or O-ethyl S-methyl dithiocarbonate, a methyl ester of ethyl xanthic acid

| image2 = Ethyl ethylxanthate.png

| width2 =

| caption2 = Ethyl ethylxanthate or O,S-diethyl dithiocarbonate, an ethyl ester of ethyl xanthic acid

}}{{clear-left}}

Reactions

Ethyl xanthic acid reacts with water or moisture producing carbon disulfide.{{cln|Reaction equation please!|date=February 2023}}

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