{{Short description|Chemical compound C2H4(SH)2}} {{chembox |Watchedfields = changed |verifiedrevid = 477204496 |Name = Ethane-1,2-dithiol |ImageFile = Ethanedithiol.png |ImageSize = 150px |ImageName = Ethane-1,2-dithiol |ImageFile1 = Ethane-1,2-dithiol-3D-balls.png |ImageSize1 = 150px |ImageName1 = Ball-and-stick model of ethane-1,2-dithiol |ImageFile2 = Ethane-1,2-dithiol-3D-vdW.png |ImageSize2 = 150px |ImageName2 = Space-filling model of ethane-1,2-dithiol |PIN = Ethane-1,2-dithiol |OtherNames = Dimercaptoethane<br />1,2-Ethanedithiol |Section1={{Chembox Identifiers |UNII_Ref = {{fdacite|correct|FDA}} |UNII = 92T634FLAR |SMILES = SCCS |ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |ChemSpiderID = 13865015 |PubChem = 10902 |EC_number = 208-752-3 |InChI = 1/C2H6S2/c3-1-2-4/h3-4H,1-2H2 |InChIKey = VYMPLPIFKRHAAC-UHFFFAOYAA |StdInChI_Ref = {{stdinchicite|correct|chemspider}} |StdInChI = 1S/C2H6S2/c3-1-2-4/h3-4H,1-2H2 |StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |StdInChIKey = VYMPLPIFKRHAAC-UHFFFAOYSA-N |CASNo_Ref = {{cascite|correct|CAS}} |CASNo = 540-63-6 |RTECS = KI3325000 }} |Section2={{Chembox Properties | C=2 | H=6 | S=2 |Appearance = Colorless liquid |Density = 1.123 g/cm{{sup|3}} |Solubility = Slightly sol |Solvent = other solvents |SolubleOther = Good solubility in<br />most organic solvents |MeltingPtC = -41 |BoilingPtC = 146 |BoilingPt_notes = 46 mmHg |pKa = ≈11 |RefractIndex = 1.5589 (D-line, 25 °C) }} |Section7={{Chembox Hazards |NFPA-H = 2 |NFPA-F = 2 |FlashPtC = 50 |GHSPictograms = {{GHS02}}{{GHS06}}{{GHS07}} |GHSSignalWord = Danger |HPhrases = {{H-phrases|226|301|302|310|312|319|330}} |PPhrases = {{P-phrases|210|233|240|241|242|243|260|262|264|270|271|280|284|301+310|301+312|302+350|302+352|303+361+353|304+340|305+351+338|310|312|320|321|322|330|337+313|361|363|370+378|403+233|403+235|405|501}} }} |Section8={{Chembox Related |OtherFunction_label = thiols |OtherFunction = 1,1-Ethanedithiol; Ethanethiol; 1,3-Propanedithiol; 1,2-Benzenedithiol; Thiophenol }} }}
'''Ethane-1,2-dithiol''', also known as '''EDT''',<ref>{{Cite journal|last=Choi|first=H.|last2=Aldrich|first2=J.v.|date=1993-07-01|title=Comparison of methods for the Fmoc solid-phase synthesis and cleavage of a peptide containing both tryptophan and arginine|journal=International Journal of Peptide and Protein Research|language=en|volume=42|issue=1|pages=58–63|doi=10.1111/j.1399-3011.1993.tb00350.x|pmid=8103765|issn=1399-3011}}</ref> is a colorless liquid with the formula C{{sub|2}}H{{sub|4}}(SH){{sub|2}}. It has a very characteristic odor which is compared by many people to rotten cabbage. It is a common building block in organic synthesis and an excellent ligand for metal ions.
==Preparation== Ethane-1,2-dithiol is made commercially by the reaction of 1,2-dichloroethane with aqueous sodium bisulfide. In the laboratory, it can also be prepared by the action of 1,2-dibromoethane on thiourea followed by hydrolysis.<ref>{{OrgSynth | author = Speziale, A. J. | title = Ethanedithiol | collvol = 4 | collvolpages = 401 | year = 1963 | prep = cv4p0401}}</ref>
==Reactions== 1,2-Ethanedithiol is a weak acid, typical of alkyl thiols. In the presence of base and an alkylating agent, 1,2-ethanedithiol converts to thioethers: :{{chem2|HS(CH2)2SH + 2 NR3 + 2 R'I -> R'S(CH2)2SR' + 2 [R3NH]I}}
Oxidation of 1,2-ethanedithiol gives a series of oligomers, including the cyclic bis(disulfide).<ref>{{cite journal |doi=10.1016/S0040-4039(00)87577-2 |title=Preparation, Properties and Crystal Structure of 1,2,5,6-Tetrathiacyclooctane |date=1982 |last1=Goodrow |first1=Marvin H. |last2=Olmstead |first2=Marilyn M. |last3=Musker |first3=W.Kenneth |journal=Tetrahedron Letters |volume=23 |issue=32 |pages=3231–3234 }}</ref>
As a 1,2-dithiol, this compound reacts with aldehydes and ketones to give 1,3-dithiolanes, which can be useful intermediates.<ref>R. E. Conrow "Ethanedithiol" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. {{doi|10.1002/047084289X}}</ref> center|400px|Protecting a carbonyl group by converting it to a 1,3-dithiolane, using ethane-1,2-dithiol
Other 1,2- and 1,3-dithiols give related 1,3-dithiolanes (five-membered) and 1,3-dithianes (six-membered rings). Diols such as ethylene glycol undergo analogous reactions to give 1,3-dioxolanes. One distinguishing feature of the dithiolanes and dithianes derived from aldehydes is that the methyne group can be deprotonated and the resulting carbanion alkylated.
1,2-Ethanedithiol has been used as a scavenger in peptide cleavage synthesis.{{cn|date=February 2025}}
Like 1,3-propanedithiol, 1,2-ethanedithiol readily forms metal thiolate complexes. Illustrative is the synthesis of the derivative diiron ethanedithiolate hexacarbonyl upon reaction with triiron dodecacarbonyl:<ref>{{cite journal |doi=10.1016/j.ccr.2023.215174 |title=An Unexpected leading role for [Fe<sub>2</sub>(CO)<sub>6</sub>(μ-PDT)] in our Understanding of [FeFe]-H<sub>2</sub>ases and the Search for Clean Hydrogen Production |date=2023 |last1=Hogarth |first1=Graeme |journal=Coordination Chemistry Reviews |volume=490 |doi-access=free }}</ref> :Fe<sub>3</sub>(CO)<sub>12</sub> + C<sub>2</sub>H<sub>4</sub>(SH)<sub>2</sub> → Fe<sub>2</sub>(S<sub>2</sub>C<sub>2</sub>H<sub>4</sub>)(CO)<sub>6</sub> + H<sub>2</sub> + Fe(CO)<sub>5</sub> + CO
== See also == *Ethane-1,1-dithiol
==References== <references />
{{DEFAULTSORT:Ethanedithiol, 1, 2-}} Category:Alkanethiols Category:Reagents for organic chemistry Category:Chelating agents Category:Foul-smelling chemicals Category:1,2-Ethanediyl compounds