Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Ethane-1,2-dithiol: Difference between pages

|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 = [[thiol]]s

|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 [[Chemical formula|formula]] [[Carbon|C]]{{sub|2}}[[Hydrogen|H]]{{sub|4}}([[Thiol|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>

==Applications==

As a 1,2-[[dithiol]], this compound is widely used in organic chemistry because it reacts with [[aldehyde]]s and [[ketone]]s to give 1,3-[[dithiolane]]s, which are 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>

::C{{sub|2}}H{{sub|4}}(SH){{sub|2}} + RR'CO → C{{sub|2}}H{{sub|4}}S{{sub|2}}CRR' + H{{sub|2}}O

[[File:Carbonyl-protection-with-ethanedithiol-2D.png|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 undergo this reaction to give related 1,3-dithiolanes and 1,3-dithianes (six-membered rings). [[Diol]]s such as [[ethylene glycol]] undergo analogous reactions to 1,3-[[dioxolane]]s and 1,3-[[dioxane]]s. 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 is commonly used as a scavenger in peptide cleavage synthesis.

== See also ==

*[[Ethane-1,1-dithiol]]

==References==

<references />

{{DEFAULTSORT:Ethanedithiol, 1, 2-}}

[[Category:Thiols]]

[[Category:Reagents for organic chemistry]]

[[Category:Chelating agents]]

[[Category:Foul-smelling chemicals]]

[[Category:1,2-Ethanediyl compounds]]