1,2-Ethanedithiol

Chemical compound C2H4(SH)2 changed 477204496 Ethane-1,2-dithiol Ethanedithiol.png 150px Ethane-1,2-dithiol Ethane-1,2-dithiol-3D-balls.png 150px Ball-and-stick model of ethane-1,2-dithiol Ethane-1,2-dithiol-3D-vdW.png 150px Space-filling model of ethane-1,2-dithiol Ethane-1,2-dithiol Dimercaptoethane1,2-Ethanedithiol correct FDA 92T634FLAR SCCS correct chemspider 13865015 10902 208-752-3 1/C2H6S2/c3-1-2-4/h3-4H,1-2H2 VYMPLPIFKRHAAC-UHFFFAOYAA correct chemspider 1S/C2H6S2/c3-1-2-4/h3-4H,1-2H2 correct chemspider VYMPLPIFKRHAAC-UHFFFAOYSA-N correct CAS 540-63-6 KI3325000 2 6 2 Colorless liquid 1.123 g/cm3 Slightly sol other solvents Good solubility inmost organic solvents -41 146 46 mmHg ≈11 1.5589 (D-line, 25 °C) 2 2 50 02 06 07 Danger 226 301 302 310 312 319 330 210 233 240 241 242 243 260 262 264 270 271 280 284 301+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 thiols 1,1-Ethanedithiol; Ethanethiol; 1,3-Propanedithiol; 1,2-Benzenedithiol; Thiophenol Ethane-1,2-dithiol, also known as EDT,Choi H. Aldrich J.v. 1993-07-01 Comparison of methods for the Fmoc solid-phase synthesis and cleavage of a peptide containing both tryptophan and arginine International Journal of Peptide and Protein Research en 42 1 58–63 10.1111/j.1399-3011.1993.tb00350.x 8103765 1399-3011 is a colorless liquid with the formula C2H4(SH)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. Speziale, A. J. Ethanedithiol 4 401 1963 cv4p0401 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: 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).10.1016/S0040-4039(00)87577-2 Preparation, Properties and Crystal Structure of 1,2,5,6-Tetrathiacyclooctane 1982 Goodrow Marvin H. Olmstead Marilyn M. Musker W.Kenneth Tetrahedron Letters 23 32 3231–3234 As a 1,2-dithiol, this compound reacts with aldehydes and ketones to give 1,3-dithiolanes, which can be useful intermediates.R. E. Conrow "Ethanedithiol" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. 10.1002/047084289X 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.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:10.1016/j.ccr.2023.215174 An Unexpected leading role for [Fe2(CO)6(μ-PDT)] in our Understanding of [FeFe]-H2ases and the Search for Clean Hydrogen Production 2023 Hogarth Graeme Coordination Chemistry Reviews 490 free https://kclpure.kcl.ac.uk/portal/en/publications/6b54bfc3-17e6-4382-a8f1-7cc22b0375c8 Fe3(CO)12 + C2H4(SH)2 → Fe2(S2C2H4)(CO)6 + H2 + Fe(CO)5 + CO See also Ethane-1,1-dithiol References Category:Alkanethiols Category:Reagents for organic chemistry Category:Chelating agents Category:Foul-smelling chemicals Category:1,2-Ethanediyl compounds Category:Organic compounds with 2 carbon atoms