1,3-Propanedithiol

Chemical compound changed changed 477205579 1,3-Propanedithiol 1,3-Propandithiol Structural Formula V1.svg 200px 1,3-Propanedithiol 1,3-Propanedithiol-3D-balls.png 1,3-Propanedithiol molecule Propane-1,3-dithiol 1,3-Dimercaptopropane SCCCS correct chemspider correct EBI 44864 13848090 changed EBI 1235209 8013 203-706-9 3336 R4LUJ82U52 1/C3H8S2/c4-2-1-3-5/h4-5H,1-3H2 ZJLMKPKYJBQJNH-UHFFFAOYAS correct chemspider 1S/C3H8S2/c4-2-1-3-5/h4-5H,1-3H2 correct chemspider ZJLMKPKYJBQJNH-UHFFFAOYSA-N correct CAS 109-80-8 TZ2585500 3 8 2 Colorless liquid Offensive 1.078 g/cm3 slight solvents all organic solvents -79 169 1.539 0 D stench 138 07 Warning 302 315 319 335 261 264 270 271 280 301+312 302+352 304+340 305+351+338 312 321 330 332+313 337+313 362 403+233 405 501 1,2-ethanedithiol1,2-propanedithiollipoic acid 1,3-Propanedithiol is the chemical compound with the formula HSCH2CH2CH2SH. This dithiol is a useful reagent in organic synthesis. This liquid, which is readily available commercially, has an intense stench. Reactions 1,3-Propanedithiol has been used for the protection of aldehydes and ketones via their reversible formation of dithianes.Conrow, R. E. Le Huérou, Y. 1,3-Propanedithiol Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004 J. Wiley & Sons, New York 10.1002/047084289X 10261/236866 9780471936237 free A prototypical reaction is its formation of 1,3-dithiane from formaldehyde. Corey, E. J. Seebach, D. 1,3-Dithiane 1988 6 556 cv6p0556 The reactivity of this dithiane illustrates the concept of umpolung. Alkylation gives thioethers, e.g. 1,5-dithiacyclooctane. The unpleasant odour of 1,3-propanedithiol has encouraged the development of alternative reagents that generate similar derivatives.Liu, Q. Che, G. Yu, H. Liu, Y. Zhang, J. Zhang, Q. Dong, D. The First Nonthiolic, Odorless 1,3-Propanedithiol Equivalent and Its Application in Thioacetalization Journal of Organic Chemistry 2003 68 9148–9150 10.1021/jo034702t 14604400 23 Oxidation gives not the 1,2-dithiolane, but the bis(disulfide). thumb|left|120px|Structure of (C3H6S2)2, the oxidized "dimer" of 1,3-propanedithiol.10.1080/03086648308080483 Preparation and X-Ray Crystal Structure of the Cyclic Dimer of 1,2-Dithiolane: 1,2,6,7-Tetrathiacyclodecane 1983 Goodrow Marvin H. Olmstead Marilyn M. Musker W. Kenneth Phosphorus and Sulfur and the Related Elements 16 3 299–302 1,3-Propanedithiol is used in the synthesis of tiapamil. 1,3-Propanedithiol reacts with metal ions to form dithiolates. Illustrative is the synthesis of the derivative diiron propanedithiolate 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 Fe3(CO)12 + C3H6(SH)2 → Fe2(S2C3H6)(CO)6 + H2 + Fe(CO)5 + CO Safety The stench of 1,3-propanedithiol can be minimized with bleach. See also 1,2-Propanedithiol References Category:Reagents for organic chemistry Category:Alkanethiols Category:Foul-smelling chemicals Category:1,3-Propanediyl compounds