2-Mercaptopyridine

changed changed 477213812 Thiol-Thione.png skin-invert-image 240 2-Mercaptopyridine-(thiol)-3D-balls.png 2-Mercaptopyridine molecule (thiol form) 2-Mercaptopyridine-(thione)-3D-balls.png 2-Mercaptopyridine molecule (thione form) 2-Mercaptopyridine Pyridine-2-thiol 2-Thiopyridine2-ThiopyridonePyrid-2-thione2-Pyridyl mercaptan2-Pyridinethiol2-Pyridinethione correct chemspider 2005897 changed EBI 1235541 1/C5H5NS/c7-5-3-1-2-4-6-5/h1-4H,(H,6,7) correct EBI 45223 correct drugbank DB03329 220-131-9 2723698 105787 S=C1/C=C\C=C/N1 WHMDPDGBKYUEMW-UHFFFAOYAE correct chemspider 1S/C5H5NS/c7-5-3-1-2-4-6-5/h1-4H,(H,6,7) correct chemspider WHMDPDGBKYUEMW-UHFFFAOYSA-N correct CAS 73018-10-7 correct FDA EE982KT952 5 5 1 1 yellow crystalline powder 50 g/L 128 to 130 MSDS 07 Warning 315 319 335 261 264 271 280 302+352 304+340 305+351+338 312 321 332+313 337+313 362 403+233 405 501 2-Mercaptopyridine is an organosulfur compound with the formula HSC5H4N. This yellow crystalline solid is a derivative of pyridine. The compound and its derivatives serve primarily as acylating agents. A few of 2-mercaptopyridine's other uses include serving as a protecting group for amines and imides as well as forming a selective reducing agent. 2-Mercaptopyridine oxidizes to [[2,2′-dipyridyl disulfide]]. 10.1002/047084289X.rp286.pub3 2-Pyridinethiol 2007 Adams Edward J. Encyclopedia of Reagents for Organic Synthesis Skrydstrup Troels Lindsay Karl B. Skrydstrup Troels Lindsay Karl B. 978-0471936237 Preparation 2-Mercaptopyridine was originally synthesized in 1931 by heating 2-chloropyridine with calcium hydrogen sulfide. 10.1002/jlac.19314870107 Mercaptane und Sulfosäuren des Pyridins. XII. Mitteilung über Derivate des Pyridins 1931 Räth C. Binz A. Räth C. Justus Liebig's Annalen der Chemie 487 105–119 ClC5H4N + Ca(SH)2 → HSC5H4N + Ca(SH)Cl A more convenient route to 2-mercaptopyridine is the reaction of 2-chloropyridine and thiourea in ethanol and aqueous ammonia. 10.1039/JR9580003610 721. Tautomeric pyridines. Part I. Pyrid-2- and -4-thione 1958 Jones R. A. Katritzky A. R. Journal of the Chemical Society (Resumed) 3610 2-Mercaptopyridine derivatives can also be generated from precursors lacking preformed pyridine rings. It arises for example in the condensation of α,β-unsaturated ketones, malononitrile, and 4-methylbenzenethiol under microwave irradiation. The reaction is conducted with a base catalyst. 10.1002/jhet.161 An efficient and direct synthesis of 2-thiopyridinesviamicrowave-assisted three-component reaction 2009 Wang Xing-Han Cao Xu-Dong Tu Shu-Jiang Zhang Xiao-Hong Hao Wen-Juan Yan Shu Wu Shan-Shan Han Zheng-Guo Shi Feng Journal of Heterocyclic Chemistry 46 886 5 Structure and properties Similar in nature to 2-hydroxypyridine, 2-mercaptopyridine converts to the thione (or more accurately thioamide) tautomer. The preferred form is dependent on temperature, concentration, and solvent. The thiol is favored at lower temperatures, lower concentrations, and in less polar solvents. 10.1021/jo0263768 2-Pyridinethiol/2-Pyridinethione Tautomeric Equilibrium. A Comparative Experimental and Computational Study 12467429 2002 Moran Damian Sukcharoenphon Kengkaj Puchta Ralph Schaefer Henry F. Schleyer Paul v. R. Hoff Carl D. The Journal of Organic Chemistry 67 25 9061–9 10.1021/jo01296a002 Displacement of protomeric equilibriums by self-association: hydroxypyridine-pyridone and mercaptopyridine-thiopyridone isomer pairs 1980 Beak Peter Covington Johnny B. Smith Stanley G. White J. Matthew Zeigler John M. The Journal of Organic Chemistry 45 1354 8 2-Mercaptopyridine is favored in dilute solutions and in solvents capable of hydrogen bonding. These solvents will compete with other 2-mercaptopyridines to prevent self association. Thioamide-thiol tautomerism has also been demonstrated for 4-mercaptopyridine and 2-mercaptoquinoline.Kuś Piotr Jones Peter G. Quinoline-2(1 H )-thione, a structure with Z ′ = 8 Acta Crystallographica Section C Crystal Structure Communications 2004 60 12 o865–o867 10.1107/S0108270104025636 2004AcCrC..60O.865K The association constant for this reaction between mutual 2-mercaptopyridines is described below. The ratio is of monosulfide to disulfide in chloroform. Kassociation = (2.7±0.5)×103 Reactions 2-Mercaptopyridine oxidizes to 2,2'-dipyridyl disulfide. As amines are good catalysts for the oxidation of thiols to disulfides, this process is autocatalytic. 600px|class=skin-invert-image 2-Mercaptopyridine can also be prepared by hydride reduction of 2,2'-dipyridyl disulfide. C5H4NSSC5H4N + 2H → 2HSC5H4N Main reactions 2-Mercaptopyridine and the disulfide are precursors to the chelating ligand C5H4NS-. This anion forms the indium(III) complex In(PyS)3 complex. 10.1016/j.jhazmat.2007.10.052 18054158 Effect of various chelating agents on supercritical carbon dioxide extraction of indium(III) ions from acidic aqueous solution 2008 Chou Wei-Lung Yang Kai-Chiang Journal of Hazardous Materials 154 1–3 498–505 2-Mercaptopyridine has also been investigated as a reagent to purify plasmid DNA of impurities such as RNA and proteins at relatively quick timescales to similar methods.10.1002/app.24417 Biporous polymeric microspheres coupled with mercaptopyridine for rapid chromatographic purification of plasmid DNA 2007 Li Yuan Dong Xiao-Yan Sun Yan Journal of Applied Polymer Science 104 2205 4 2-Mercaptopyridine is also used acylate phenols, amines, and carboxylic acids. 2-Mercaptopyridine can be used as a catalyst for isodesmic C-H borylation of heteroarenes. The particular pattern of Lewis base and Brønsted acid allows to cleave boron-carbons bonds and then form a new boron-carbon bond by lewis pair mediated C-H activation.Rochette Étienne Desrosiers Vincent Soltani Yashar Fontaine Frédéric-Georges 2019-08-07 Isodesmic C–H Borylation: Perspectives and Proof of Concept of Transfer Borylation Catalysis https://pubs.acs.org/doi/10.1021/jacs.9b04305 Journal of the American Chemical Society en 141 31 12305–12311 10.1021/jacs.9b04305 0002-7863 31283206 195844973 References 30em Category:2-Pyridyl compounds Category:Thiols Category:Thioamides