1-Naphthalenethiol

1-naphthalenethiol.png 134 Naphthalene-1-thiol 1-Mercaptonaphthalene, 1-Naphthyl mercaptan 529-36-2 68259 9A78CP495H 61557 208-462-7 1S/C10H8S/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7,11H SEXOVMIIVBKGGM-UHFFFAOYSA-N C1=CC=C2C(=C1)C=CC=C2S 10 8 1 colorless oil 1.158 g/mL 15 285 07 Warning 302 264 270 301+312 330 501 1-Naphthalenethiol is an organosulfur compound with the formula C10H7SH. It is a white solid. It is one of two monothiols of naphthalene, the other being 2-naphthalenethiol. Synthesis A practical synthesis involves the tin/HCl-reduction of the naphthalene-1-sulfonyl chloride.10.1139/v98-230 A versatile synthetic route to 1,5-dithiocins from o-mercapto aromatic aldehydes 1999 Still Ian WJ Natividad-Preyra Rosanne Toste F Dean Canadian Journal of Chemistry 77 113–121 1-Naphthalenethiol can also be prepared from 1-bromonaphthalene by Pd-catalyzed reaction with the silylthiolate iPr3SiSK followed by hydrolysis of the silathioether.Potassium Triisopropylsilanethiolate: Vinyl and Aryl Sulfides Through Pd-Catalyzed Cross Coupling Rane Anil M. Miranda Edgar I. Soderquist John A. Tetrahed. Lett. 1994 35 20 3225–6 10.1016/S0040-4039(00)76870-5 It was first prepared from the Grignard reagent generated from 1-bromonaphthalene. Treatment of that reagent with elemental sulfur followed by acidification gave the compound. Contribution to the Study of Sulphur and Selenium Compounds of the Aromatic Series Taboury, F. Annales de Chimie et de Physique 1908 15 5–66 It has been produced by the iodine-catalyzed reduction of 1-naphthalenesulfonic acid with triphenylphosphine. Reduction of Sulfonic Acids and Related Organosulfur Compounds with the Triphenylphosphine-Iodine System Oae Shigeru Togo Hideo Bulletin of the Chemical Society of Japan 1983 56 12 3801–3812 10.1246/bcsj.56.3802 Reactions Treating 1-naphthalenethiol with butyl lithium in the presence of tmeda affords the 2-lithio derivative. References Category:Thiols Category:1-Naphthyl compounds Category:Foul-smelling chemicals