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2-Naphthalenethiol
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2-naphthalenethiol.png Naphthalene-2-thiol 91-60-1 7058 SZ5U1S741V 6791 202-082-5 1S/C10H8S/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7,11H RFCQDOVPMUSZMN-UHFFFAOYSA-N C1=CC=C2C=C(C=CC2=C1)S 10 8 1 White solid Sulfurous, mercaptan, burnt rubber, 80–81 92–94 (at 0.4 mmHg) 07 warning 302 264 270 301+312 330 501
2-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 1-naphthalenethiol.
Synthesis and reactions
2-Naphthalenethiol is prepared from 2-naphthol by the Newman–Kwart rearrangement starting from a thiocarbamate.Thiophenols from Phenols: 2-Naphthalenethiol Melvin S. Newman Frederick W. Hetzel Org. Synth. 1971 51 139 10.15227/orgsyn.051.0139 free It undergoes lithiation at the 1 and 3-position.Block, E. Eswarakrishnan, V. Gernon, M. Ofori-Okai, G. Saha, C. Tang, K. Zubieta, J. o-Lithiothiophenol Equivalents. Generation, Reactions and Applications in Synthesis of Hindered Thiolate Ligands J. Am. Chem. Soc. 1989 111 2 658–665 10.1021/ja00184a03910.1139/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
It can be used as a flavouring agent and has been described as having an “artichoke”, “meaty” and “creamy” taste”.WHO World Health Evaluations of the Joint FAO/WHO Expert Committee on Food Additives (JECFA) Feedback Print preview Link to this page 2-NAPHTHALENETHIOL http://apps.who.int/food-additives-contaminants-jecfa-database/chemical.aspx?chemID=2896 apps.who.int 15 January 2018https://hmdb.ca/metabolites/HMDB0029689#:~:text=2%2DNaphthalenethiol%20is%20an%20artichoke,creamy%2C%20and%20meaty%20tasting%20compound Human Metabolome Database: Showing metabocard for 2-Naphthalenethiol (HMDB0029689)
References
Category:Thiols
Category:2-Naphthyl compounds