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2-Naphthalenethiol

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.[1] It undergoes lithiation at the 1 and 3-position.[2][3]

It can be used as a flavouring agent and has been described as having an “artichoke”, “meaty” and “creamy” taste”.[4][5]

References

  1. ^ Melvin S. Newman; Frederick W. Hetzel (1971). "Thiophenols from Phenols: 2-Naphthalenethiol". Org. Synth. 51: 139. doi:10.15227/orgsyn.051.0139.
  2. ^ Block, E.; Eswarakrishnan, V.; Gernon, M.; Ofori-Okai, G.; Saha, C.; Tang, K.; Zubieta, J. (1989). "o-Lithiothiophenol Equivalents. Generation, Reactions and Applications in Synthesis of Hindered Thiolate Ligands". J. Am. Chem. Soc. 111 (2): 658–665. doi:10.1021/ja00184a039.
  3. ^ Still, Ian WJ; Natividad-Preyra, Rosanne; Toste, F Dean (1999). "A versatile synthetic route to 1,5-dithiocins from o-mercapto aromatic aldehydes". Canadian Journal of Chemistry. 77: 113–121. doi:10.1139/v98-230.
  4. ^ WHO, World Health. "Evaluations of the Joint FAO/WHO Expert Committee on Food Additives (JECFA) Feedback Print preview Link to this page 2-NAPHTHALENETHIOL". apps.who.int. Retrieved 15 January 2018.
  5. ^ "Human Metabolome Database: Showing metabocard for 2-Naphthalenethiol (HMDB0029689)".