Chemistry:2-Naphthalenethiol
From HandWiki
| |
| Names | |
|---|---|
| Preferred IUPAC name
Naphthalene-2-thiol | |
| Identifiers | |
3D model (JSmol)
|
|
| ChemSpider | |
| EC Number |
|
PubChem CID
|
|
| UNII | |
| |
| |
| Properties | |
| C10H8S | |
| Molar mass | 160.23 g·mol−1 |
| Appearance | White solid |
| Melting point | 80–81 °C (176–178 °F; 353–354 K) |
| Boiling point | 92–94 °C (198–201 °F; 365–367 K) (at 0.4 mmHg) |
| Hazards | |
| GHS pictograms | 
|
| GHS Signal word | warning |
| H302 | |
| P264, P270, P301+312, P330, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
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
- ↑ Melvin S. Newman; Frederick W. Hetzel (1971). "Thiophenols from Phenols: 2-Naphthalenethiol". Org. Synth. 51: 139. doi:10.15227/orgsyn.051.0139.
- ↑ 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.
- ↑ 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.
- ↑ 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. Retrieved 15 January 2018.
- ↑ "Human Metabolome Database: Showing metabocard for 2-Naphthalenethiol (HMDB0029689)". https://hmdb.ca/metabolites/HMDB0029689#:~:text=2%2DNaphthalenethiol%20is%20an%20artichoke,creamy%2C%20and%20meaty%20tasting%20compound.
 |  |
