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2-Naphthalenethiol

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2-Naphthalenethiol
Names
Preferred IUPAC name Naphthalene-2-thiol
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.893 Edit this at Wikidata
EC Number
  • 202-082-5
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H8S/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7,11HKey: RFCQDOVPMUSZMN-UHFFFAOYSA-N
SMILES
  • C1=CC=C2C=C(C=CC2=C1)S
Properties
Chemical formula C10H8S
Molar mass 160.23 g·mol
Appearance White solid
Odor Sulfurous, mercaptan, burnt rubber,
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 labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H302
Precautionary statements P264, P270, P301+P312, P330, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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. It undergoes lithiation at the 1 and 3-position.

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

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)".
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