2-Naphthalenethiol

From Wikipedia, the free encyclopedia
2-Naphthalenethiol
2-naphthalenethiol.png
Names
Preferred IUPAC name
Naphthalene-2-thiol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.893 Edit this at Wikidata
EC Number
  • 202-082-5
UNII
  • InChI=1S/C10H8S/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7,11H
    Key: RFCQDOVPMUSZMN-UHFFFAOYSA-N
  • C1=CC=C2C=C(C=CC2=C1)S
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 labelling:
GHS07: Exclamation mark
Warning
H302
P264, P270, P301+P312, P330, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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[edit]

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.[4]

References[edit]

  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.