1-Naphthalenethiol

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1-Naphthalenethiol
1-naphthalenethiol.png
Names
Preferred IUPAC name
Naphthalene-1-thiol
Other names
1-Mercaptonaphthalene, 1-Naphthyl mercaptan
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.694 Edit this at Wikidata
EC Number
  • 208-462-7
UNII
  • InChI=1S/C10H8S/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7,11H
    Key: SEXOVMIIVBKGGM-UHFFFAOYSA-N
  • C1=CC=C2C(=C1)C=CC=C2S
Properties
C10H8S
Molar mass 160.23 g·mol−1
Appearance colorless oil
Density 1.158 g/mL
Melting point 15 °C (59 °F; 288 K)
Boiling point 285 °C (545 °F; 558 K)
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).

1-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 2-naphthalenethiol.

Synthesis[edit]

A practical synthesis involves the tin/HCl-reduction of the naphthalene-1-sulfonyl chloride.[1] 1-Naphthalenethiol can also be prepared from 1-bromonaphthalene by Pd-catalyzed reaction with the silylthiolate iPr3SiSK followed by hydrolysis of the silathioether.[2] It was first prepared from the Grignard reagent generated from 1-bromonaphthalene. Treatment of that reagent with elemental sulfur followed by acidification gave the compound.[3] It has been produced by the iodine-catalyzed reduction of 1-naphthalenesulfonic acid with triphenylphosphine.[4]

Reactions[edit]

Treating 1-naphthalenethiol with butyl lithium in the presence of tmeda affords the 2-lithio derivative.[1]

References[edit]

  1. ^ a b 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.
  2. ^ Rane, Anil M.; Miranda, Edgar I.; Soderquist, John A. (1994). "Potassium Triisopropylsilanethiolate: Vinyl and Aryl Sulfides Through Pd-Catalyzed Cross Coupling". Tetrahed. Lett. 35 (20): 3225–6. doi:10.1016/S0040-4039(00)76870-5.
  3. ^ Taboury, F. (1908). "Contribution to the Study of Sulphur and Selenium Compounds of the Aromatic Series". Annales de Chimie et de Physique. 15: 5–66.
  4. ^ Oae Shigeru; Togo Hideo (1983). "Reduction of Sulfonic Acids and Related Organosulfur Compounds with the Triphenylphosphine-Iodine System". Bulletin of the Chemical Society of Japan. 56 (12): 3801–3812. doi:10.1246/bcsj.56.3802.