Chemistry:1-Naphthalenethiol
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| Preferred IUPAC name
Naphthalene-1-thiol | |
| Other names
1-Mercaptonaphthalene, 1-Naphthyl mercaptan
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3D model (JSmol)
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| 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 | |
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| 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 | |
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
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
Treating 1-naphthalenethiol with butyl lithium in the presence of tmeda affords the 2-lithio derivative.[1]
References
- ↑ 1.0 1.1 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.
- ↑ 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.
- ↑ 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.
- ↑ 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.
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