1-Naphthalenethiol

1-Naphthalenethiol
Names
	Preferred IUPAC name Naphthalene-1-thiol
	Other names 1-Mercaptonaphthalene, 1-Naphthyl mercaptan
Identifiers
CAS Number	529-36-2;
3D model (JSmol)	Interactive image;
ChemSpider	61557;
ECHA InfoCard	100.007.694
EC Number	208-462-7;
PubChem CID	68259;
UNII	9A78CP495H;
CompTox Dashboard (EPA)	DTXSID6060185 ;
	InChI InChI=1S/C10H8S/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7,11H Key: SEXOVMIIVBKGGM-UHFFFAOYSA-N;
	SMILES C1=CC=C2C(=C1)C=CC=C2S;
Properties
Chemical formula	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:
Pictograms
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 [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

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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[DT-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.

[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.