1-Naphthalenethiol
{{Chembox
| ImageFile = 1-naphthalenethiol.png
| ImageSize = 134
| ImageAlt =
| PIN = Naphthalene-1-thiol
| OtherNames = 1-Mercaptonaphthalene, 1-Naphthyl mercaptan
|Section1={{Chembox Identifiers
| CASNo = 529-36-2
| PubChem = 68259
| UNII = 9A78CP495H
| ChemSpiderID = 61557
| EC_number = 208-462-7
| StdInChI=1S/C10H8S/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7,11H
| StdInChIKey = SEXOVMIIVBKGGM-UHFFFAOYSA-N
| SMILES = C1=CC=C2C(=C1)C=CC=C2S
}}
|Section2={{Chembox Properties
| C=10|H=8|S=1
| MolarMass =
| Appearance = colorless oil
| Density = 1.158 g/mL
| MeltingPtC = 15
| BoilingPtC = 285
| BoilingPt_notes =
| Solubility = }}
|Section3={{Chembox Hazards
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|302}}
| PPhrases = {{P-phrases|264|270|301+312|330|501}}
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}
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.{{cite journal |doi=10.1139/v98-230|title=A versatile synthetic route to 1,5-dithiocins from o-mercapto aromatic aldehydes|year=1999|last1=Still|first1=Ian WJ|last2=Natividad-Preyra|first2=Rosanne|last3=Toste|first3=F Dean|journal=Canadian Journal of Chemistry|volume=77|pages=113–121}}
1-Naphthalenethiol can also be prepared from 1-bromonaphthalene by Pd-catalyzed reaction with the silylthiolate iPr3SiSK followed by hydrolysis of the silathioether.{{cite journal|title=Potassium Triisopropylsilanethiolate: Vinyl and Aryl Sulfides Through Pd-Catalyzed Cross Coupling|last1=Rane|first1=Anil M.|last2=Miranda|first2=Edgar I.|last3=Soderquist|first3=John A.|journal=Tetrahed. Lett. |year=1994|volume=35|issue=20|page=3225–6|doi=10.1016/S0040-4039(00)76870-5}} 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.{{cite journal|title= Contribution to the Study of Sulphur and Selenium Compounds of the Aromatic Series|author=Taboury, F.|journal=Annales de Chimie et de Physique|year=1908|volume=15|pages=5–66}} It has been produced by the iodine-catalyzed reduction of 1-naphthalenesulfonic acid with triphenylphosphine.{{cite journal|title= Reduction of Sulfonic Acids and Related Organosulfur Compounds with the Triphenylphosphine-Iodine System|author1=Oae Shigeru|author2=Togo Hideo|journal=Bulletin of the Chemical Society of Japan|year=1983|volume=56|issue=12|pages=3801–3812|doi=10.1246/bcsj.56.3802|doi-access=}}
Reactions
Treating 1-naphthalenethiol with butyl lithium in the presence of tmeda affords the 2-lithio derivative.
References
{{Reflist}}
{{DEFAULTSORT:Naphthalenethiol, 1-}}