24197-80-6

Basic information

• Product Name: S-phenyl naphthalene-1-carbothioate
• Synonyms: S-phenyl naphthalene-1-carbothioate
• CAS NO: 24197-80-6
• Molecular Weight: 264.348
• Mol File: 24197-80-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: S-phenyl naphthalene-1-carbothioate(CAS DataBase Reference)
• NIST Chemistry Reference: S-phenyl naphthalene-1-carbothioate(24197-80-6)
• EPA Substance Registry System: S-phenyl naphthalene-1-carbothioate(24197-80-6)

Safety Data

• Hazardous Substances Data: 24197-80-6(Hazardous Substances Data)

Upstream product

• 108-98-5 thiophenol 
• 879-18-5 naphthalene-1-carbonic acid chloride 
• 201230-82-2 carbon monoxide 
• 90-14-2 1-Iodonaphthalene 
• 1012-56-2 (Et)3tin(phenylthiolate) 
• 4551-15-9 phenylthiotrimethylsilane 
• 90-11-9 1-Bromonaphthalene 
• 82102-37-2 9-methyl-9H-fluorene-9-carbonyl chloride 

Downstream Products

• 86-55-5 1-naphthalenecarboxylic acid 
• 108-98-5 thiophenol 
• 7570-98-1 1-naphthyl phenyl sulfide 

Relevant articles and documents

Palladium-catalyzed thiocarbonylation of aryl, vinyl, and benzyl bromides

(Chemical Equation Presented) A catalytic protocol for synthesis of thioesters from aryl, vinyl, and benzyl bromides as well as benzyl chlorides was developed using only stoichiometric amounts of carbon monoxide, produced from a solid CO precursor inside a two-chamber system. As a catalytic system, the combination of bis(benzonitrile) palladium(II) chloride and Xantphos furnished the highest yields of the desired compounds, along with the weak base, NaOAc, in anisole at 120°C. The choice of catalytic system as well as solvent turned out to be important in order to ensure a high chemoselectivity in the reaction. Both electron-rich and electron-deficient aryl bromides worked well in this reaction. Addition of 1 equiv of sodium iodide to the reaction improved the chemoselectivity with the electron-deficient aryl bromides. The thiol scope included both aryl and alkyl thiols, including 2-mercaptobenzophenones, whereby a thiocarbonylation followed by a subsequent McMurry coupling yielded differently substituted benzothiophenes. It was demonstrated that the methodology could be applied for 13C introduction into the thiophene ring.

REACTIONS OF ORGANOMETALLIC COMPOUNDS CATALYZED BY TRANSITION-METAL COMPLEXES. XV. PRODUCTION OF THIOCARBOXYLIC S-ESTERS BY CATALYTIC CARBONYLATION OF ARYL IODIDES AND TRIETHYLTIN THIOLATES

Carbonylation in the aryl iodide-triethyltin thiolate system, catalyzed by bis(triphenylphosphine) palladium, was studied.In the case of unactivated aryl iodides containing weak electron-withdrawing substituents thiocarboxylic S-esters are formed with satisfactory yields.The reactions of aryl iodides containing strong electron-withdrawing groups lead mainly to the products from cross-coupling, i.e., unsymmetrical sulfides.The mechanism of the catalytic action of the phosphine complex of palladium was investigated.

Thiocarbonic acid-S-esters and their polarographic behavior

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