Silver(I) trifluoromethanethiolate Chemical Properties

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

Water Solubility 

Insoluble in water

solubility 

Methanol

form 

powder to crystal

color 

White to Light yellow to Light red

InChI

InChI=1S/CHF3S.Ag/c2-1(3,4)5;/h5H;

InChIKey

SVPQZGWGYCARGG-UHFFFAOYSA-N

SMILES

C(S)(F)(F)F.[Ag]

Safety Information

HS Code 

2843290090

Silver(I) trifluoromethanethiolate Usage And Synthesis

Uses

Silver(I) trifluoromethanethiolate is an important organic synthesis intermediate and pharmaceutical intermediate for the preparation of trifluoromethyl aryl sulfides and indanone derivatives^[1-2].

Synthesis

Silver tetrafluoroborate (AgBF4, 19.77 g, 100 mmol) and sodium trifluoromethanesulfinate (CF3SO2Na, 18.73 g, 120 mmol) were dissolved in anhydrous acetonitrile (400 mL) under nitrogen protection. After cooling the reaction mixture to 0°C, triphenylphosphine (Ph3P, 62.95 g, 240 mmol) was slowly added. Subsequently, the reaction mixture was brought back to room temperature and heated to 50°C and maintained at this temperature for 12 hours. Upon completion of the reaction, the mixture was filtered through diatomaceous earth and the filtrate was cooled to -20°C to promote crystallization. After the crystals were sufficiently precipitated, the supernatant was decanted to remove most of the triphenylphosphine oxide. The supernatant was concentrated under reduced pressure to remove the solvent and the residue was washed well with ether and dried under vacuum. Finally, the resulting solid was recrystallized with tetrahydrofuran and benzene to afford silver trifluoromethane thiol (I) (18.60 g, 89% yield).

References

[1] DAVE J. ADAMS, James H C. ChemInform Abstract: Preparation of Trifluoromethyl Aryl Sulfides Using Silver(I) Trifluoromethanethiolate and an Inorganic Iodide.[J]. ChemInform, 2010, 31 23. DOI:10.1002/chin.200023091.
[2] YI-KANG SONG. Synthesis of 2-(trifluoromethylthio)-indenones by silver-mediated cascade trifluoromethylthiolation/cyclization of arylpropynones[J]. Tetrahedron, 2016, 72 47: Pages 7589-7593. DOI:10.1016/j.tet.2016.10.013.

Silver(I) trifluoromethanethiolate(811-68-7)Related Product Information

• Bismuth(III) trifluoromethanesulfonate
• Zinc trifluoromethanesulfonate
• SAMARIUM(III) TRIFLUOROMETHANESULFONATE
• YTTERBIUM(III) TRIFLUOROMETHANESULFONATE HYDRATE
• Trifluoromethanesulfonamide
• Ethyl trifluoromethanesulfonate
• Scandium trifluoromethanesulfonate
• SILVER TRIFLUOROMETHANESULFONATE
• TRIFLUOROMETHYL SULFINYL CHLORIDE
• YTTERBIUM(III) TRIFLATE HYDRATE, 99.90%
• COPPER(II) TRIFLUOROMETHANESULFONATE
• Trifluoromethanesulfonyl chloride
• Silver chloride
• Silver cyanide
• SILVER BROMIDE
• (Trifluoromethylsulfonyloxy) copper(I)
• Iron(III) trifluoromethanesulfonate
• EUROPIUM TRIFLUOROMETHANESULFONATE