Pentafluorothiophenol is an organosulfur compound with the formula C6F5SH. It is a colorless volatile liquid. The compound is prepared by the reaction of sodium hydrosulfide and hexafluorobenzene.[1] With a pKa of 2.68, it is one of the most acidic thiols.[2] Its conjugate base has been used as a ligand in coordination chemistry[3]
Names | |
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Preferred IUPAC name
Pentafluorobenzenethiol | |
Other names
Pentafluorophenylthiol, 2,3,4,5,6-pentafluorobenzenethiol, 2,3,4,5,6-pentafluorothiophenol. mercapto(pentafluoro)benzene
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Identifiers | |
3D model (JSmol)
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ChemSpider | |
ECHA InfoCard | 100.011.124 |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C6HF5S | |
Molar mass | 200.13 |
Appearance | colorless liquid |
Density | 1.625±0.06 g/cm3 |
Melting point | −24 °C (−11 °F; 249 K) |
Boiling point | 143 °C (289 °F; 416 K) |
organic solvents | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Related compounds
editReferences
edit- ^ Robson, P.; Stacey, M.; Stephens, R.; Tatlow, J. C. "Aromatic polyfluoro compounds. VI. Penta- and 2,3,5,6-tetrafluorothiophenol" Journal of the Chemical Society (1960), 4754-60. doi:10.1039/jr9600004754
- ^ William P. Jencks, Karin Salvesen "Equilibrium deuterium isotope effects on the ionization of thiol acids" J. Am. Chem. Soc., 1971, volume 93, pp 4433–4436. doi:10.1021/ja00747a016
- ^ Torrens, Hugo "Pentafluorobenzenethiolato derivatives of the platinum group metals" Coordination Chemistry Reviews, 2000, vol. 196, pp. 331-352. doi:10.1016/S0010-8545(99)00055-7