Pentafluorothiophenol

Pentafluorothiophenol
Names
Preferred IUPAC name
Pentafluorobenzenethiol
Other names
  • Pentafluorophenylthiol
  • 2,3,4,5,6-Pentafluorobenzenethiol
  • 2,3,4,5,6-Pentafluorothiophenol
  • Mercapto(pentafluoro)benzene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.011.124
UNII
  • InChI=1S/C6HF5S/c7-1-2(8)4(10)6(12)5(11)3(1)9/h12H
    Key: UVAMFBJPMUMURT-UHFFFAOYSA-N
  • InChI=1/C6HF5S/c7-1-2(8)4(10)6(12)5(11)3(1)9/h12H
    Key: UVAMFBJPMUMURT-UHFFFAOYAU
  • c1(c(c(c(c(c1F)F)S)F)F)F
Properties
C6F5SH
Molar mass 200.13 g·mol−1
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
Acidity (pKa) 2.68
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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]

References

  1. ^ 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
  2. ^ 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
  3. ^ 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
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