Misplaced Pages

Pentafluorothiophenol

Article snapshot taken from[REDACTED] with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
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
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.011.124 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6HF5S/c7-1-2(8)4(10)6(12)5(11)3(1)9/h12HKey: UVAMFBJPMUMURT-UHFFFAOYSA-N
  • InChI=1/C6HF5S/c7-1-2(8)4(10)6(12)5(11)3(1)9/h12HKey: UVAMFBJPMUMURT-UHFFFAOYAU
SMILES
  • c1(c(c(c(c(c1F)F)S)F)F)F
Properties
Chemical formula C6HF5S
Molar mass 200.13
Appearance colorless liquid
Density 1.625±0.06 g/cm
Melting point −24 °C (−11 °F; 249 K)
Boiling point 143 °C (289 °F; 416 K)
Solubility in water organic solvents
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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. With a pKa of 2.68, it is one of the most acidic thiols. Its conjugate base has been used as a ligand in coordination chemistry

Related compounds

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
Categories:
Pentafluorothiophenol Add topic