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
CAS Number	771-62-0  Y
3D model (JSmol)	Interactive image
ChemSpider	12500
ECHA InfoCard	100.011.124
PubChem CID	13042
UNII	CM7UNQ95TJ  Y
CompTox Dashboard (EPA)	DTXSID10227887
InChI 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
SMILES c1(c(c(c(c(c1F)F)S)F)F)F
Properties
Chemical formula	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)
Solubility in water	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 C ₆ F ₅ S H . It is a colorless volatile liquid. The compound is prepared by the reaction of sodium hydrosulfide and hexafluorobenzene. ^[1] With a pK_a 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]

Related compounds

• Pentafluorophenol

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