Nonafluoro-tert-butyl alcohol

Nonafluoro-tert-butyl alcohol
Nonafluoro-tert-butyl alcohol
Names
Preferred IUPAC name
1,1,1,3,3,3-Hexafluoro-2-(trifluoromethyl)propan-2-ol
Other names
perfluoro-tert-butyl alcohol, perfluoro-tert-butanol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.017.417 Edit this at Wikidata
EC Number
  • 219-157-3
  • InChI=1S/C4HF9O/c5-2(6,7)1(14,3(8,9)10)4(11,12)13/h14H
  • OC(C(F)(F)F)(C(F)(F)F)C(F)(F)F
Properties
C4F9OH
Molar mass 236.04 g/mol
Appearance Colorless liquid
Boiling point 45 °C (113 °F; 318 K)
Miscible
Acidity (pKa) 5.4 (in H2O)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Corrosive, eye irritant
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Nonafluoro-tert-butyl alcohol (IUPAC name: 1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-ol) is a fluoroalcohol. It is the perfluorinated analog of tert-butyl alcohol. Notably, as a consequence of its electron withdrawing fluorine substituents, it is very acidic for an alcohol, with a pKa value of 5.4, similar to that of a carboxylic acid. As another consequence of being a perfluorinated compound, it is also one of the lowest boiling alcohols, with a boiling point lower than that of methanol.

Synthesis

It is prepared by addition of trichloromethyllithium to hexafluoroacetone, followed by halogen exchange with antimony pentafluoride.[1] The aluminate derived from its alkoxide anion, tetrakis[1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)propan-2-oxy]aluminate(1–), {Al[(CF3)3CO]4}– is used as a weakly coordinating anion.[2]

See also

References

  1. ^ Filler, Robert; Schure, Ralph M. (1967-04-01). "Highly acidic perhalogenated alcohols. A new synthesis of perfluoro-tert-butyl alcohol". The Journal of Organic Chemistry. 32 (4): 1217–1219. doi:10.1021/jo01279a081. ISSN 0022-3263.
  2. ^ Krossing, Ingo; Raabe, Ines (2004-04-13). "Noncoordinating Anions—Fact or Fiction? A Survey of Likely Candidates". Angewandte Chemie International Edition. 43 (16): 2066–2090. doi:10.1002/anie.200300620. ISSN 1433-7851. PMID 15083452.