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Nonafluoro-tert-butyl alcohol

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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
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.017.417 Edit this at Wikidata
EC Number
  • 219-157-3
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C4HF9O/c5-2(6,7)1(14,3(8,9)10)4(11,12)13/h14H
SMILES
  • OC(C(F)(F)F)(C(F)(F)F)C(F)(F)F
Properties
Chemical formula C4F9OH
Molar mass 236.04 g/mol
Appearance Colorless liquid
Boiling point 45 °C (113 °F; 318 K)
Solubility in water 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 , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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. The aluminate derived from its alkoxide anion, tetrakisaluminate(1–), {Al4} is used as a weakly coordinating anion.

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.
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