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.
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Preferred IUPAC name
1,1,1,3,3,3-Hexafluoro-2-(trifluoromethyl)propan-2-ol | |
Other names
perfluoro-tert-butyl alcohol, perfluoro-tert-butanol
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Identifiers | |
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3D model (JSmol)
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ChemSpider |
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ECHA InfoCard | 100.017.417 |
EC Number |
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PubChem CID
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CompTox Dashboard (EPA)
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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
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Corrosive, eye irritant |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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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]