Nonafluoro-tert-butyl alcohol

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 pK_a 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. 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]

Nonafluoro-tert-butyl alcohol

Names
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	2378-02-1
3D model (JSmol)	Interactive image
ChemSpider	16035
ECHA InfoCard	100.017.417
EC Number	219-157-3
PubChem CID	16924
CompTox Dashboard (EPA)	DTXSID5073292
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
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).
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Infobox references

See also

• 2,2,2-Trifluoroethanol
• 1,1,1,3,3,3-Hexafluoro-2-propanol
• Hexafluoroacetone

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.