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	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
	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). verify (what is ?) Infobox references

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.

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]

References

^ 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.
^ 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.

[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.

[1]

[2]

Synthesis

See also

References