Hexafluoro-2-propanol

Chembox new
Name = 1,1,1,3,3,3-Hexafluoro-2-propanol
ImageFile = Hexafluoroisopropanol.svg
ImageFile2 = Hexafluoroisopropanol 3D.png ImageName = 1,1,1,3,3,3-Hexafluoro-2-propanol
IUPACName = 1,1,1,3,3,3-Hexafluoro
-2-propanol
OtherNames = Hexafluoroisopropanol,
Hexafluoroisopropyl alcohol,
HFIP
Section1 = Chembox Identifiers
SMILES = C(F)(F)(F)C(O)C(F)(F)(F)
CASNo = 920-66-1
RTECS = UB6450000
Section2 = Chembox Properties
Formula = C₃H₂F₆O
MolarMass = 168.05 g/mol
Appearance = Colorless liquid
Density = 1.596 g/ml, liquid
Solubility = Miscible, 100 g/100 ml (25°C)
Solvent = other solvents
SolubleOther = Miscible
MeltingPt = −3.3°C (269 K)
BoilingPt = 58.2°C (331 K)
Viscosity = 1.65 cP at 20°C
Section7 = Chembox Hazards
ExternalMSDS = [http://ptcl.chem.ox.ac.uk/MSDS/HE/1,1,1,3,3,3-hexafluoro-2-propanol.html External MSDS]
MainHazards = Corrosive (C)
NFPA-H = 3
NFPA-R = 0
NFPA-F = 0
FlashPt = >373°C
RPhrases = R20/22, R34, R41
SPhrases = S26, S36/37/39, S45
Section8 = Chembox Related
Function = alcohols
OtherFunctn = Isopropyl alcohol
2,2,2-Trifluoroethanol
Function = s
OtherFunctn = Hexafluoro-2-propanone

Hexafluoroisopropanol, commonly abbreviated HFIP is the organic compound with the formula (CF₃)₂CHOH. This
fluorinated alcohol finds use as solvent for polymer systems. It appears as a colorless, volatile liquid that is characterized by a strong, pungent odor. As a solvent hexafluoro-2-propanol exhibits strong hydrogen bonding properties enabling it to dissolve substances that serve as hydrogen-bond acceptors, such as amides and ethers. Hexafluoro-2-propanol is also a polar compound, transparent to UV light with high density, low viscosity and low refractive index.

Production

Hexafluoro-2-propanol is prepared from hexafluoropropylene via hexafluoroacetone, which is reduced by catalytic hydrogenation or by hydride reagents.Günter Siegemund, Werner Schwertfeger, Andrew Feiring, Bruce Smart, Fred Behr, Herward Vogel, Blaine McKusick “Fluorine Compounds, Organic” Ullmann's Encyclopedia of Industrial Chemistry, John Wiley & Sons, 2007.] :(CF₃)₂CO + H₂ → (CF₃)₂CHOH

Uses

Hexafluoro-2-propanol is a specialty solvent in organic synthesis [ "Review": Bégué, J.-P.; Bonnet-Delpon, D.; Crousse, B. Fluorinated Alcohols: A New Medium for Selective and Clean Reaction. "Synthesis", 2004,(1), pp. 18-29.] [ "Review": Shuklov, Ivan A. ; Dubrovina, Natalia V.; Börner, Armin doi-inline|10.1055/s-2007-983902|Fluorinated Alcohols as Solvents, Cosolvents and Additives in Homogeneous Catalysis, "Synthesis" 2007, pp. 2925-2943] due to its properties which make it especially useful to solubilize a wide range of polymers, including those that are not soluble in the most common organic solvents: such as polyamides, polyacrylonitriles, polyacetals, polyesters (e.g. polyglycolide), and polyketones. Because of its acidity (pK_a = 9.3), it can be used as acid in volatile buffers for ion pair HPLC - mass spectrometry of nucleic acids. [Apffel, A.; Chakel, J.A.; Fischer, S.; Lichtenwalter, K.; Hancock, W.S., Analysis of oligonucleotides by HPLC-electrospray ionization mass spectrometry. "Anal. Chem", 1997,(69), pp. 1320-1325.] It has also found use in biochemistry to solubilize peptides. Industrially hexafluoro-2-propanol is used as an intermediate for pharmaceuticals (anesthetics) and agrochemicals or as a solvent and cleaner in electronics.

afety

Hexafluoro-2-propanol is a corrosive and is therefore destructive to tissues of the mucous membranes, upper respiratory tract, skin and eyes, resulting in burns or ulceration. Overexposure by inhalation may result in spasm, inflammation, chemical pneumonitis and larynx, bronchi or pulmonary edema. In case of contact with eyes corneal and conjunctival ulceration or blindness may result. Hexafluoro-2-propanol is not considered carcinogenic, but the effects of a chronic exposure are unknown.

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