Hexafluoro-2-propanol

1,1,1,3,3,3-Hexafluoro-2-propanol

Names
IUPAC names 1,1,1,3,3,3-Hexafluoro -2-propanol
Other names Hexafluoroisopropanol, Hexafluoroisopropyl alcohol, HFIP
Identifiers
CAS Number	920-66-1 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:63104 N
ChemSpider	10606755 Y
ECHA InfoCard	100.011.873
PubChem CID	13529
RTECS number	UB6450000
InChI InChI=1S/C3H2F6O/c4-1(5)2(6,10)3(7,8)9/h1,10H Y Key: NMFQPFSIPWZZMR-UHFFFAOYSA-N Y InChI=1S/C3H2F6O/c4-2(5,6)1(10)3(7,8)9/h1,10H Key: BYEAHWXPCBROCE-UHFFFAOYSA-N
SMILES C(C(F)(F)F)(C(F)(F)F)O
Properties
Chemical formula	C3H2F6O
Molar mass	168.04 g·mol−1
Appearance	Colorless liquid
Density	1.596 g/mL
Melting point	−3.3 °C (26.1 °F; 269.8 K)
Boiling point	58.2 °C (136.8 °F; 331.3 K)
Solubility in water	Miscible
Vapor pressure	16 kPa at 20 °C
Viscosity	1.65 cP at 20 °C
Hazards
Main hazards	Corrosive (C)
Safety data sheet	External MSDS
R-phrases	R20/22, R34, R41
S-phrases	S26, S36/37/39, S45
NFPA 704	0 3 0
Flash point	> 100 °C (212 °F; 373 K)
Related compounds
Related Organofluorides; alcohols	Hexafluoroacetone; Isopropyl alcohol, 2,2,2-Trifluoroethanol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Hexafluoroisopropanol, commonly abbreviated HFIP, is the organic compound with the formula (CF₃)₂CHOH. This fluorinated alcohol finds use as solvent and synthetic intermediate. It appears as a colorless, volatile liquid that is characterized by a strong, pungent odor. As a solvent hexafluoro-2-propanol is polar and 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 transparent to UV light with high density, low viscosity and low refractive index.

Hexafluoro-2-propanol is prepared from hexafluoropropylene via hexafluoroacetone, which is reduced by catalytic hydrogenation or by hydride reagents.

Hexafluoro-2-propanol is a speciality solvent for some polar polymers and organic synthesis. It is especially effective for solubilizing 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. It has also found use in biochemistry to solubilize peptides and to monomerize β-sheet protein aggregates. 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.