Hexafluoroisopropanol

Structural formula
General
Surname	1,1,1,3,3,3-hexafluoro-2-propanol
other names	Hexafluoroisopropanol; Hexafluoropropan-2-ol; HFIP; HFP;
Molecular formula	C 3 H 2 F 6 O
Brief description	colorless liquid
External identifiers / databases
EC number	213-059-4
ECHA InfoCard	100,011,873
PubChem	13529
Wikidata	Q1123466
properties
Molar mass	168.04 g mol −1
Physical state	liquid
density	1.596 g cm −3 (20 ° C)
Melting point	−4 ° C
boiling point	58.2 ° C
Vapor pressure	160 h Pa (20 ° C)
solubility	soluble in water
safety instructions
H and P phrases	H: 314-302-332-335
	P: 280-260-304 + 340-301 + 330 + 331-305 + 351 + 338-309 + 311
Toxicological data	1500 mg kg −1 ( LD 50 , rat , oral )
Global warming potential	221 (based on 100 years)
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Hexafluoroisopropanol or hexafluoro-2-propanol , or HFIP for short , is an organic compound with the formula (CF ₃ ) ₂ CHOH. This fluorinated alcohol is used as a solvent . The colorless, volatile liquid is characterized by a strong, pungent odor. HFIP is miscible with water, methanol , 2-propanol and hexanes , but immiscible with acetonitrile . HFIP reacts as a weak acid in water because the electron-withdrawing CF ₃ groups increase the acidity of the OH group .

Hexafluoroisopropanol as a solvent is characterized by a high polarity (E ^N_T = 1.07) and as a strong hydrogen bond donor. However, it is only a weak hydrogen bridge acceptor and has a low nucleophilicity.

synthesis

Hexafluoroisopropanol, by hydrogenation of hexafluoroacetone be won.

{\ displaystyle \ mathrm {(CF_ {3}) _ {2} CO + H_ {2} \ longrightarrow (CF_ {3}) _ {2} CHOH}}

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h data sheet 1,1,1,3,3,3-hexafluoro-2-propanol (PDF) from Carl Roth , accessed on March 26, 2014.
↑ Data sheet 1,1,1,3,3,3-hexafluoro-2-propanol (PDF) from Merck , accessed on March 26, 2014.
↑ G. Myhre, D. Shindell et al .: Climate Change 2013: The Physical Science Basis . Working Group I contribution to the IPCC Fifth Assessment Report. Ed .: Intergovernmental Panel on Climate Change . 2013, Chapter 8: Anthropogenic and Natural Radiative Forcing, pp. 24-39; Table 8.SM.16 ( PDF ).
↑ A. Apffel, JA Chakel, S. Fisher, K. Lichtenwalter, WS Hancock: Analisis of Oligonucleotides by HPLC-Electrospray Ionization Mass Spectroscopy. In: Anal. Chem. 69, 1997, pp. 1320-1325.
↑ Jean-Pierre Begue, Daniele Bonnet-DELPON, Benoit Crousse: Fluorinated Alcohols: A New Medium for Selective Reaction and Clean . In: SYNLETT . 2004.
↑ Patent US4314087 : Methods of synthesizing hexafluoroisopropanol from impure mixtures and synthesis of a fluoromethyl ether therefrom. Filed December 26, 1979 , published February 2, 1982 , Applicant: Baxter Travenol Laboratories, Inventor: Phillip C. Radlick. ‌

[ROTH-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h data sheet 1,1,1,3,3,3-hexafluoro-2-propanol (PDF) from Carl Roth , accessed on March 26, 2014.

[Merck-2] Data sheet 1,1,1,3,3,3-hexafluoro-2-propanol (PDF) from Merck , accessed on March 26, 2014.

[3] G. Myhre, D. Shindell et al .: Climate Change 2013: The Physical Science Basis . Working Group I contribution to the IPCC Fifth Assessment Report. Ed .: Intergovernmental Panel on Climate Change . 2013, Chapter 8: Anthropogenic and Natural Radiative Forcing, pp. 24-39; Table 8.SM.16 ( PDF ).

[4] A. Apffel, JA Chakel, S. Fisher, K. Lichtenwalter, WS Hancock: Analisis of Oligonucleotides by HPLC-Electrospray Ionization Mass Spectroscopy. In: Anal. Chem. 69, 1997, pp. 1320-1325.

[5] Jean-Pierre Begue, Daniele Bonnet-DELPON, Benoit Crousse: Fluorinated Alcohols: A New Medium for Selective Reaction and Clean . In: SYNLETT . 2004.

[6] Patent US4314087 : Methods of synthesizing hexafluoroisopropanol from impure mixtures and synthesis of a fluoromethyl ether therefrom. Filed December 26, 1979 , published February 2, 1982 , Applicant: Baxter Travenol Laboratories, Inventor: Phillip C. Radlick. ‌