Hexafluoro-2-propanol

1,1,1,3,3,3-Hexafluoro-2-propanol
Names
	IUPAC name 1,1,1,3,3,3-Hexafluoro-propan-2-ol
	Other names Hexafluoroisopropanol,; Hexafluoroisopropyl alcohol,; HFIP
Identifiers
CAS Number	920-66-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:63104 ;
ChemSpider	10606755 ;
ECHA InfoCard	100.011.873
PubChem CID	13529;
RTECS number	UB6450000;
UNII	3D632GYQ50 ;
CompTox Dashboard (EPA)	DTXSID1022134 ;
	InChI InChI=1S/C3H2F6O/c4-1(5)2(6,10)3(7,8)9/h1,10H Key: NMFQPFSIPWZZMR-UHFFFAOYSA-N ; 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	168.038 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R-phrases (outdated)	R20/22, R34, R41
S-phrases (outdated)	S26, S36/37/39, S45
NFPA 704 (fire diamond)	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).
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	Infobox references

Hexafluoroisopropanol, commonly abbreviated HFIP, is the organic compound with the formula (CF₃)₂CHOH. This fluoroalcohol 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. (CF₃)₂CHCOH is classified as a hard Lewis acid and its acceptor properties are discussed in the ECW model. Hexafluoro-2-propanol is transparent to UV light with high density, low viscosity and low refractive index.

Production and uses

Hexafluoro-propan-2-ol is prepared from hexafluoropropylene through hexafluoroacetone, which is then hydrogenated.[1]

(CF₃)₂CO + H₂ → (CF₃)₂CHOH

Hexafluoro-propan-2-ol is a speciality solvent for some polar polymers and organic synthesis.[2][3] 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.[4]

Medicine

It is both the precursor and the chief metabolite of the inhalation anesthetic sevoflurane.

Safety

Hexafluoro-2-propanol is a volatile, corrosive liquid that can cause severe burns and respiratory problems.[5]

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References

Notes

Günter Siegemund, Werner Schwertfeger, Andrew Feiring, Bruce Smart, Fred Behr, Herward Vogel, Blaine McKusick “Fluorine Compounds, Organic” in Ullmann's Encyclopedia of Industrial Chemistry, John Wiley & Sons, 2007. doi:10.1002/14356007.a11_349
Bégué, J.-P.; Bonnet-Delpon, D.; Crousse, B. (2004). "Fluorinated Alcohols: A New Medium for Selective and Clean Reaction". Synlett (1): 18–29. doi:10.1055/s-2003-44973.
Shuklov, Ivan A.; Dubrovina, Natalia V.; Börner, Armin (2007). "Fluorinated Alcohols as Solvents, Cosolvents and Additives in Homogeneous Catalysis". Synthesis: 2925–2943. doi:10.1055/s-2007-983902.
Apffel, A.; Chakel, J.A.; Fischer, S.; Lichtenwalter, K.; Hancock, W.S. (1997). "Analysis of oligonucleotides by HPLC-electrospray ionization mass spectrometry". Anal. Chem. 69: 1320–1325. doi:10.1021/ac960916h.
"HFIP MSDS". Fisher Scientific. Retrieved 2014-08-18.

Sources

Radlick, Phillip C (1982-02-02). "Methods of synthesizing hexafluoroisopropanol from impure mixtures and synthesis of a fluoromethyl ether therefrom". United States Patent 4,314,087. Retrieved 2006-10-18.
Cheminal, Bernard; H. Mathais; M. Thomarat (1987-03-03). "Process for the synthesis of 2,2,2-trifluoroethanol and 1,1,1,3,3,3-hexafluoroisopropanol". United States Patent 4,647,706. Retrieved 2006-10-18.
"Hexafluoroisopropanol datasheet". DuPont. Archived from the original on 2006-10-08. Retrieved 2006-10-18.

External links

Application note on quantification of HFIP in polymers

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[Gunt-1] Günter Siegemund, Werner Schwertfeger, Andrew Feiring, Bruce Smart, Fred Behr, Herward Vogel, Blaine McKusick “Fluorine Compounds, Organic” in Ullmann's Encyclopedia of Industrial Chemistry, John Wiley & Sons, 2007. doi:10.1002/14356007.a11_349

[2] Bégué, J.-P.; Bonnet-Delpon, D.; Crousse, B. (2004). "Fluorinated Alcohols: A New Medium for Selective and Clean Reaction". Synlett (1): 18–29. doi:10.1055/s-2003-44973.

[3] Shuklov, Ivan A.; Dubrovina, Natalia V.; Börner, Armin (2007). "Fluorinated Alcohols as Solvents, Cosolvents and Additives in Homogeneous Catalysis". Synthesis: 2925–2943. doi:10.1055/s-2007-983902.

[4] Apffel, A.; Chakel, J.A.; Fischer, S.; Lichtenwalter, K.; Hancock, W.S. (1997). "Analysis of oligonucleotides by HPLC-electrospray ionization mass spectrometry". Anal. Chem. 69: 1320–1325. doi:10.1021/ac960916h.

[5] "HFIP MSDS". Fisher Scientific. Retrieved 2014-08-18.