Hexafluoro-2-propanol
1619291
172335149
2007-11-18T19:53:45Z
Smokefoot
698909
rm redlink
{{Chembox new
| Name = 1,1,1,3,3,3-Hexafluoro-2-propanol
| ImageFile = Hexafluoroisopropanol.svg
| ImageFile2 = Hexafluoroisopropanol 3D.png
<!-- | ImageSize = 200px -->
| ImageName = 1,1,1,3,3,3-Hexafluoro-2-propanol
| IUPACName = 1,1,1,3,3,3-Hexafluoro<br />-2-propanol
| OtherNames = Hexafluoroisopropanol,<br />Hexafluoroisopropyl alcohol,<br />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 = C<sub>3</sub>H<sub>2</sub>F<sub>6</sub>O
| 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 [[Poise|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 = [[alcohol]]s
| OtherFunctn = [[Isopropyl alcohol]]<br />[[2,2,2-Trifluoroethanol]]
| Function = [[:Category:Organofluorides|organofluoride]]s
| OtherFunctn = [[Hexafluoroacetone|Hexafluoro-2-propanone]]
}}
}}
'''Hexafluoroisopropanol''', commonly abbreviated HFIP is the [[organic compound]] with the [[chemical formula|formula]] (CF<sub>3</sub>)<sub>2</sub>CHOH. This
[[fluorine|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 [[ultraviolet|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.<ref name=Gunt>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.</ref>
:(CF<sub>3</sub>)<sub>2</sub>CO + H<sub>2</sub> → (CF<sub>3</sub>)<sub>2</sub>CHOH
==Uses==
Hexafluoro-2-propanol is a specialty solvent in [[organic synthesis]]<ref> ''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.</ref><ref> ''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</ref> 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 [[polyamide]]s, [[polyacrylonitrile]]s, polyacetals, [[polyester]]s (e.g. [[polyglycolide]]), and polyketones. Because of its acidity (pK<sub>a</sub> = 9.3), it can be used as acid in volatile buffers for ion pair [[HPLC]] - [[mass spectrometry]] of [[nucleic acid]]s.<ref>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.</ref>
It has also found use in [[biochemistry]] to solubilize [[peptide]]s. Industrially hexafluoro-2-propanol is used as an intermediate for pharmaceuticals ([[anesthetic]]s) and agrochemicals or as a solvent and cleaner in electronics.
==Safety==
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.
==References==
===Notes===
{{Reflist}}
===Sources===
<div class=references-small>
* {{cite web | last = Radlick | first = Phillip C | title = Methods of synthesizing hexafluoroisopropanol from impure mixtures and synthesis of a fluoromethyl ether therefrom | work = United States Patent 4,314,087 | date = [[1982-02-02]] | url = http://www.freepatentsonline.com/4314087.html | accessdate = 2006-10-18 }}
* {{cite web | last = Cheminal | first = Bernard | coauthors = H. Mathais and M. Thomarat | title = Process for the synthesis of 2,2,2-trifluoroethanol and 1,1,1,3,3,3-hexafluoroisopropanol | work = United States Patent 4,647,706 | date = [[1987-03-03]] | url = http://www.freepatentsonline.com/4647706.html | accessdate = 2006-10-18 }}
* {{cite web | title = Hexafluoroisopropanol datasheet | publisher = [[DuPont]] | url = http://www.dupont.com/polymerspecialties/HFIP.html | accessdate = 2006-10-18 }}
</div>
[[Category:Organofluorides]]
[[Category:Halogenated solvents]]
[[Category:Alcohols]]
[[it:Esafluoro-2-propanolo]]