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 = &minus;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]]