Substance
ID:715853
Names and Identifiers
IUPAC name
1,1,1,3,3,3-hexafluoropropan-2-ol
IUPAC Traditional name
hexafluoroisopropanol
Synonyms
HFIP1,1,1,3,3,3-Hexafluoro-2-propanol1,1,1,3,3,3-Hexafluoroisopropanol1,1,1,3,3,3-六氟代-2-丙醇
Registration numbers
Beilstein Number
EC Number
MDL Number
CAS Number
Properties
Product Information
Purity
99+%
Safety Information
Safety Statements
9-26-36/37/39-45-60
Hazard Class
8
Risk Statements
20/22-34
TSCA Listed
是
GHS Hazard statements
H314-H318-H302-H332
European Hazard Symbols
Corrosive (C)
Harmful (X)GHS Precautionary statements
P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A
RTECS
UB6450000
GHS Pictograms
Acute toxicity (oral, dermal, inhalation), category 4
Skin irritation, category 2
Eye irritation, category 2
Skin sensitisation, category 1
Specific Target Organ Toxicity – Single exposure, category 3
Corrosive to metals, category 1
Skin corrosion, categories 1A,1B,1C
Serious eye damage, category 1
Packing Group
II
UN Number
UN1760
Physical Property
Boiling Point
59-60°C
Density
1.619
Melting Point
-4°C
Refractive Index
1.2750
Molecule Details
No Data Available
Click here to submit data
Molecular Spectra
No Data Available
Click here to submit data
References
• The esters formed with N-protected amino acids have been investigated as active intermediates in peptide synthesis: J. Org. Chem., 44, 4577 (1979). See Appendix 6.
• Effective solvent for uncatalyzed epoxidations of alkenes with H2O2 (caution! 60%): Synlett, 248 (2001); or, more conveniently, Urea hydrogen peroxide adduct, L13940: Eur. J. Org. Chem., 3290 (2002). Superior reaction medium for epoxidations, catalyzed by Hexafluoroacetone trihydrate, L10777: Synlett, 1305 (2001). An efficient, selective oxidation of sulfides to sulfoxides with 30% H2O2 employs HFIP as solvent, avoiding over-oxidation to the sulfone: Tetrahedron Lett., 39, 3141 (1998). For a review of fluorinated alcohols as solvents for selective and clean reactions, see: Synlett, 18 (2004).
• The mildly acidic character (pKa 9.3) has been exploited in the selective deprotection of the 4,4'-dimethoxytrityl group in acid-sensitive nucleosides and nucleotides without competing N-glycosyl cleavage: Tetrahedron Lett., 36, 7833 (1995).
• Valuable solvent of high polarity and low nucleophilicity: Tetrahedron Lett., 2335 (1974). Extremely powerful H bond donor but poor H bond acceptor: anions are highly solvated, but cations poorly. For feature article on the use of this unique solvent in the stabilization of radical cations, with particular application to EPR spectroscopy, see: Chem. Commun., 2105 (1996). Preferred solvent for the direct substitution of phenol ethers promoted by [Bis(trifluoroacetoxy)iodo]benzene, L15141: Tetrahedron Lett., 32, 4321 (1991). The intermediacy of radical cations in this reaction has been demonstrated: J. Am. Chem. Soc., 116, 3684 (1994). See also: J. Org. Chem., 60, 7144 (1995).
• Powerful solvent for oligopeptides: Bull. Chem. Soc. Jpn., 61, 281 (1984); 66, 494 (1993). Used alone as a peptide coupling medium, HFIP gives poor results, but as a cosolvent along with proton acceptors such as DMF, good results, with improved peptide solubility, can be obtained: Tetrahedron Lett., 33, 7007 (1992).
• Lithiation generates the useful synthon lithium perfluoropropenolate: Org. Synth., 76, 151 (1998):
