1,1,1,3,3,3-Hexafluoro-2-propanol

• Catalog No.: A12747
• CAS Number: 920-66-1
• M. F.: C3H2F6O
• M. W.: 168.0377992
• Purity: 99+%

SYNONYMS

• Title: 1,1,1,3,3,3-六氟代-2-丙醇
• IUPAC name: 1,1,1,3,3,3-hexafluoropropan-2-ol
• IUPAC Traditional name: hexafluoroisopropanol
• Synonyms: 1,1,1,3,3,3-Hexafluoroisopropanol; HFIP

DATABASE IDS

• EC Number: 213-059-4
• Beilstein Number: 1841007
• MDL Number: MFCD00011651
• CAS Number: 920-66-1

PROPERTIES

• Purity: 99+%
• Boiling Point: 59-60°C
• Density: 1.619
• Melting Point: -4°C
• Refractive Index: 1.2750
• GHS Hazard statements: H314-H318-H302-H332
• European Hazard Symbols: X
• European Hazard Symbols: Corrosive (C)
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A
• Risk Statements: 20/22-34
• RTECS: UB6450000
• Safety Statements: 9-26-36/37/39-45-60
• TSCA Listed: 是
• Hazard Class: 8
• UN Number: UN1760
• Packing Group: II

REFERENCES

• 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).
• 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 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.
• The mildly acidic character (pK_a 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).
• Lithiation generates the useful synthon lithium perfluoropropenolate: Org. Synth., 76, 151 (1998):