A12747

1,1,1,3,3,3-Hexafluoro-2-propanol, 99+%

CAS Number 920-66-1 Synonyms
  • 1,1,1,3,3,3-Hexafluoroisopropanol
  • HFIP

 
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1,1,1,3,3,3-Hexafluoro-2-propanol, 99+%

MDL: MFCD00011651
EINECS: 213-059-4

Chemical Properties

Formula: C3H2F6O  Boiling point: 59-60°
Formula weight: 168.04  Density: 1.619
Melting point: -4° Refractive Index: 1.2750

Literature 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 (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).

Lithiation generates the useful synthon lithium perfluoropropenolate: Org. Synth., 76, 151 (1998):

GHS Hazard and Precautionary Statements

Hazard Statements : H314-H318-H302-H332

Causes severe skin burns and eye damage. Causes serious eye damage. Harmful if swallowed. Harmful if inhaled.

Precautionary Statements : P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A

Do not breathe dust/fume/gas/mist/vapours/spray. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

CorrosiveHarmful or Irritant

Other References

Beilstein: 1841007
UN#: UN1760
Hazard Class: 8
Packing Group: II
Harmonized Tariff Code: 2905.59
TSCA: Yes
RTECS: UB6450000

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