1,1,1,3,3,3-hexafluoropropan-2-ol

• ChemBase ID: 6506
• Molecular Formular: C3H2F6O
• Molecular Mass: 168.0377992
• Monoisotopic Mass: 168.000984
• SMILES: FC(C(C(F)(F)F)O)(F)F
• Canonical SMILES: OC(C(F)(F)F)C(F)(F)F
• InChI: InChI=1S/C3H2F6O/c4-2(5,6)1(10)3(7,8)9/h1,10H
• InChIKey: BYEAHWXPCBROCE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,1,1,3,3,3-hexafluoropropan-2-ol
• IUPAC Traditional name: hexafluoroisopropanol; 1,1,1,3,3,3-hexafluoropropan-2-ol
• Synonyms: 1,1,1,3,3,3-Hexafluoro-2-propanol; 2H-Hexafluoropropan-2-ol; HFIP; 1,1,1,3,3,3-Hexafluoropropan-2-ol 99.9%; 1,1,1,3,3,3-Hexafluoro-2-propanol; 1,1,1,3,3,3-Hexafluoropropan-2-ol 99%; Hexafluoroisopropanol; HFP; 1,1,1,3,3,3-HEXAFLUORO-ISOPROPANOL; 1,1,1,3,3,3-Hexafluoroisopropanol; 1,1,1,3,3,3-Hexafluoropropan-2-ol; 六氟异丙醇; 1,1,1,3,3,3-六氟-2-丙醇; 1,1,1,3,3,3-六氟代-2-丙醇

Database IDs

• CAS Number: 920-66-1
• EC Number: 213-059-4
• MDL Number: MFCD00011651
• Beilstein Number: 1841007
• PubChem SID: 24846695; 160969813; 24859495; 24874476
• PubChem CID: 13529

CALCULATED PROPERTIES

• Acid pKa: 7.974499
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 1.44993
• LogD (pH = 7.4): 1.3489344
• Log P: 1.4513825
• Molar Refractivity: 18.8317 cm^3
• Polarizability: 7.098615 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -4 °C(lit.); -4°C; -4°C
• Boiling Point: 58°C; 59 °C(lit.); 59-60°C; 59-60°C
• Density: 1.596; 1.596 g/mL at 25 °C(lit.); 1.619; 1.62 g/ml
• Refractive Index: 1.275; 1.2750; n20/D 1.275(lit.)
• Absorption Wavelength: λ: 200 nm Amax: 0.3; λ: 240 nm Amax: 0.01

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Corrosive/Harmful; IRRITANT, CORROSIVE
• RTECS: UB6450000
• European Hazard Symbols: Corrosive (C); X
• UN Number: 1760; 2922; UN1760
• German water hazard class: 2
• Hazard Class: 8
• Packing Group: 2; II
• Australian Hazchem: 2X
• Risk Statements: 20/22-34; R:34
• Safety Statements: 26-36/37/39-45; 9-26-36/37/39-45-60; S:26-46-64-36/37/39-27/28
• Emergency Response Guidebook(ERG) Number: 154
• TSCA Listed: true; 是
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H314-H332; H314-H318-H302-H332
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 2922 8/PG 2

Product Information

• Purity: >99%; ≥99%; ≥99.0% (GC); ≥99.5%; ≥99.8%; ≥99.8% (GC); 98%; 99%; 99+%
• Grade: eluent additive for LC-MS; for GC derivatization; puriss.
• Suitability: passes test for LC-MS
• Evaporation Residue: ≤0.0005%
• Impurities: ≤0.02% water; ≤0.1% water
• Cation Traces: Al: ≤0.5 mg/kg; Ba: ≤0.1 mg/kg; Bi: ≤0.1 mg/kg; Ca: ≤0.5 mg/kg; Cd: ≤0.05 mg/kg; Co: ≤0.02 mg/kg; Cr: ≤0.02 mg/kg; Cu: ≤0.02 mg/kg; Fe: ≤0.1 mg/kg; K: ≤0.5 mg/kg; Li: ≤0.1 mg/kg; Mg: ≤0.1 mg/kg; Mn: ≤0.02 mg/kg; Mo: ≤0.1 mg/kg; Na: ≤1 mg/kg; Ni: ≤0.02 mg/kg; Pb: ≤0.1 mg/kg; Sr: ≤0.1 mg/kg; Zn: ≤0.1 mg/kg
• Shelf Life: (limited shelf life, expiry date on the label)
• λ: 1 cm path, H2O reference
• Derivatization reagent for: Acylations; Esterifications
• Linear Formula: (CF3)2CHOH

DETAILS

MP Biomedicals - 02151245

Purity: >99%
1 ml = approx. 1.62 g

Apollo Scientific Ltd - PC0877

UV absorption < 0.1nm between 200 - 400 nm. Spectrophotometric grade

Apollo Scientific Ltd - PC4750

Versatile intermediate, excellent solvent for polymers, hashigh polarity and low nucleophilicity. Ask for references.

Sigma Aldrich - 325244

Packaging
5, 25 g in glass bottle
Application
Esterification reagent for the determination of aromatic acids in tissue by GLC and electron capture detection.1Additive which accelerates the Pictet-Spengler synthesis of tetrahydroisoquinolines in water catalyzed by a Bronsted acid-surfactant combined catalyst (BASC).2

Sigma Aldrich - 105228

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Application
Fluorinated solvent which enhances the efficiency of rhodium(I)-catalyzed [4+2] intramolecular cycloaddition of ether-tethered alkynyl dienes and [5+2] cycloaddition of alkynyl vinylcyclopropanes.1
Solution-phase peptide chemistry solvent.
Packaging
5, 25, 100, 500 g in glass bottle

Sigma Aldrich - 52512

Other Notes
Solvent with high solubilizing potential for peptides and peptide intermediates1

Sigma Aldrich - 52517

Other Notes
Size-exclusion chromatography in 1,1,1,3,3,3-hexafluoro-2-propanol1

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):