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

Description

Chemical Properties 

· Formula: C₃H₂F₆O
· Formula weight : 168.04
· Melting Point : -4°
· Boiling Point : 59-60°
· Density : 1.619
· Refractive Index: 1.2750
· Sensitivity: Ambient temperatures.
· Form: Liquid
· Solubility: Miscible with water, chloroform, ether and acetone.

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):

Applications
1,1,1,3,3,3-Hexafluoro-2-propanol is used for preparing hexafluoroalcohol-functionalized methacrylate polymers for lithographic/nanopatterning materials.
It plays an important role in the Friedel-Crafts reactions due to its polarity and high ionizing power. It finds use in sample preparation for GCMS. It also catalyzes the epoxidation of cyclooctene and 1-octene with hydrogen peroxide.
It is used as a solvent for many reactions and to dissolve peptides. It is also employed to produce high-end chemicals like fluorinated surfactants, fluorinated emulsifier and fluorinated medicine. It acts as a cleaner in electronic industry.

Notes
Incompatible with strong oxidizing agents, strong acids, strong bases, aluminum, zinc and alkali metals.

Other References:
Beilstein : 1841007
UN# : UN2922


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.

위험 및 안전 코드

· 위험 문구 : 20/22-34

Harmful by inhalation and if swallowed.Causes burns.

· 안전 문구 : 9-26-36/37/39-45-60

Keep container in a well-ventilated place.In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.Wear suitable protective clothing, gloves and eye/face protection.In case of accident or if you feel unwell, seek medical advice immediately (show the label where possible).This material and its container must be disposed of as hazardous waste

· ​TSCA : 예

· ​RTECS: UB6450000