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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

Stock No. Size Price ($) Quantity Availability
A12747-06 5g 38.70
A12747-14 25g 99.50
A12747-22 100g 250.00
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1,1,1,3,3,3-Hexafluoro-2-propanol, 99+%

MDL
MFCD00011651
EINECS
213-059-4

Chemical Properties

Formula
C3H2F6O
Formula Weight
168.04
Melting point
-4°
Boiling Point
59-60°
Density
1.619
Refractive Index
1.2750
Storage & Sensitivity
Ambient temperatures.
Solubility
Miscible with water, chloroform, ether and acetone.

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.

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):

Pal, U.; Sen, S.; Maiti, N. C. Calpha-H Carries Information of a Hydrogen Bond Involving the Geminal Hydroxyl Group: A Case Study with a Hydrogen-Bonded Complex of 1,1,1,3,3,3-Hexafluoro-2-propanol and Tertiary Amines. J. Phys. Chem. A 2014, 118 (6), 1024-1030.

Wang, L.; Wang, J.-W.; Cui, A.-j.; Cai, X.-X.; Wan, Y.; Chen, Q.; He, M.-Y.; Zhang, W. Regioselective 2,6-dihalogenation of BODIPYs in 1,1,1,3,3,3-hexafluoro-2-propanol and preparation of novel meso-alkyl polymeric BODIPY dyes. RSC Adv. 2013, 3, 9219-9222.

GHS Hazard and Precautionary Statements

Hazard Statements: H302+H312+H332-H314-H335

Harmful if swallowed. Harmful in contact with skin. Harmful if inhaled. Causes severe skin burns and eye damage. May cause respiratory irritation.

Precautionary Statements: P260-P264b-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P501c

Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT induce vomiting. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

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

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