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920-66-1 - 1,1,1,3,3,3-Hexafluoro-2-propanol, 99+% - 1,1,1,3,3,3-Hexafluoroisopropanol - HFIP - A12747 - Alfa Aesar

A12747 1,1,1,3,3,3-Hexafluoro-2-propanol, 99+%

CAS-Nummer
920-66-1
Synonyme
1,1,1,3,3,3-Hexafluoroisopropanol
HFIP

Größe Preis ($) Menge Verfügbarkeit
5g 31,86
25g 82,89
100g 232,78
Zum Warenkorb hinzufügen Zur Angebotsanfrage hinzufügen Artikel anzeigen

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

MDL
MFCD00011651
EINECS
213-059-4

Chemische Eigenschaften

Formel
C3H2F6O
Molmasse
168.04
Schmelzpunkt
-4°
Siedepunkt
59-60°
Dichte
1.619
Brechungsindex
1.2750
Löslichkeit
Miscible with water, chloroform, ether and acetone.

Anwendungen

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.

Bemerkungen

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

Literaturverweise

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 Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H314-H318-H302-H332

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

Sicherheitshinweise: P260-P261-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Avoid breathing dust/fume/gas/mist/vapours/spray. 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 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. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Immediately call a POISON CENTER or doctor/physician. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Weitere Referenzen

Beilstein
1841007
Gefahrenklasse
8
Verpackungsgruppe
II
Harmonized Tariff Code
2905.59
TSCA
Yes
RTECS
UB6450000

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