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105228

Sigma-Aldrich

1,1,1,3,3,3-Hexafluoro-2-propanol

≥99%

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Synonym(s):
HFP, Hexafluoroisopropanol
Linear Formula:
(CF3)2CHOH
CAS Number:
Molecular Weight:
168.04
Beilstein:
1841007
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

≥99%

refractive index

n20/D 1.275 (lit.)

bp

59 °C (lit.)

mp

−4 °C (lit.)

density

1.596 g/mL at 25 °C (lit.)

SMILES string

OC(C(F)(F)F)C(F)(F)F

InChI

1S/C3H2F6O/c4-2(5,6)1(10)3(7,8)9/h1,10H

InChI key

BYEAHWXPCBROCE-UHFFFAOYSA-N

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This Item
181278.045151612594
Sevoflurane Related Compound C United States Pharmacopeia (USP) Reference Standard

USP

1612594

Sevoflurane Related Compound C

refractive index

n20/D 1.275 (lit.)

refractive index

n20/D 1.275 (lit.)

refractive index

-

refractive index

n20/D 1.275 (lit.)

bp

59 °C (lit.)

bp

59 °C (lit.)

bp

58 °C/1013 hPa

bp

59 °C (lit.)

mp

−4 °C (lit.)

mp

−4 °C (lit.)

mp

-3 °C

mp

−4 °C (lit.)

density

1.596 g/mL at 25 °C (lit.)

density

1.596 g/mL at 25 °C (lit.)

density

1.62 g/cm3 at 20 °C

density

1.596 g/mL at 25 °C (lit.)

General description

1,1,1,3,3,3-Hexafluoro-2-propanol is a solution-phase peptide chemistry solvent. This fluorinated polar solvent of high ionizing power facilitates Friedel–Crafts-type reactions, using covalent reagents in the absence of a Lewis acid catalyst. It also enhances the efficiency of rhodium(I)-catalyzed [4+2] intramolecular cycloaddition of ether-tethered alkynyl dienes and [5+2] cycloaddition of alkynyl vinylcyclopropanes. 1,1,1,3,3,3-Hexafluoro-2-propanol clusters catalyzes the epoxidation of cyclooctene and 1-octene with hydrogen peroxide.

Application

1,1,1,3,3,3-Hexafluoro-2-propanol was used for preparing hexafluoroalcohol-functionalized methacrylate polymers for lithographic/nanopatterning materials.

Pictograms

CorrosionHealth hazard

Signal Word

Danger

Hazard Statements

Hazard Classifications

Eye Dam. 1 - Repr. 2 - Skin Corr. 1A - STOT RE 2

Storage Class Code

8B - Non-combustible, corrosive hazardous materials

WGK

WGK 2

Flash Point(F)

No data available

Flash Point(C)

No data available

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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In fluorinated alcohols, the cationic Rh(I) species, which is derived from [Rh(COD)Cl]2 and AgSbF6, efficiently catalyzed intramolecular [4+2] cycloaddition reactions of ester-tethered 1,3-diene-8-yne derivatives. The catalytic system was also effective in intramolecular [5+2] cycloaddition reactions of ester-tethered omega-alkynyl vinylcyclopropane compounds.
Hexafluoroalcohol-functionalized Methacrylate Monomers for Lithographic/Nanopatterning Materials.
Sanders DP, et al.
Material Matters, 6(1), 1-7 (2011)
Kinetic Studies of Olefin Epoxidation with Hydrogen Peroxide in 1, 1, 1, 3, 3, 3-Hexafluoro-2-propanol Reveal a Crucial Catalytic Role for Solvent Clusters.
Berkessel A and Adrio JA.
Advanced Synthesis & Catalysis, 346(2-3), 275-280 (2004)
Lewis acid catalyst free electrophilic alkylation of silicon-capped pi donors in 1,1,1,3,3,3-hexafluoro-2-propanol.
Maxim O Ratnikov et al.
Angewandte Chemie (International ed. in English), 47(50), 9739-9742 (2008-11-05)

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