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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

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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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

Certificates of Analysis (COA)

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. What is Product 105228, 1,1,1,3,3,3-Hexafluoro-2-propanol, soluble in?

    According to literature, 1,1,1,3,3,3-Hexafluoro-2-propanol is soluble in 100% ethanol (to 10% v/v), which will yield colorless solution, chloroform, and water.

  4. What is the vapor pressure of Product 105228, 1,1,1,3,3,3-Hexafluoro-2-propanol?

    The vapor pressure of this product has been reported as 42.1 mbar at 0 degrees C.

  5. How should Product 105228, 1,1,1,3,3,3-Hexafluoro-2-propanol, be stored?

    1,1,1,3,3,3-Hexafluoro-2-propanol should be stored in a cooler prior to opening since this product evaporates quickly and this will relieve pressure within the bottle.

  6. Can Product 105228, 1,1,1,3,3,3-Hexafluoro-2-propanol, be used as a solution phase peptide chemistry solvent?

    This product is a solution phase peptide chemistry solvent an that applications has been cited in literature.  A specific reference would be:  Biochem. 29, 2639 (1990).

  7. What type of gloves should be worn while handling Product 105228, 1,1,1,3,3,3-Hexafluoro-2-propanol?

    We would recommend using neoprene gloves while handling this compound.

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  9. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  10. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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)
Akio Saito et al.
The Journal of organic chemistry, 71(17), 6437-6443 (2006-08-12)
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.
Rita Sobreiro-Almeida et al.
Materials science & engineering. C, Materials for biological applications, 103, 109866-109866 (2019-07-28)
Kidney diseases are recognized as a major health problem, which affect 10% of the population. Because currently available therapies have many limitations, some tissue engineering strategies have been emerging as promising approaches in this field. In this work, porcine kidneys
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)

Articles

Hexafluoroalcohol-functionalized methacrylate monomers for lithographic/nanopatterning materials

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