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Sigma-Aldrich

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

≥99.5%

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Synonym(s):
HFP, Hexafluoroisopropanol
Linear Formula:
(CF3)2CHOH
CAS Number:
920-66-1
Molecular Weight:
168.04
Beilstein/REAXYS Number:
1841007
EC Number:
213-059-4
MDL number:
MFCD00011651
UNSPSC Code:
12352104
PubChem Substance ID:
24859495

assay

≥99.5%

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 (HFIP) is an efficient hydrogen-bond donor and highly polar solvent for a reactions with Si-capped Π donors. HFIP is a solvent and its ability to induce self-assembly of an aromatic dipeptide was evaluated. HFIP-induced coacervation in aqueous mixed systems of catanionic surfactants of dodecyltrimethylammonium bromide (DTAB) and sodium dodecyl sulfate (SDS) was investigated.

Application

1,1,1,3,3,3-Hexafluoro-2-propanol (Hexafluoroisopropanol) was used as:
  • a crucial additive to improve the enantioselectivity of Friedel-Crafts alkylation of pyrrole with isatins
  • esterification reagent for the determination of aromatic acids in tissue by GLC and electron capture detection
  • additive which accelerates the Pictet-Spengler synthesis of tetrahydroisoquinolines in water catalyzed by a Bronsted acid-surfactant combined catalyst (BASC)

pictograms

Health hazardCorrosion
GHS08,GHS05

signalword

Danger

Hazard Classifications

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

wgk_germany

WGK 2

flash_point_f

closed cup

flash_point_c

closed cup

ppe

Faceshields, Gloves, Goggles

Certificates of Analysis (COA)

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Tetrahedron Letters, 48, 835-835 (2007)
Paul A Novick et al.
Journal of medicinal chemistry, 55(7), 3002-3010 (2012-03-17)
Drug design studies targeting one of the primary toxic agents in Alzheimer's disease, soluble oligomers of amyloid β-protein (Aβ), have been complicated by the rapid, heterogeneous aggregation of Aβ and the resulting difficulty to structurally characterize the peptide. To address
Chong Li et al.
Organic letters, 16(12), 3192-3195 (2014-06-10)
The highly enantioselective Friedel-Crafts alkylation of pyrrole with isatins catalyzed by the tridentate Schiff base/Cu catalyst was developed. Hexafluoroisopropanol (HFIP) was used as a crucial additive to improve the enantioselectivity. In the case of N-unprotected isatins, an innovative substrate slow-releasing
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)
Benjamin H Rotstein et al.
Chemical communications (Cambridge, England), 48(31), 3775-3777 (2012-03-21)
A novel class of reagents, thioester isocyanides, have been prepared and applied in the synthesis of peptide macrocycles. The isocyanide part of the molecule is deployed in a multicomponent macrocyclization step. This step is followed by chemoselective peptide ligation at
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