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325244

Sigma-Aldrich

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

≥99.5%

Synonym(s):

HFP, Hexafluoroisopropanol

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About This Item

Linear Formula:
(CF3)2CHOH
CAS Number:
920-66-1
Molecular Weight:
168.04
Beilstein:
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

Signal Word

Danger

Hazard Statements

H314,H361,H373

Hazard Classifications

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

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 2

Flash Point(F)

closed cup - boils before flash

Flash Point(C)

closed cup - boils before flash

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Amit U Joshi et al.
Nature neuroscience, 22(10), 1635-1648 (2019-09-26)
In neurodegenerative diseases, debris of dead neurons are thought to trigger glia-mediated neuroinflammation, thus increasing neuronal death. Here we show that the expression of neurotoxic proteins associated with these diseases in microglia alone is sufficient to directly trigger death of
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