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184225

Sigma-Aldrich

Hydrogen fluoride pyridine

pyridine ~30 %, hydrogen fluoride ~70 %

Synonym(s):

HF-Pyridine, Olah′s reagent, PPHF, Poly(pyridine fluoride), Pyridine hydrofluoride, Pyridinium poly(hydrogen fluoride), Pyridinium polybifluoride

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About This Item

CAS Number:
62778-11-4
Beilstein:
4750151
MDL number:
MFCD00012436
UNSPSC Code:
12352301
PubChem Substance ID:
24851101
NACRES:
NA.22

form

liquid

Quality Level

200

composition

hydrogen fluoride, ~70%
pyridine, ~30%

density

1.1 g/mL at 20 °C (lit.)

storage temp.

−20°C

SMILES string

F[H].c1ccncc1

InChI

1S/C5H5N.FH/c1-2-4-6-5-3-1;/h1-5H;1H

InChI key

GRJJQCWNZGRKAU-UHFFFAOYSA-N

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General description

May contain or form low levels of calcium fluoride during storage. Presence of this does not impact the specification values.

Application

Convenient form of anhydrous HF, stable up to 50°C. Has been used for the preparation of β-fluoroamines from amino alcohols and for the fluorination of acetylenes.
Used together with hypervalent iodine(III) reagents for ipso-fluorination of para-substituted phenols providing cyclohexadienones. Employed with Selectfluor™ (Catalog No. 439479) for geminal fluorination of 2,2-diaryl-1,3-dithiolanes.
Reactant for preparation of:
  • Epimers of shikimic acid with the features of fucosylated glycans via zinc-mediated reductive ring opening followed by a Barbier reaction
  • Vaccinia H1-related (VHR) phosphatase inhibitor with a nonacidic phosphate-mimicking core structure
  • Candidates for nucleic acid drugs
  • ω-substituted gem-difluoroalkanes by oxidative desulfurization-difluorination

Reagent for:
  • Halofluorination reactions

Legal Information

Selectfluor is a registered trademark of Merck KGaA, Darmstadt, Germany
Sure/Pac is a trademark of Sigma-Aldrich Co. LLC

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H300 + H310 + H330,H314

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Eye Dam. 1 - Skin Corr. 1A

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

非剧毒-急性毒性1

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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Journal of Fluorine Chemistry, 37, 343-343 (1987)
Tetrahedron Letters, 32, 69-69 (1991)
Tetrahedron, 60, 6629-6629 (2004)
V Prakash Reddy et al.
Chemical communications (Cambridge, England), (5), 654-656 (2005-01-27)
2,2-diaryl-1,3-dithiolanes, readily obtainable from diaryl ketones, were transformed into the corresponding gem-difluoro compounds using a novel reagent combination involving Selectfluor and pyridinium polyhydrogen fluoride (PPHF) under mild conditions in moderate to good yields.
Hui Shen et al.
Infection and immunity, 83(7), 2694-2704 (2015-04-22)
Fungi can shield surface pathogen-associated molecular patterns (PAMPs) for evading host immune attack. The most common and opportunistic human pathogen, Candida albicans, can shield β-(1 3)-glucan on the cell wall, one of the major PAMPs, to avoid host phagocyte Dectin-1
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