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Merck

184225

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

UNSPSC Code:
12352301
NACRES:
NA.22
PubChem Substance ID:
24851101
MDL number:
MFCD00012436
Beilstein/REAXYS Number:
4750151

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InChI

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

SMILES string

F[H].c1ccncc1

InChI key

GRJJQCWNZGRKAU-UHFFFAOYSA-N

form

liquid

composition

hydrogen fluoride, ~70% , pyridine, ~30%

density

1.1 g/mL at 20 °C (lit.)

storage temp.

−20°C

Quality Level

200

Related Categories

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

pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

signalword

Danger

Hazard Classifications

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

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX8638
MKCX8637
MKCV8676
MKCS3418
MKCP3725

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Journal of Fluorine Chemistry, 37, 343-343 (1987)
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.
Tetrahedron Letters, 32, 69-69 (1991)
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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