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Merck
CN

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

Key Documents

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Product Name

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

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

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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

General description

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

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

Regulatory Information

监管及禁止进口产品
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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 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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