pyridine hydrofluoride

• ChemBase ID: 8093
• Molecular Formular: C5H6FN
• Molecular Mass: 99.1062432
• Monoisotopic Mass: 99.04842742
• SMILES: c1cnccc1.F
• Canonical SMILES: c1cccnc1.F
• InChI: InChI=1S/C5H5N.FH/c1-2-4-6-5-3-1;/h1-5H;1H
• InChIKey: GRJJQCWNZGRKAU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: pyridine hydrofluoride
• IUPAC Traditional name: pyridine hydrofluoride
• Synonyms: Olah′s reagent; PPHF; Poly(pyridine fluoride); Pyridinium poly(hydrogen fluoride); Pyridinium polybifluoride; HF-Pyridine; Pyridine hydrofluoride; Hydrogen fluoride pyridine; Hydrogen fluoride/pyridine (55% HF); Hydrogen fluoride-pyridine (70% HF); Olah's Reagent; Hydrogen fluoride/pyridine (70% HF); Hydrogen fluoride pyridine complex; pyridine hydrofluoride; HF-吡啶; 氟化氢吡啶; 吡啶氢氟酸盐; 氟化氢吡啶络合物

Database IDs

• CAS Number: 32001-55-1; 62778-11-4
• MDL Number: MFCD00012436
• Beilstein Number: 4750151
• Merck Index: 146821
• PubChem SID: 24851101; 160971400
• PubChem CID: 64774

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.6230428
• LogD (pH = 7.4): 0.75354445
• Log P: 0.7555734
• Molar Refractivity: 23.9011 cm^3
• Polarizability: 9.4423685 Å^3
• Polar Surface Area: 12.89 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 50°C/1mm; 50°C/1mm
• Flash Point: none°C
• Density: 1.1; 1.1 g/mL at 20 °C(lit.); 1.100
• Hydrophobicity(logP): 0.645

Safety Information

• Storage Warning: Moisture Sensitive; MOISTURE SENSITIVE, KEEP COLD, TOXIC, CORROSIVE; Toxic; Very Toxic/Corrosive/Keep Cold
• European Hazard Symbols: Toxic (T); Highly toxic (T+)
• UN Number: 1790; UN1790
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 1; I
• Risk Statements: 26/27/28-35
• Safety Statements: 26-28-36/37/39-45
• TSCA Listed: true; 否
• GHS Pictograms: GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H314-H330; H300-H310-H330-H314-H318
• GHS Precautionary statements: P260-P264-P280-P284-P301 + P310-P302 + P350; P260-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P361-P405-P501A
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1790 8/PG 1
• Storage Temperature: -20°C

Product Information

• Purity: 95%; ca 70% HF
• Compostion: hydrogen fluoride, ~70%; pyridine, ~30%
• Linear Formula: C5H5N · (HF)x

DETAILS

Apollo Scientific Ltd - PC4828

Convenient form of anhy. HF for hydrofluorination & halo-fluorination of alkenes and alkynes, ask for references.. Packaged in Nalgene bottles

Sigma Aldrich - 184225

General description
May contain or form low levels of calcium fluoride during storage. Presence of this does not impact the specification values.
Packaging
25, 100 g in poly bottle
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.1,2Used together with hypervalent iodine(III) reagents for ipso-fluorination of para-substituted phenols providing cyclohexadienones.3 Employed with Selectfluor™ (Catalog No. 439479) for geminal fluorination of 2,2-diaryl-1,3-dithiolanes.4
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-difluorinationReagent for:
• Halofluorination reactions
Legal Information
Selectfluor is a registered trademark of Air Products & Chemicals, Inc.
Sure/Pac is a trademark of Sigma-Aldrich Co. LLC

REFERENCES

• Convenient form of anhydrous HF, showing increased reactivity in many reactions: J. Org. Chem., 44, 3872 (1979). Alkenes and alkynes undergo hydrofluorination; in the presence of NIS or NBS, iodo- or bromofluorination occurs: Synthesis, 779 (1973). Secondary and tertiary alcohols are converted to alkyl fluorides: Synthesis, 653 (1974). Diazotization of ɑ-amino acids in the presence of the reagent provides good yields of ɑ-fluoro acids: Synthesis, 654 (1974). Reaction with aryldiazonium salts or triazenes leads to aryl fluorides, providing a convenient alternative to the Balz-Schiemann reaction (see Tetrafluoroboric acid, L14037): J. Am. Chem. Soc., 97, 208 (1975); J. Chem. Soc., Chem. Commun., 914 (1979); Bull. Chem. Soc. Jpn., 63, 2058 (1990).
• In combination with nitrosonium tetrafluorborate, ketoximes are converted to gem-difluorides: Synlett, 425 (1994).
• For use in electrophilic electrochemical fluorination, see: J. Fluorine Chem., 83, 31 (1997).
• The reagent is also widely applied to the cleavage of a variety of silyl protecting groups including TBDMS, TES, TBDPS and TIPS: Synthesis, 453 (1986); J. Am .Chem. Soc., 112, 7001 (1990); for further discussion see: P. Kocienski, Protecting Groups, Thieme, Stuttgart (1994).