Hydrogen fluoride pyridine complex

• Catalog No.: L17117
• CAS Number: 62778-11-4
• M. F.: C5H6FN
• M. W.: 99.1062432
• Purity: ca 70% HF

SYNONYMS

• Title: 氟化氢吡啶络合物
• IUPAC name: pyridine hydrofluoride
• IUPAC Traditional name: pyridine hydrofluoride
• Synonyms: Pyridinium poly(hydrogen fluoride); Olah's Reagent

DATABASE IDS

• MDL Number: MFCD00012436
• Merck Index: 146821
• Beilstein Number: 4750151
• CAS Number: 62778-11-4

PROPERTIES

• Purity: ca 70% HF
• Boiling Point: 50°C/1mm
• Density: 1.100
• GHS Hazard statements: H300-H310-H330-H314-H318
• European Hazard Symbols: Highly toxic (T+)
• GHS Precautionary statements: P260-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P361-P405-P501A
• Risk Statements: 26/27/28-35
• Safety Statements: 26-28-36/37/39-45
• Storage Warning: Moisture Sensitive
• TSCA Listed: 否
• Hazard Class: 8
• UN Number: UN1790
• Packing Group: I

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).