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62778-11-4 - Hydrogen fluoride pyridine complex, ca 70% HF - Olah's Reagent - Pyridinium poly(hydrogen fluoride) - L17117 - Alfa Aesar

L17117 Hydrogen fluoride pyridine complex, ca 70% HF

CAS-Nummer
62778-11-4
Synonyme
Olah's Reagent
Pyridinium poly(hydrogen fluoride)

Größe Preis ($) Menge Verfügbarkeit
25g 37,17
100g 78,30
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Hydrogen fluoride pyridine complex, ca 70% HF

MDL
MFCD00012436

Chemische Eigenschaften

Siedepunkt
50°/1mm
Dichte
1.100
Sensitivität
Moisture Sensitive

Anwendungen

Hydrogen fluoride pyridine complex is used to prepare beta-fluoroamines via reaction with amino alcohols. As a fluorinating agent, is involved in the fluorination of 2,2-diary-1,3-dithiolanes. It is associated with nitrosonium tetrafluorborate to prepare gem-difluorides by reacting with ketoximes. It is also used to convert secondary and tertiary alcohols into their respective alkyl fluorides.

Bemerkungen

Moisture sensitive. Store in cool place. Incompatible with strong bases, alkali metals, strong oxidizing agents, metals and strong acids. It reacts violently with water.

Literaturverweise

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).

Metayer, B.; Compain, G.; Jouvin, K.; Martin-Mingot, A.; Bachmann, C.; Marrot, J.; Thibaudeau, S. Chemo-and Stereoselective Synthesis of Fluorinated Enamides from Ynamides in HF/Pyridine: Second-Generation Approach to Potent Ureas Bioisosteres. J. Org. Chem. 2015, 80 (7), 3397-3410.

Wang, Q.; Zhong, W.; Wei, X.; Ning, M.; Meng, X.; Li, Z. Metal-free intramolecular aminofluorination of alkenes mediated by PhI (OPiv) 2/hydrogen fluoride-pyridine system. Org. Biomol. Chem. 2012, 10 (43), 8566-8569.

GHS Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H300-H310-H330-H314-H318

Fatal if swallowed. Fatal in contact with skin. Fatal if inhaled. Causes severe skin burns and eye damage. Causes serious eye damage.

Sicherheitshinweise: P260-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P361-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Specific treatment is urgent (see label). Rinse mouth. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Weitere Referenzen

Merck
14,6821
Beilstein
4750151
Gefahrenklasse
8
Verpackungsgruppe
I
Harmonized Tariff Code
2933.39
TSCA
No

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