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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

Número CAS
62778-11-4
Nombre Alternativo
Olah's Reagent
Pyridinium poly(hydrogen fluoride)

Tamaño Precio ($) Cantidad Disponibilidad
25g 37,17
100g 78,30
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Hydrogen fluoride pyridine complex, ca 70% HF

MDL
MFCD00012436

Propiedades químicas

Punto de ebullición
50°/1mm
Densidad
1.100
Sensibilidad
Moisture Sensitive

Aplicaciones

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.

Notas

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

Referencias documentales

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.

Indicaciones de peligro y de precaución del GHS

Indicaciones de peligro (UE): 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.

Indicaciones de precaución: 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.

Otras referencias

Merck
14,6821
Beilstein
4750151
Clase de peligro
8
Grupo de embalaje
I
Código de tarifa arancelaria unificado
2933.39
TSCA
No

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