What is TBAF used for?
As a fluoride source in organic solvents, TBAF is used to remove silyl ether protecting groups. It is also used as a phase transfer catalyst and as a mild base.
What is TBAF reagent?
Tetrabutylammonium fluoride (TBAF) can be used as a reagent: For the deprotection of silyl and N-sulfonyl groups. In the fluorination reactions. To synthesize 2-substituted indoles by cyclization reaction of various 2-ethynylanilines with terminal alkynes using Pd catalyst.
Is TBAF an acid?
In contrast to these bases, tetrabutylammonium fluoride (TBAF) is moderately basic, highly soluble in organic solvents, and weakly nucleophilic. Based on these results, TBAF should be considered as the preferred base for (11) C-methylation reactions using 1.
How do I get rid of TBAF?
Having demonstrated that a combination of sulfonic acid resin and calcium carbonate can effectively remove TBAF from THF solution, we then studied the effectiveness of this work-up method of TBAF-promoted TBS-deprotection.
How do you remove Tbaf from a reaction mixture?
Dissolve your mixture in diethylether. TBAF is also soluble in Et2O. Now you can use the fact that TBA-chloride is not soluble in Et2O and wash your mixture several times with NH4Cl. This will remove tetrabutylammonium salts completely for sure.
Is Tbaf water soluble?
Alternate Name: TBAF. Physical Data: TBAF·xH2O: mp 62–63 °C. Solubility: sol H2O, THF, MeCN. Form Supplied in: trihydrate, 1.0 M solution in THF, and 75 wt % solution in water.
Is Tbaf soluble in water?
Tetrabutylammonium fluoride Properties Melting point: 62-63 °C(lit.) Miscible with terahydrofuran, acetonitrile, dimethyl sulfoxide and organic solvents. Insoluble in water.
Is magnesium a fluoride?
Magnesium fluoride is an inorganic compound with the formula MgF2. The compound is a white crystalline salt and is transparent over a wide range of wavelengths, with commercial uses in optics that are also used in space telescopes. It occurs naturally as the rare mineral sellaite.
Is KF a salt?
Potassium fluoride is a fluoride salt having K+ as the counterion. It is a fluoride salt and a potassium salt.
What is the boiling point of THF?
150.8°F (66°C)
Tetrahydrofuran/Boiling point
What makes up magnesium fluoride?
Magnesium fluoride is prepared from magnesium oxide with sources of hydrogen fluoride such as ammonium bifluoride: MgO + (NH4)HF2 → MgF2 + NH3 + H2O. The structure of the compound is similar to that in rutile, featuring octahedral Mg2+ centers and 3-coordinate fluoride centres.
How is the anhydrous fluoride ( TBAF ) prepared?
Instead, anhydrous TBAF has been prepared by the reaction of hexafluorobenzene and tetrabutylammonium cyanide. Solutions of the salt in acetonitrile and dimethyl sulfoxide are stable. Because the fluoride ion is such a strong hydrogen bond acceptor, its salts tend to be hydrated and of limited solubility in organic solvents.
How is tetrabutylammonium bromide ( TBAF ) prepared?
TBAF can be prepared by passing hydrofluoric acid through an ion-exchange resin, followed by tetrabutylammonium bromide. Upon evaporation of the water, TBAF can be collected as an oil in quantitative yield.
How does TBAF work as a deprotecting agent?
As a deprotecting agent, TBAF in DMSO will convert O-silylated enolates into carbonyls. With C-Si bonds, TBAF gives carbanions that can be trapped with electrophiles or undergo protonolysis. ^ a b cLi, Hui-Yin; Sun, Haoran; DiMagno, Stephen G. (2007).
How is the white solid trihydrate TBAF prepared?
It is commercially available as the white solid trihydrate and as a solution in tetrahydrofuran. TBAF is used as a source of fluoride ion in organic solvents. TBAF can be prepared by passing hydrofluoric acid through an ion-exchange resin, followed by tetrabutylammonium bromide.