| Customization: | Available |
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| CAS No.: | 87749-50-6 |
| Formula: | C16h38fno |
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| Product names | Tetra-n-butylammonium fluoride trihydrate;(TBAF) |
| CAS No | 87749-50-6 |
Chemical Properties
Tetra-n-butylammonium fluoride trihydrate (TBAF) is a quaternary ammonium salt. It is a white crystalline solid or crystalline powder, with a molecular mass of 279.48 g/mol. TBAF is highly soluble in water and has a melting point of 62-63°C. It is hygroscopic and sensitive to moisture.
Preparation
TBAF can be prepared by passing hydrofluoric acid through an ion-exchange resin, followed by reaction with tetrabutylammonium bromide. The trihydrate form is commonly used due to its stability and ease of handling. Anhydrous TBAF can also be prepared by reacting hexafluorobenzene with tetrabutylammonium cyanide.
Applications
Deprotection Agent: TBAF is widely used to remove silyl ether protecting groups in organic synthesis. It is effective in cleaving silicon-oxygen bonds and is often used in the deprotection of silyl-protected alcohols and amines.
Phase Transfer Catalyst: TBAF acts as a phase-transfer catalyst in reactions involving organic and aqueous phases, facilitating the transfer of reactants between phases.
Mild Base: TBAF is used as a mild base in various organic reactions, including aldol-type condensation reactions, Michael-type reactions, and ring-opening reactions.
Fluorination and Desulfonylation: TBAF is used in fluorination reactions and as a reagent for desulfonylation.
Synthesis of Pharmaceuticals: TBAF is an important intermediate in the synthesis of pharmaceuticals, such as 6-fluoropurine and its derivatives.
Storage and Handling
TBAF should be stored below 30°C and protected from moisture due to its hygroscopic nature. It is recommended to dry TBAF before use to ensure optimal performance in reactions.
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