What is Tetrabutylammonium fluoride?

Identification

Product Name:    Tetrabutylammonium fluoride

CAS:    429-41-4    

MF:    C16H36FN    

MW:    261.46    

EINECS:    207-057-2

Molecular Structure 

Properties

Melting point     62-63 °C(lit.)   

density     0.953 g/mL at 25 °C   

refractive index     n20/D 1.456   

Fp     1 °F   

storage temp.     2-8°C   

solubility     Miscible with terahydrofuran, acetonitrile, dimethyl sulfoxide and organic solvents.    

form     Solution    

color     Clear light greenish to brown    

Water Solubility     Insoluble in water.    

Tetrabutylammonium fluoride hydrate is known to be a source of F− anion, used in nucleophilic fluorination reactions. It can be made anhydrous typically by heating it around 40 °C under vacuum.

Application

Tetrabutylammonium fluoride is a reagent in organic syntheses in addition, condensation, base-catalyzed cyclization reactions, fluorination and desulfonylation reactions and as a deprotecting agent. Typically dried prior to use. It is a catalyst for etherification of alcohols and phenols with alkyl halides Catalyst for benzylation reactions.

Tetrabutylammonium Fluoride is a reactant used for the synthesis of multiple compounds, including conjugated dienoic acid esters, oligoribonucleotides with phosphonate-modified linkages, and triple monoamine reuptake inhibitors, among others. It has proven useful in studying cancer, diabetes, and neurochemistry.

It is the reactant for preparation of:

• Double clathrate hydrates at high pressures

• Cellulose ethers

• Terminal olefins via dehydrohalogenation reactions

• Neutral and zwitterionic 3-carboranyl thymidine analogues for boron neutron capture therapy

Tetrabutylammonium fluoride hydrate can be used:

• To prepare 2,7-diethynyl-9-propyl-9H-carbazole, which is a key intermediate for the synthesis of calix[4]arene−carbazole polymers.

• As an anion source in the study of selective detection of F− by anion receptor viz Schiff base.

• To prepare terminal olefins from primary alkyl iodides.