429-41-4 | Tetrabutylammonium fluoride

CAS:429-41-4 | Tetrabutylammonium fluoride ,Description

Tetrabutylammonium fluoride (TBAF) is an organofluoride compound used in organic syntheses and in analytical chemistry. It is a colorless, hygroscopic, and water-soluble solid. TBAF is a highly versatile compound, with a wide range of applications in organic synthesis, analytical chemistry, and biochemistry. It is used as a reagent for the deprotection of protected alcohols, for the synthesis of fluorinated compounds, and for the analysis of biomolecules.
 

Scientific Research Applications

• Fluoride Recognition and Bihalide Ion Interaction: TBAF is utilized in studying fluoride recognition by molecular receptors and its interaction with bihalide ions (Goursaud et al., 2012).
• Deprotection and Transesterification in Nucleotides: It is effective for removing various protective groups from nucleotides, facilitating the synthesis of diverse phosphate esters and novel nucleotide analogs (Ogilvie & Beaucage, 1979).
• Catalysis in Organic Synthesis: TBAF acts as a mild and efficient catalyst for synthesizing 3,5-disubstituted-1,2,4-oxadiazoles (Gangloff et al., 2001) and in the regioselective opening of epoxides with thiols (Albanese et al., 1994).
• Base for Chemical Reactions: It serves as a mild and efficient base for dehydrobromination reactions and in generating products from methyl propiolate and carbonyl derivatives (Okutani & Mori, 2007), (Tejedor et al., 2010) .
• Fluorination in Peptides and Drugs: TBAF aids in the rapid introduction of fluorine into peptides and functionalized drugs (Jacobson et al., 1988).
• Synthesis of Functionalized Compounds: It is an effective organocatalyst for synthesizing multifunctionalized cyclopentenes and for nucleophilic aromatic fluorinations (Alishetty et al., 2018), (Hu et al., 2010).
• Fluoride Source in Sensor Development: It is commonly used for developing fluoride sensors (Brettell-Adams et al., 2018).
• Catalyst in Synthesis Procedures: TBAF catalyzes the synthesis of various compounds such as CF(3)-bearing tertiary propargylic alcohols and 5-substituted 1H-tetrazoles (Chintareddy et al., 2011), (Amantini et al., 2004).
• Stability and Synthetic Utility: TBAF is noted for its stability and utility in synthetic procedures, including Hofmann elimination and desilylation processes (Sun & DiMagno, 2005).

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