87749-50-6 | Tetrabutylammonium fluoride trihydrate

CAS:87749-50-6 | Tetrabutylammonium fluoride trihydrate ,Description

Tetrabutylammonium fluoride trihydrate, also known as TBAF.H2O, is a salt commonly used in the fields of organic chemistry and biochemistry. It is a strong base and is used in a variety of applications, such as in the synthesis of organic compounds, in the preparation of buffers, and in the purification of proteins.H2O.
 

Scientific Research Applications

Deprotection and Transesterification in Nucleotide Triesters

Tetrabutylammonium fluoride is effective in removing protective groups from nucleotides and exchanging them with other groups, offering a route to various phosphate esters. It's particularly useful in the synthesis of unique nucleotide analogues, although conditions can affect the outcomes (Ogilvie & Beaucage, 1979).

Synthesis of 5-Substituted 1H-Tetrazoles

Acting as a catalyst in the cycloaddition reaction of organic nitriles with trimethylsilyl azide, Tetrabutylammonium fluoride aids in forming 5-substituted 1H-tetrazoles under solventless conditions, providing high yields under mild conditions (Amantini et al., 2004).

Fluoride Source for Silicon-Carbon Bond Cleavage

It serves as a fluoride source for cleaving silicon-carbon bonds, creating carbanions that couple with various electrophiles. It offers advantages over other fluoride sources due to its anhydrous nature, solubility, and lower basicity (Pilcher & DeShong, 1996).

Deprotection of Vinyl Bromides

Tetrabutylammonium fluoride is a mild and efficient base for dehydrobromination of vinyl bromides, converting them to terminal acetylenes with high yield, showing tolerance to water presence (Okutani & Mori, 2007).

Purification of Oligoribonucleotides

It has been used in the purification process of chemically synthesized RNA, improving the synthesis quality and yield, and proving effective in biologically active RNA production (Sproat et al., 1995).

Catalysis in Organic Synthesis

Tetrabutylammonium fluoride is a catalyst for the addition of trialkylsilylalkynes to aldehydes, ketones, and trifluoromethyl ketones, showing good yields and tolerating a variety of aryl functional groups (Chintareddy et al., 2011).

Opening of Epoxides with Thiols

It catalyzes the opening of epoxides with thiols, producing β-hydroxy thioethers with high yields and regioselectivity (Albanese, Landini, & Penso, 1994).

Synthesis of Cellulose Acetate

The solvent dimethyl sulfoxide/tetrabutylammonium fluoride trihydrate is used for acetylation of cellulose, producing cellulose acetate with varying degrees of substitution, impacted by the concentration of Tetrabutylammonium fluoride (Ass, Frollini, & Heinze, 2004).

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