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TBAF

(Tetra-n-butylammonium Fluoride)









General Information:


Structure:



CAS Number: 87749-50-6 (trihydrate)

Molecular Weight: 261.46 g/mol (anhydrous basis)

    315.51 (trihydrate)


TBAF is a quaternary salt that is used as a source of fluorine. The fluorine anion is typically used for deprotection of silyl ether groups or as a mild base. The good solubility of TBAF in organic solvents makes it a useful alternative to poorly soluble inorganic bases. Reactions involving TBAF are typically carried out at temperatures below 100 C due to its low thermal stability.


TBAF is typically obtained as a trihydrate (TBAF-3H2O), 1M solution in THF, or 75 wt% solution in H2O. TBAF will always contain some water due to the fact that the fluorine ion is such a great hydrogen bond acceptor.




Common Uses:


Reagent for the SEM deprotection





Reagent for TBS deprotection





Reagent in substitution reactions with TMSCN





Reagent in SNAr reactions with TMSCN





Safety:


TBAF is very hygroscopic. Contact of TBAF with acid liberates toxic gas.




References:


1) Patent Reference: WO2015140133, page 103, (11.7 MB)

2) Patent Reference: WO2014152144, page 59, (4.6 MB)

3) Patent Reference: WO2016014463, page 101, (6.7 MB)

4) Patent Reference: WO2016011390, page 151, (20.2 MB)

5) Wikipedia: Tetra-n-butylammonium fluoride (link)

6) www.sigmaaldrich.com: Tetrabutylammonium fluoride solution (link)

7) Pearson, A. J.; Roush, W. R.; Handbook of Reagents for Organic Synthesis, Activating Agents and Protecting Groups