Tetra-n-butylammonium fluoride



Tetra-n-butylammonium fluoride
Systematic name Tetra-n-butylammonium fluoride
Chemical formula (C4H9)4NF
Molecular mass 261.46 g/mol
Melting point 58-60 °C (trihydrate)
CAS number [429-41-4] (anhydrous)
[87749-50-6] (trihydrate)
SMILES CCCC[N+](CCCC)(CCCC)CCCC.[F-]
Disclaimer and references

Tetra-n-butylammonium fluoride or TBAF is a quaternary ammonium salt with the chemical formula (CH3CH2CH2CH2)4N+F-. It is commercially available as the trihydrate and as a solution in tetrahydrofuran.

In the laboratory the compound is usually encountered in the latter form as a source of organic-soluble base.

As fluoride is such a strong elimination.[3]

References

  1. ^ Ramesh K. Sharma, James L. Fry (1983). "Instability of anhydrous tetra-n-alkylammonium fluorides". Journal of Organic Chemistry 48: 2112-4. doi:10.1021/jo00160a041.
  2. ^ D. Phillip Cox, Jacek Terpinski, Witold Lawrynowicz (1984). "'Anhydrous' tetrabutylammonium fluoride: a mild but highly efficient source of nucleophilic fluoride ion". Journal of Organic Chemistry 49: 3216-9. doi:10.1021/jo00191a035.
  3. ^ Haoran Sun and Stephen G. DiMagno (2005). "Anhydrous Tetrabutylammonium Fluoride". Journal of the American Chemical Society 127: 2050-1. doi:10.1021/ja0440497.
 
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