BSTFA

Chemical compound

N,O-Bis(trimethylsilyl)trifluoroacetamide (BSTFA) is an organosilicon compound. It is a colorless liquid that is very sensitive to traces of water or alcohols.

It is often used to convert hydroxyl groups to trimethylsilyl ether groups (Me = CH₃):

ROH + CF₃C(OSiMe₃)NSiMe₃ → CF₃C(O)NH(SiMe₃) + ROSiMe₃

These silylated derivatives are amenable to analysis or further manipulation. Siloxanes are invariably more volatile than their hydroxyl precursors, and thus they can be more easily analyzed with gas chromatography.^[1]

This reagent was first reported in 1968.^[2]

Related compound

• Bis(trimethylsilyl)acetamide, MeC(OSiMe₃)NSiMe₃

References

1. Ito, Katsuji; Nakayama, Yuki (2001). "N,O-Bis(trimethylsilyl)trifluoroacetamide (BSTFA)". Encyclopedia of Reagents for Organic Synthesis. pp. 1–4. doi:10.1002/047084289X.rn01923. ISBN 9780470842898.
2. Stalling DL, Gehrke CW, Zumwalt RW. A new silylation reagent for amino acids bis(trimethylsilyl)trifluoroacetamide (BSTFA). Biochemical and Biophysical Research Communications. 1968 May 23;31(4):616-22. PMID 5656249