BSTFA

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.

BSTFA
Skeletal formula of BSTFA
Ball-and-stick model of the BSTFA molecule
Names
IUPAC name
trimethylsilyl 2,2,2-trifluoro-N-trimethylsilylethanimidate
Other names
BSTFA, N,O-Bis(trimethylsilyl)trifluoroacetamide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.042.807
  • InChI=1S/C8H18F3NOSi2/c1-14(2,3)12-7(8(9,10)11)13-15(4,5)6/h1-6H3/b12-7+ checkY
    Key: XCOBLONWWXQEBS-KPKJPENVSA-N checkY
  • InChI=1/C8H18F3NOSi2/c1-14(2,3)12-7(8(9,10)11)13-15(4,5)6/h1-6H3/b12-7+
    Key: XCOBLONWWXQEBS-KPKJPENVBV
  • C[Si](C)(C)O\C(\C(F)(F)F)=N\[Si](C)(C)C
Properties
C8H18F3NOSi2
Molar mass 257.403 g·mol−1
Appearance colourless liquid
Density 0.96
Melting point −10 °C (14 °F; 263 K)
Boiling point 45–55 °C (113–131 °F; 318–328 K) 14 mm Hg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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]

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
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