BSTFA

BSTFA
source ↗	source ↗
Names
	IUPAC name trimethylsilyl 2,2,2-trifluoro-N-trimethylsilylethanimidate
	Other names BSTFA, N,O-Bis(trimethylsilyl)trifluoroacetamide
Identifiers
CAS Number	25561-30-2 Y;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:85067 N;
ChemSpider	4518443 Y;
ECHA InfoCard	100.042.807
PubChem CID	94358;
CompTox Dashboard (EPA)	DTXSID001015789 ;
	InChI InChI=1S/C8H18F3NOSi2/c1-14(2,3)12-7(8(9,10)11)13-15(4,5)6/h1-6H3/b12-7+ Y Key: XCOBLONWWXQEBS-KPKJPENVSA-N Y; 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;
	SMILES C[Si](C)(C)O\C(\C(F)(F)F)=N\[Si](C)(C)C;
Properties
Chemical formula	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). N verify (what is YN ?) Infobox references

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

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.
Stalling, DL; Gehrke, CW; Zumwalt, RW (May 1968). "A new silylation reagent for amino acids bis(trimethylsilyl)trifluoroacetamide (BSTFA)". Biochemical and Biophysical Research Communications. 31 (4): 616–22. PMID 5656249.

[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 (May 1968). "A new silylation reagent for amino acids bis(trimethylsilyl)trifluoroacetamide (BSTFA)". Biochemical and Biophysical Research Communications. 31 (4): 616–22. PMID 5656249.

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