BSTFA

BSTFA  | Skeletal formula of BSTFA | Ball-and-stick model of the BSTFA molecule

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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

PubChem CID

* 94358

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

Tracking categories (test):

* PairSizeSet

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 + CF
3C(OSiMe
3)NSiMe
3 → CF
3C(O)NH(SiMe
3) + ROSiMe

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(OSiMe
3)NSiMe

## 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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*[CID]: Compound ID