# BSTFA

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/BSTFA
> Markdown URL: https://mediated.wiki/source/BSTFA.md
> Source: https://en.wikipedia.org/wiki/BSTFA
> Source revision: 1315602751
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 453517835
| Name = BSTFA
| ImageFileL1 = BSTFA-2D-skeletal-abbreviated.png
| ImageAltL1 = Skeletal formula of BSTFA
| ImageSizeL1 = 120
| ImageFileR1 = BSTFA-based-on-similar-xtals-3D-balls.png
| ImageAltR1 = Ball-and-stick model of the BSTFA molecule
| ImageSizeR1 = 120
| IUPACName = trimethylsilyl 2,2,2-trifluoro-''N''-trimethylsilylethanimidate
| OtherNames = BSTFA, ''N'',''O''-Bis(trimethylsilyl)trifluoroacetamide
|Section1={{Chembox Identifiers
| SMILES = C[Si](C)(C)O\C(\C(F)(F)F)=N\[Si](C)(C)C
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 25561-30-2
| PubChem = 94358
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4518443
| ChEBI_Ref = {{ebicite|changed|EBI}} 
| ChEBI = 85067
| InChI = 1/C8H18F3NOSi2/c1-14(2,3)12-7(8(9,10)11)13-15(4,5)6/h1-6H3/b12-7+
| InChIKey = XCOBLONWWXQEBS-KPKJPENVBV
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C8H18F3NOSi2/c1-14(2,3)12-7(8(9,10)11)13-15(4,5)6/h1-6H3/b12-7+
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = XCOBLONWWXQEBS-KPKJPENVSA-N
  }}
|Section2={{Chembox Properties
| C=8 | H=18 | F=3 | N=1 | O=1 | Si=2
| Appearance = colourless liquid
| Density = 0.96
| Solubility = 
| MeltingPtC = -10
| MeltingPt_notes = 
| BoilingPtC = 45-55
| BoilingPt_notes = 14 mm Hg
 }}
}}

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

It is often used to convert [hydroxyl](/source/hydroxyl) groups to [trimethylsilyl ether](/source/Silyl_ether) groups (Me = CH<sub>3</sub>):
:{{chem2| 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](/source/gas_chromatography).<ref>{{cite book |doi=10.1002/047084289X.rn01923 |chapter=N,O-Bis(trimethylsilyl)trifluoroacetamide (BSTFA) |title=Encyclopedia of Reagents for Organic Synthesis |year=2001 |last1=Ito |first1=Katsuji |last2=Nakayama |first2=Yuki |pages=1–4 |isbn=9780470842898 }}</ref>

This reagent was first reported in 1968.<ref>{{cite journal | last1 = Stalling | first1 = DL | last2 = Gehrke | first2 = CW | last3 = Zumwalt | first3 = RW | date = May 1968 | title = A new silylation reagent for amino acids bis(trimethylsilyl)trifluoroacetamide (BSTFA) | url = | journal = Biochemical and Biophysical Research Communications | volume = 31 | issue = 4| pages = 616–22 | pmid = 5656249 }}</ref>

==Related compound==
*[Bis(trimethylsilyl)acetamide](/source/Bis(trimethylsilyl)acetamide), {{chem2|MeC(OSiMe3)NSiMe3}}

==References==
<references/>

Category:Trimethylsilyl compounds

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Adapted from the Wikipedia article [BSTFA](https://en.wikipedia.org/wiki/BSTFA) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/BSTFA?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.