:BSTFA

{{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. 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):

:{{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.{{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 }}

This reagent was first reported in 1968.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}}