Bis(trimethylsilyl)acetamide

{{short description|Chemical compound}}

{{Chembox

| Name =

| ImageFile =

| ImageFile1 = Bis(trimethylsilyl)acetamide.svg

| ImageName1 = Structural formula of (E)-bis(trimethylsilyl)acetamide

| ImageFile2 = Bis(trimethylsilyl)acetamide-3D.png

| ImageName2 = Ball and stick model of (E)-bis(trimethylsilyl)acetamide

| PIN = Trimethylsilyl N-(trimethylsilyl)ethanecarboximidate

| OtherNames = N,O-Bis(trimethylsilyl)acetamide

| IUPACName =

| Section1 = {{Chembox Identifiers

| Abbreviations = BSA

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 10416-59-8

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = R14N49I64O

| PubChem = 25248

| PubChem1 = 6913588

| PubChem1_Comment = (E)

| PubChem2 = 5372922

| PubChem2_Comment = (Z)

| ChemSpiderID = 23581

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID1 = 4523073

| ChemSpiderID1_Comment = (E)

| ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID2 = 10516629

| ChemSpiderID2_Comment = (Z)

| ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}}

| EINECS = 233-892-7

| UNNumber = 2920

| MeSHName = N,O-bis(trimethylsilyl)acetamide

| RTECS = AK3000000

| SMILES = CC(=N[Si](C)(C)C)O[Si](C)(C)C

| SMILES1 = CC(O[Si](C)(C)C)=N[Si](C)(C)C

| StdInChI = 1S/C8H21NOSi2/c1-8(9-11(2,3)4)10-12(5,6)7/h1-7H3

| InChI = 1/C8H21NOSi2/c1-8(9-11(2,3)4)10-12(5,6)7/h1-7H3/b9-8+

| StdInChIKey = SIOVKLKJSOKLIF-UHFFFAOYSA-N

| Beilstein = 1306669

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| Section2 = {{Chembox Properties

| C=8 | H=21 | N=1 | O=1 | Si=2

| Appearance = Liquid

| Density = 0.832 g cm⁻³

| BoilingPtC = 71 to 73

| BoilingPt_notes = at 35mmHg

| MeltingPtC = 24

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| Section3 =

| Section4 =

| Section5 =

| Section6 =

| Section7 = {{Chembox Hazards

| GHSPictograms = {{GHS02}}{{GHS05}}{{GHS07}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|226|302|314}}

| PPhrases = {{P-phrases|210|233|240|241|242|243|260|264|270|280|301+312|301+330+331|303+361+353|304+340|305+351+338|310|321|330|363|370+378|403+235|405|501}}

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| Section8 = {{Chembox Related

| OtherFunction_label = Amides

| OtherFunction = Dimethylacetamide

}}

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Bis(trimethylsilyl)acetamide (BSA) is an organosilicon compound with the formula {{chem2|MeC(OSiMe3)NSiMe3 }} (Me = CH₃). It is a colorless liquid that is soluble in diverse organic solvents, but reacts rapidly with moisture and solvents containing OH and NH groups. It is used in analytical chemistry to increase the volatility of analytes, e.g., for gas chromatography.{{cite book |title=Handbook of Derivatives for Chromatography |edition=2nd|last=Blau |first=Karl |author2=J. M. Halket |year=1993 |publisher=John Wiley & Sons |isbn= 0-471-92699-X |url=http://eu.wiley.com/WileyCDA/WileyTitle/productCd-047192699X.html }} It is also used to introduce the trimethylsilyl protecting group in organic synthesis.Harry Heaney, Jian Cui, “N,O-Bis(trimethylsilyl)acetamide” Encyclopedia of Reagents for Organic Synthesis Copyright © 2007 John Wiley & Sons. {{doi|10.1002/047084289X.rb208.pub2}}. A related reagent is N,O-bis(trimethylsilyl)trifluoroacetamide (BSTFA).