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Bis(trimethylsilyl)acetamide

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Chemical compound
Bis(trimethylsilyl)acetamide
Structural formula of (E)-bis(trimethylsilyl)acetamide
Ball and stick model of (E)-bis(trimethylsilyl)acetamide
Names
Preferred IUPAC name Trimethylsilyl N-(trimethylsilyl)ethanecarboximidate
Other names N,O-Bis(trimethylsilyl)acetamide
Identifiers
CAS Number
3D model (JSmol)
Abbreviations BSA
Beilstein Reference 1306669
ChemSpider
ECHA InfoCard 100.030.799 Edit this at Wikidata
EC Number
  • 233-892-7
MeSH N,O-bis(trimethylsilyl)acetamide
PubChem CID
RTECS number
  • AK3000000
UNII
UN number 2920
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H21NOSi2/c1-8(9-11(2,3)4)10-12(5,6)7/h1-7H3Key: SIOVKLKJSOKLIF-UHFFFAOYSA-N
  • InChI=1/C8H21NOSi2/c1-8(9-11(2,3)4)10-12(5,6)7/h1-7H3/b9-8+
SMILES
  • CC(=N(C)(C)C)O(C)(C)C
  • CC(O(C)(C)C)=N(C)(C)C
Properties
Chemical formula C8H21NOSi2
Molar mass 203.432 g·mol
Appearance Liquid
Density 0.832 g cm
Melting point 24 °C (75 °F; 297 K)
Boiling point 71 to 73 °C (160 to 163 °F; 344 to 346 K) at 35mmHg
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS05: CorrosiveGHS07: Exclamation mark
Signal word Danger
Hazard statements H226, H302, H314
Precautionary statements P210, P233, P240, P241, P242, P243, P260, P264, P270, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P363, P370+P378, P403+P235, P405, P501
Related compounds
Related Amides Dimethylacetamide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Bis(trimethylsilyl)acetamide (BSA) is an organosilicon compound with the formula 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. It is also used to introduce the trimethylsilyl protecting group in organic synthesis. A related reagent is N,O-bis(trimethylsilyl)trifluoroacetamide (BSTFA).

Synthesis and reactions

BSA is prepared by treating acetamide with trimethylsilyl chloride in the presence of a base (Me = CH3, Et = C2H5):

MeC(O)NH2 + 2 SiMe3Cl + 2 Et3N→ MeC(OSiMe3)NSiMe3 + 2 Et3NHCl

The reaction of BSA with alcohols gives the corresponding trimethylsilyl ether, together with acetamide as a byproduct (Me = CH3):

2 ROH + MeC(OSiMe3)NSiMe3 → MeC(O)NH2 + 2 ROSiMe3

References

  1. Blau, Karl; J. M. Halket (1993). Handbook of Derivatives for Chromatography (2nd ed.). John Wiley & Sons. ISBN 0-471-92699-X.
  2. ^ 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.
  3. Young, Steven D.; Buse, Charles T.; Heathcock, Clayton H. (1985). "2-Methyl-2-(Trimethylsiloxy)pentan-3-one". Organic Syntheses. 63: 79. doi:10.15227/orgsyn.063.0079.
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