Bis(trimethylsilyl)acetamide

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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
3D model (
JSmol
)
Abbreviations BSA
1306669
ChemSpider
ECHA InfoCard
100.030.799 Edit this at Wikidata
EC Number
  • 233-892-7
MeSH N,O-bis(trimethylsilyl)acetamide
RTECS number
  • AK3000000
UNII
UN number 2920
  • InChI=1S/C8H21NOSi2/c1-8(9-11(2,3)4)10-12(5,6)7/h1-7H3
    Key: SIOVKLKJSOKLIF-UHFFFAOYSA-N
  • InChI=1/C8H21NOSi2/c1-8(9-11(2,3)4)10-12(5,6)7/h1-7H3/b9-8+
  • CC(=N[Si](C)(C)C)O[Si](C)(C)C
  • CC(O[Si](C)(C)C)=N[Si](C)(C)C
Properties
C8H21NOSi2
Molar mass 203.432 g·mol−1
Appearance Liquid
Density 0.832 g cm−3
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:
GHS02: FlammableGHS05: CorrosiveGHS07: Exclamation mark
Danger
H226, H302, H314
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 [77 °F], 100 kPa).

Bis(trimethylsilyl)acetamide (BSA) is an

(BSTFA).

Synthesis and reactions

BSA is prepared by treating acetamide with trimethylsilyl chloride in the presence of a base (Me = CH3, Et = C2H5):[2]

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):[3]

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

References