Bis(trimethylsilyl)acetamide
Appearance
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Names | |
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Preferred IUPAC name
Trimethylsilyl N-(trimethylsilyl)ethanecarboximidate | |
Other names
N,O-Bis(trimethylsilyl)acetamide
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Identifiers | |
3D model (
JSmol ) |
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Abbreviations | BSA |
1306669 | |
ChemSpider | |
ECHA InfoCard
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100.030.799 |
EC Number |
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MeSH | N,O-bis(trimethylsilyl)acetamide |
PubChem CID
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RTECS number
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UNII | |
UN number | 2920 |
CompTox Dashboard (EPA)
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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: | |
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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
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Dimethylacetamide |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Bis(trimethylsilyl)acetamide (BSA) is an
trimethylsilyl protecting group in organic synthesis.[2] 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):[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
- ISBN 0-471-92699-X.
- ^ .
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