Bis(trimethylsilyl)acetamide

Bis(trimethylsilyl)acetamide
Names
Preferred IUPAC name
N-Trimethylsilyl-1-trimethylsilyloxyethanimine
Systematic IUPAC name
Trimethylsilyl N-(trimethylsilyl)ethanecarboximidate
Other names
N,O-Bis(trimethylsilyl)acetamide
Identifiers
10416-59-8 (E), chlorotimethylsilane
101660-04-2
Abbreviations BSA
1306669
ChemSpider 23581 YesY
4523073 (E) YesY
10516629 (Z) YesY
EC Number 233-892-7
Jmol interactive 3D Image
Image
MeSH N,O-bis(trimethylsilyl)acetamide
PubChem 25248
6913588 (E)
5372922 (Z)
RTECS number AK3000000
UN number 2920
Properties
C8H21NOSi2
Molar mass 203.43 g·mol−1
Appearance Liquid
Density 0.832 g cm−3
Boiling point 71 to 73 °C (160 to 163 °F; 344 to 346 K) at 35mmHg
Hazards
Corrosive (C)
R-phrases R10 R14 R22 R34
S-phrases S26 S36/37/39 S45
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).
Infobox references

Bis(trimethylsilyl)acetamide (BSA) is an organosilicon compound with the formula Me3SiNC(OSiMe3)Me (Me = CH3). It is a colorless liquid that is soluble in diverse organic solvents, but reacts rapidly with compounds, including solvents and moisture, containing OH and NH functional groups. It is used in analytical chemistry for the derivatisation of compounds in analysis to increase their volatility, e.g. for gas chromatography.[1] It is also used to introduce the 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:[2]

2 Me3SiCl + H2NC(O)Me + 2 Et3N → Me3SiNC(OSiMe3)Me + 2 Et3NHCl

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

ROH + Me3SiNC(OSiMe3)Me → Me3SiN(H)C(O)Me + 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. 1 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.
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