• Source: Bis(trimethylsilyl)acetamide

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

Kata Kunci Pencarian:

• Bis(trimethylsilyl)acetamide
• Trimethylsilyl group
• Silylation
• BSA
• BSTFA
• Cangrelor
• Diacetylene
• List of organic salts
• Nitrile
• Hydrogen peroxide