NaHMDS

[Sodium Bis(trimethylsilyl)amide]

Other Names:

Sodiobis(trimethylsilyl)amine

Sodium hexamethyldisilazane

Sodium hexamethyldisilazide

Hexamethyldisilazane sodium salt solution

General Information:

Structure:

CAS Number: 1070-89-9

Molecular Weight: 183.37 g/mol

Appearance: Off-white solid

Melting Point: 171-175 C

Sodium bis(trimethylsilyl)amide (NaHMDS) is a strong base. It is commercially available as a solid and as a solution in a variety of solvents (ex. THF, toluene, and MTBE). Similar reagents include lithium bis(trimethylsilyl)amide (LiHMDS) and potassium bis(trimethylsilyl)amide (KHMDS).

Common Uses:

Strong base for deprotonations

Procedure excerpt:

To a solution of the indole (0.300 g, 0.92 mmol) in THF (30 mL) was added NaHMDS (1 M in THF, 0.93 mL, 0.93 mmol) at -78 C. The mixture was stirred at -78 C for . . .

[full procedure]

References:

1) Patent Reference: WO2014149164, page 229, (23.7 MB)

2) Wikipedia: Sodium bis(trimethylsilyl)amide (link)

3) www.sigmaaldrich.com: Sodium bis(trimethylsilyl)amide solution (link)

4) www.alfa.com: 33505 Sodium bis(trimethylsilyl)amide, 98% (link)

5) Reich, H. J.; Rigby, J. H.; Handbook of Reagents for Organic Synthesis, Acidic and Basic Reagents