245585

Sigma-Aldrich

Sodium bis(trimethylsilyl)amide solution

1.0 M in THF

Synonym(s):
Hexamethyldisilazane sodium salt solution
Linear Formula:
[(CH3)3Si]2NNa
CAS Number:
Molecular Weight:
183.37
Beilstein/REAXYS Number:
3629917
MDL number:
PubChem Substance ID:

Quality Level

concentration

1.0 M in THF

density

0.904 g/mL at 25 °C

SMILES string

C[Si](C)(C)N([Na])[Si](C)(C)C

InChI

1S/C6H18NSi2.Na/c1-8(2,3)7-9(4,5)6;/h1-6H3;/q-1;+1

InChI key

WRIKHQLVHPKCJU-UHFFFAOYSA-N

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General description

Sodium bis(trimethylsilyl)amide solution (NaHMDS) is widely used as a strong base in organic synthesis for deprotonation reactions and base-catalyzed reactions. It is also involved in the generation of enolates, Wittig reagents and carbenes.

Application

NaHMDS can be used as a base:
  • In the synthesis of N-boc-1-amino-1,3-diene derivatives from N-boc-1-amino-4-methoxy-2-alkenes via 1,4-elimination reactions.
  • To deprotonate alkyl or aryl ketones to generate enolate derivatives by hydroxylation reaction.
  • In the enantioselective synthesis of 1,2-amino alcohols by the reaction between various nitroalkanes and aldehydes via nitroaldol reaction promoted by bimetallic heterogeneous catalyst.

Packaging

18, 20 L in steel drum
4×25, 100, 4×100, 800 mL in Sure/Seal™
The 25 mL Sure/Seal bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.

Legal Information

Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

Signal Word

Danger

Supp Hazards

EUH014 - EUH018 - EUH019

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 2924 8(3) / PGII

WGK Germany

WGK 2

Flash Point(F)

1.4 °F - closed cup

Flash Point(C)

-17 °C - closed cup

Certificate of Analysis

Certificate of Origin

Stereoselective preparation of (1Z)-and (1E)-N-Boc-1-amino-1, 3-dienes by stereospecific base-promoted 1, 4-elimination
Tayama E and Toma Y
Tetrahedron, 71(4), 554-559 (2015)
Lithium and potassium bis (trimethylsilyl) amide: Utilizing non-nucleophilic bases as nitrogen sources
Bruning J, et al.
Tetrahedron Letters, 38(18), 3187-3188 (1997)
Macromolecules, 39, 5347-5347 (2006)
Xiaoguang Li et al.
Chemical communications (Cambridge, England), 47(38), 10761-10763 (2011-08-30)
A silica microsphere suspension and a silica sol are employed in a two-step dipping process for the preparation of a superhydrophobic surface. It's not only a facile way to achieve the lotus effect, but can also create a multi-functional surface...
Tatsuya Nitabaru et al.
Journal of the American Chemical Society, 131(38), 13860-13869 (2009-09-10)
Full details of an anti-selective catalytic asymmetric nitroaldol reaction promoted by a heterobimetallic catalyst comprised of Nd(5)O(O(i)Pr)(13), an amide-based ligand, and NaHMDS (sodium hexamethyldisilazide) are described. A systematic synthesis and evaluation of amide-based ligands led to the identification of optimum...

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