245585
Sodium bis(trimethylsilyl)amide solution
1.0 M in THF
Synonym(s):
Hexamethyldisilazane sodium salt solution
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About This Item
Linear Formula:
[(CH3)3Si]2NNa
CAS Number:
Molecular Weight:
183.37
Beilstein:
3629917
MDL number:
UNSPSC Code:
12352111
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
form
liquid
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
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
Hazard Statements
Precautionary Statements
Hazard Classifications
Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3
Target Organs
Central nervous system, Respiratory system
Supplementary Hazards
Storage Class Code
3 - Flammable liquids
WGK
WGK 2
Flash Point(F)
1.4 °F - closed cup
Flash Point(C)
-17 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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)
Macromolecules, 39, 5347-5347 (2006)
Lithium and potassium bis (trimethylsilyl) amide: Utilizing non-nucleophilic bases as nitrogen sources
Bruning J, et al.
Tetrahedron Letters, 38(18), 3187-3188 (1997)
Nan Li et al.
Lab on a chip, 8(12), 2105-2112 (2008-11-22)
High-density live cell array serves as a valuable tool for the development of high-throughput immunophenotyping systems and cell-based biosensors. In this paper, we have, for the first time, demonstrated a simple fabrication process to form the hexamethyldisilazane (HMDS) and poly(ethylene
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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