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
UNSPSC Code:
12352111
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
3629917
Concentration:
1.0 M in THF
Form:
liquid
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
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
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Danger
hcodes
Hazard Classifications
Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3
target_organs
Central nervous system, Respiratory system
supp_hazards
Storage Class
3 - Flammable liquids
flash_point_f
1.4 °F - closed cup
flash_point_c
-17 °C - closed cup
ppe
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
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Synthetic studies on (1S)-1-(6, 7-dimethoxy-2-naphthyl)-1-(1H-imidazol-4-yl)-2-methylpropan-1-ol as a selective C17, 20-lyase inhibitor
Matsunaga N, et al.
Tetrahedron Asymmetry, 15(13), 2021-2028 (2004)
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)