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245585

Sigma-Aldrich

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:
1070-89-9
Molecular Weight:
183.37
Beilstein:
3629917
MDL number:
MFCD00009835
UNSPSC Code:
12352111
PubChem Substance ID:
24854742
NACRES:
NA.22

form

liquid

Quality Level

200

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

H225,H314,H335,H336,H351

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

EUH014,EUH019

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Macromolecules, 39, 5347-5347 (2006)
Xiaoguang Li et al.
Chemical communications (Cambridge, England), 47(38), 10761-10763 (2011-08-30)
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