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Merck
CN

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

Key Documents

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Product Name

Sodium bis(trimethylsilyl)amide solution, 1.0 M in THF

InChI

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

SMILES string

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

InChI key

WRIKHQLVHPKCJU-UHFFFAOYSA-N

form

liquid

concentration

1.0 M in THF

density

0.904 g/mL at 25 °C

Quality Level

200

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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.

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.

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

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

EUH014,EUH019

Storage Class

3 - Flammable liquids

wgk

WGK 2

flash_point_f

1.4 °F - closed cup

flash_point_c

-17 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
SDBB3872
SHBS6834
STBL0251
STBK0566
STBJ3578

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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)
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)
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)
Elsa Vennat et al.
Dental materials : official publication of the Academy of Dental Materials, 25(6), 729-735 (2009-01-29)
The objectives of this study were to assess demineralized dentin porosity and quantify the different porous features distribution within the material using mercury intrusion porosimetry (MIP) technique. We compared hexamethyldisilazane (HMDS) drying and lyophilization (LYO) (freeze-drying) in sample preparation. Fifty-six
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