245585

Sodium bis(trimethylsilyl)amide solution

1.0 M in THF

• Synonym(s): Hexamethyldisilazane sodium salt solution
• 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

Properties

• 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

Description

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

Safety Information

• Pictograms: GHS02,GHS08,GHS05,GHS07
• Signal Word: Danger
• Hazard Statements: H225,H314,H335,H336,H351
• Precautionary Statements: P202 - P210 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• 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