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/REAXYS Number: 3629917
• MDL number: MFCD00009835
• PubChem Substance ID: 24854742

Properties

• 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

18, 20 L in steel drum

4×25, 100, 4×100, 800 mL in Sure/Seal™

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,GHS05,GHS07,GHS08
• Signal Word: Danger
• Hazard Statements: H225 - H314 - H335 - H336 - H351
• Precautionary Statements: P201 - P210 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• Supp Hazards: EUH014 - EUH018 - EUH019
• Personal Protective Equipment: dust mask type N95 (US),Eyeshields,Gloves
• RIDADR: UN 2924 8(3) / PGII
• WGK Germany: WGK 2
• Flash Point(F): 1.4 °F - closed cup
• Flash Point(C): -17 °C - closed cup