147227-26-7

Basic information

• Product Name: ALPHA,ALPHA-BIS(TRIMETHYLSILYL)-TERT-BUTYLKETIMINE
• Synonyms: ALPHA,ALPHA-BIS(TRIMETHYLSILYL)-TERT-BUTYLKETIMINE;α,α-Bis(trimethylsilyl)-tert-butylketimine
• CAS NO: 147227-26-7
• Molecular Formula: C12H29NSi2
• Molecular Weight: 243.54
• Mol File: 147227-26-7.mol

Chemical Properties

• Boiling Point: 104 °C (8 mmHg)
• Appearance: /
• Refractive Index: 1.4505-1.4525
• Storage Temp.: 0-6°C
• CAS DataBase Reference: ALPHA,ALPHA-BIS(TRIMETHYLSILYL)-TERT-BUTYLKETIMINE(CAS DataBase Reference)
• NIST Chemistry Reference: ALPHA,ALPHA-BIS(TRIMETHYLSILYL)-TERT-BUTYLKETIMINE(147227-26-7)
• EPA Substance Registry System: ALPHA,ALPHA-BIS(TRIMETHYLSILYL)-TERT-BUTYLKETIMINE(147227-26-7)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 147227-26-7(Hazardous Substances Data)

Usage

Chemical Properties

clear yellow liquid

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 66548-20-7 N-(1-Methylethyliden)-tert-butylamin 

Downstream Products

• 937-53-1 (Z)-4-phenylbut-3-en-2-one 
• 1896-62-4 (E)-benzalacetone 

Relevant articles and documents

A convenient route to (E)-α,β-unsaturated methyl ketones

Aldehydes are converted into (E)-α,β-unsaturated methyl ketones in good yield and with a high E stereoselectivity using α,α- bis(trimethylsilyl) N-tert-butyl acetimine 3. The reaction was mediated by a catalytic amount of tetrabutylammonium fluoride (TBAF) under mild conditions. The disilylated reagent 3 is easily generated from N-tert-butylacetimine, lithium diisopropylamide (LDA), and chlorotrimethylsilane. The mechanism of the reaction is discussed. Copyright

A Simple and Highly Stereoselective Route to E-α,β-Unsaturated Aldehydes

Zinc bromide mediated reaction of α,α-bis(trimethylsilyl)-tert-butylacetaldimine (3) with a wide range of aldehydes takes place under mild conditions and affords the corresponding α,β-unsaturated aldehydes in good yields and with high E stereoselectivity (>98percent).This procedure is successfully applied to the preparation of intermediates for retinoid and natural product synthesis.