90524-35-9

Basic information

• Product Name: C₁₅H₂₈NOSi⁽¹⁺⁾*CF₃O₃S^(1-)
• Synonyms: C₁₅H₂₈NOSi⁽¹⁺⁾*CF₃O₃S^(1-)
• CAS NO: 90524-35-9
• Molecular Weight: 415.549
• Mol File: 90524-35-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: C₁₅H₂₈NOSi⁽¹⁺⁾*CF₃O₃S^(1-)(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₅H₂₈NOSi⁽¹⁺⁾*CF₃O₃S^(1-)(90524-35-9)
• EPA Substance Registry System: C₁₅H₂₈NOSi⁽¹⁺⁾*CF₃O₃S^(1-)(90524-35-9)

Safety Data

• Hazardous Substances Data: 90524-35-9(Hazardous Substances Data)

Upstream product

• 5400-82-8 N,N-dimethylbenzylamine N-oxide 
• 69739-34-0 t-butyldimethylsiyl triflate 

Downstream Products

• 61802-83-3 N-methyl-N-benzylbenzamide 
• 611-74-5 N,N-dimethylbenzamide 
• 827-36-1 2-(N,N-dimethylamino)-2-phenylacetonitrile 
• 14321-25-6 (N-benzyl-N-methylamino)acetonitrile 

Relevant articles and documents

Silicon Polonovski Reaction. Formation and Synthetic Application of α-Siloxy Amines

A new and versatile synthetic intermediate, α-siloxy amine was prepared in situ by the base-promoted rearrangement of a siloxyammonium salt obtained by treatment of a tertiary amine N-oxide with trialkylsilyl trifluoromethanesulfonate.The best combination of the base and silylating reagent was found to be methyllithium and t-butyldimethylsilyl trifluoromethanesulfonate.The reactions of α-siloxy amines with acyl halides and haloformates gave the corresponding amides and carbamates in moderate to good yields, respectively.Treatment of α-siloxy amines with acetic acid resulted in a direct dealkylation to free secondary amines.Fluoride induced alkylation of α-siloxy amines using alkyl halides as electrophiles leading to tertiary amines was also examined and demonstrated to be a new transalkylation method of amines.

Base-promoted Rearrangement of Siloxyammonium Salts: a New Method of Dealkylation of Tertiary Amines via Their N-Oxides

Siloxyammonium salts prepared from tertiary amine N-oxides and trialkylsilyl trifluoromethanesulphonate undergo rearrangement in the presence of strong bases to give α-siloxyamines, which can be converted into secondary amine derivatives.