199604-04-1

Basic information

• Product Name: N-trimethylsilyl-4-trifluoromethylbenzaldimine
• Synonyms: N-trimethylsilyl-4-trifluoromethylbenzaldimine
• CAS NO: 199604-04-1
• Molecular Weight: 245.32
• Mol File: 199604-04-1.mol

Chemical Properties

• CAS DataBase Reference: N-trimethylsilyl-4-trifluoromethylbenzaldimine(CAS DataBase Reference)
• NIST Chemistry Reference: N-trimethylsilyl-4-trifluoromethylbenzaldimine(199604-04-1)
• EPA Substance Registry System: N-trimethylsilyl-4-trifluoromethylbenzaldimine(199604-04-1)

Safety Data

• Hazardous Substances Data: 199604-04-1(Hazardous Substances Data)

Upstream product

• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 4039-32-1 lithium hexamethyldisilazane 

Downstream Products

• 503112-03-6 (R,R)-1,2-bis(4-trifluoromethylphenyl)-1,2-ethanediamine 
• 1443049-95-3 (R)-N-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)(4-(trifluoromethyl)phenyl)methyl)pivalamide 
• 455-18-5 4-CF₃C₆H₄CN 

Relevant articles and documents

Chiral phosphoric acid catalyzed enantioselective [4 + 2] cycloaddition reaction of α-fluorostyrenes with imines

An enantioselective [4 + 2] cycloaddition reaction of α-fluorostyrenes with N-benzoyl imines was demonstrated using a chiral phosphoric acid catalyst. Cycloaddition products having fluorine functionality were formed in high yields with excellent diastereo

Access to nitriles from aldehydes mediated by an oxoammonium salt

A scalable, high yielding, rapid route to access an array of nitriles from aldehydes mediated by an oxoammonium salt (4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate) and hexamethyldisilazane (HMDS) as an ammonia surrogate has been developed. The reaction likely involves two distinct chemical transformations: reversible silyl-imine formation between HMDS and an aldehyde, followed by oxidation mediated by the oxoammonium salt and desilylation to furnish a nitrile. The spent oxidant can be easily recovered and used to regenerate the oxoammonium salt oxidant.

Catalytic enantioselective one-pot aminoborylation of aldehydes: A strategy for construction of nonracemic α-amino boronates

We report a strategy for the conversion of aldehydes to enantiomerically enriched α-amino boronates through the intermediacy of in situ-generated silylimines. This transformation is brought about by Pt-catalyzed asymmetric addition of B2(pin)s

Convenient Access to Primary Amines by Employing the Barbier-Type Reaction of N-(Trimethylsilyl)imines Derived from Aromatic and Aliphatic Aldehydes

A new versatile preparation of primary amines via benzylation of aromatic and aliphatic aldimines is described. Sonochemical and traditional methods for generation of the reactive intermediates are compared and contrasted. Competitive reactions were analyzed via free energy relationships to support the proposed alkylative mechanism.

N-alkyloxycarbonyl-3-aryloxaziridines: Their preparation, structure, and utilization as electrophilic amination reagents

This paper reports the synthesis of a series of N-protected oxaziridines (N-Moc, Boc, Z or Fmoc) and discusses their ability to deliver their N-alkoxycarbonyl fragment to amines, enolates, sulfur, and phosphorus nucleophiles (electrophilic amination). These oxaziridines are prepared by oxidation of the corresponding imines with oxone or anhydrous MCPBA lithium salt as the source of oxygen. They transfer their N-protected fragment to primary and secondary amines to give protected hydrazines in fair to excelent yield. The nitrogen transfer to free amino acids (in form of their R4N+ salts) is particularly fast, even at low temperature, providing L (or D) N-protected α-hydrazino acids. Enolates are C-aminated to give N-protected α-amino ketones, esters, or amides in modest yield, due to a side aldol reaction of the unreacted enolate with the released benzaldehyde. With tertiary amines (Et3N), sulfides (PhSMe), and phosphines (Ph3P), amination and oxidation proceed in a parallel way; the amount of amination product increases when the temperature is lowered (kinetic control). Some of the factors that can orient the oxaziridine reactivity towards amination or oxidation of nucleophiles are considered.