18840-19-2

Basic information

• Product Name: Benzenamine, N,N-dimethyl-4-(triphenylsilyl)-
• CAS NO: 18840-19-2
• Molecular Formula: C26H25NSi
• Molecular Weight: 379.577
• Mol File: 18840-19-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Benzenamine, N,N-dimethyl-4-(triphenylsilyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenamine, N,N-dimethyl-4-(triphenylsilyl)-(18840-19-2)
• EPA Substance Registry System: Benzenamine, N,N-dimethyl-4-(triphenylsilyl)-(18840-19-2)

Safety Data

• Hazardous Substances Data: 18840-19-2(Hazardous Substances Data)

Upstream product

• 18840-16-9 N,N-dimethyl-2-(triphenylsilyl)aniline 
• 76-86-8 Triphenylsilyl chloride 
• 698-00-0 2-bromo-N,N-dimethylaniline 
• 121-69-7 N,N-dimethyl-aniline 
• 789-25-3 HSiPh₃ 
• 78-10-4 tetraethoxy orthosilicate 
• 591-51-5 phenyllithium 
• 13190-50-6 4-dimethylaminophenyllithium 
• 10026-04-7 tetrachlorosilane 
• 698-70-4 4-Iodo-N,N-dimethylaniline 

Downstream Products

• 18737-40-1 4-bromophenyltriphenylsilane 
• 18840-20-5 N,N-dimethyl-3-triphenylsilanyl-aniline; hydrochloride 
• 18762-99-7 ph3Si(ph-3-N(et-2-OH)2) 
• 18840-18-1 ph3Si(ph-3-Nme₂) 
• 76-86-8 Triphenylsilyl chloride 

Relevant articles and documents

Ruthenium-Catalyzed Isomerization of ortho-Silylanilines to Their para Isomers

The catalytic ortho to para transposition of a silyl group in aniline derivatives is described. [RuCl2(p-cymene)]2/BINAP in conjunction with a Cu(OAc)2 additive serves as a potent catalytic system. This method is also applicable to the isomerization of 2-silylpyrrole derivatives to the corresponding 3-silyl isomers.

Friedel-Crafts-Type Intermolecular C-H Silylation of Electron-Rich Arenes Initiated by Base-Metal Salts

An electrophilic aromatic substitution (SEAr) with a catalytically generated silicon electrophile is reported. Essentially any commercially available base-metal salt acts as an initiator/catalyst when activated with NaBArF4. The thus-generated Lewis acid then promotes the SEAr of electron-rich arenes with hydrosilanes but not halosilanes. This new C-H silylation was optimized for FeCl2 /NaBArF4, affording good yields at catalyst loadings as low as 0.5 mol %. The procedure is exceedingly straightforward and comes close to typical Friedel-Crafts methods, where no added base is needed to absorb the released protons.