1428963-13-6

Basic information

• Product Name: (E)-N,N-dimethyl-4-(2-(trimethylsilyl)vinyl)aniline
• Synonyms: (E)-N,N-dimethyl-4-(2-(trimethylsilyl)vinyl)aniline
• CAS NO: 1428963-13-6
• Molecular Weight: 219.402
• Mol File: 1428963-13-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (E)-N,N-dimethyl-4-(2-(trimethylsilyl)vinyl)aniline(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-N,N-dimethyl-4-(2-(trimethylsilyl)vinyl)aniline(1428963-13-6)
• EPA Substance Registry System: (E)-N,N-dimethyl-4-(2-(trimethylsilyl)vinyl)aniline(1428963-13-6)

Safety Data

• Hazardous Substances Data: 1428963-13-6(Hazardous Substances Data)

Upstream product

• 41309-43-7 (2-bromovinyl)trimethylsilane 
• 7353-91-5 4-dimethylaminophenylmagnesium bromide 
• 617-86-7 triethylsilane 
• 17573-94-3 4-ethynyl-N,N-dimethylaniline 
• 16029-98-4 trimethylsilyl iodide 
• 2039-80-7 N,N-dimethy-4-vinylaniline 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 1068-69-5 Tris(trimethylsilyl)methane 
• 1613-99-6 (E)-N,N-dimethyl-4-((phenylimino)methyl)aniline 

Downstream Products

• 89510-55-4 1-p-nitrophenyl-4-p-nitrophenylbuta-1E,3E-diene 
• 67309-70-0 4-<4-<4-N,N-dimethylaminophenyl>-butadienyl>-nitrobenzene 

Relevant articles and documents

Synthesis of multinuclear Rh(I) complexes bearing triazolylidenes and their application in C-C and c-Si bond forming reactions

Multidentate carbene ligands are valuable frameworks for the preparation of carbene complexes displaying higher nuclearity. In the present work, we report the synthesis of a series of mono- to tetra-[Rh(COD)I] complexes (3a- d) supported by mesoionic triazol-5-ylidenes. The general synthetic procedure involves the one step reaction of the appropriate triazolium (2a-d) salt in the presence of KHMDS and stoiquiometric amounts of the rhodium(I) precursor. Treatment of complexes 3a-d with an excess of carbon monoxide allows for the quantitative preparation of complexes 4a-d featuring a [Rh(CO)2I] fragment used for the detemination of the donor properties of the new triazolylidene ligands. All complexes have been fully characterized by means of 1H and 13C NMR spectroscopy, melting point, elemental analysis, and in the case of complex 3a, by X-ray crystallography. Comparison of the catalytic activity of the new rhodium complexes in C-C and C-Si bond forming processes demonstrate the enhanced performance of the tetranuclear species suggesting the possibility of strong cooperative effects in these multinuclear complexes.

Stereoselective peterson olefinations from bench-stable reagents and N-phenyl imines

The synthesis of bench-stable α,α-bis(trimethylsilyl)toluenes and tris(trimethylsilyl)methane is described and their use in stereoselective Peterson olefinations has been achieved with a wide substrate scope. Product stereoselectivity was poor with carbonyl electrophiles (E/Z ～1:1 to 4:1) though this was significantly improved by employing the corresponding substituted N-benzylideneaniline (up to 99:1) as an alternative electrophile. The olefination byproduct was identified as N,N-bis(trimethylsilyl)aniline and could be easily separated from product by aqueous acid extraction. Evidence for an autocatalytic cycle has been obtained.

Oxidative cross-coupling of vinylsilanes in water

Palladium-promoted cross-dimerization reaction of alkenylsilanes is reported for the first time, which is also one of the very first studies on oxidative cross-coupling between vinylic organometallic reagents. The reaction occurs at room temperature in aqueous micelles and represents a convenient access to all-trans push-pull butadienes.