384344-10-9

Basic information

• Product Name: N-(3,5-dimethylphenyl)-1,1-diphenylmethanimine
• Synonyms: N-(3,5-dimethylphenyl)-1,1-diphenylmethanimine
• CAS NO: 384344-10-9
• Molecular Weight: 285.389
• Mol File: 384344-10-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-(3,5-dimethylphenyl)-1,1-diphenylmethanimine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3,5-dimethylphenyl)-1,1-diphenylmethanimine(384344-10-9)
• EPA Substance Registry System: N-(3,5-dimethylphenyl)-1,1-diphenylmethanimine(384344-10-9)

Safety Data

• Hazardous Substances Data: 384344-10-9(Hazardous Substances Data)

Upstream product

• 108-69-0 3,5-dimethylaminoaniline 
• 16618-52-3 N-(3,5-dimethylphenyl)formamide 
• 20600-56-0 1-isocyano-3,5-dimethylbenzene 
• 595-89-1 Tetraphenyllead 
• 1013-88-3 Benzophenone imine 
• 22445-41-6 3,5-dimethylphenyl iodide 
• 556-96-7 5-bromo-1,3-xylene 

Relevant articles and documents

Amination reactions of aryl halides with nitrogen-containing reagents mediated by palladium/imidazolium salt systems

Nucleophilic N-heterocyclic carbenes have been conveniently used as catalyst modifiers in amination reactions involving aryl chlorides, aryl bromides, and aryl iodides with various nitrogen-containing substrates. The scope of a coupling process using a Pd(0) or Pd(II) source and an imidazolium salt in the presence of a base, KOtBu or NaOH, was tested using various substrates. The Pd2(dba)3/IPr·HCl (1, IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) system presents the highest activity with respect to electron-neutral and electron-rich aryl chlorides. The ligand is also effective for the synthesis of benzophenone imines, which can be easily converted to the corresponding primary amines by acid hydrolysis. Less reactive indoles were converted to N-aryl-substituted indoles using as supporting ligand the more donating SIPr·HCl (5, SIPr = 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene). The Pd(OAc)2/SIPr·HCl/NaOH system is efficient for the N-arylation of diverse indoles with aryl bromides. The general protocol developed has been applied successfully to the synthesis of a key intermediate in the synthesis of an important new antibiotic. Mechanistically, palladium-to-ligand ratio studies strongly support an active species bearing one nucleophilic carbene ligand.

Copper-catalyzed formation of carbon-heteroatom and carbon-carbon bonds

The present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide or amine moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In additional embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between a nitrogen atom of an acyl hydrazine and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of a nitrogen-containing heteroaromatic, e.g., indole, pyrazole, and indazole, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-oxygen bond between the oxygen atom of an alcohol and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. The present invention also relates to copper-catalyzed methods of forming a carbon-carbon bond between a reactant comprising a nucleophilic carbon atom, e.g., an enolate or malonate anion, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. Importantly, all the methods of the present invention are relatively inexpensive to practice due to the low cost of the copper comprised by the catalysts.