132034-50-5

Basic information

• Product Name: (Z)-2,6-dimethylphenyl-1'-methyl-2'-methoxyethyl-imine
• Synonyms: (Z)-2,6-dimethylphenyl-1'-methyl-2'-methoxyethyl-imine
• CAS NO: 132034-50-5
• Molecular Weight: 191.273
• Mol File: 132034-50-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (Z)-2,6-dimethylphenyl-1'-methyl-2'-methoxyethyl-imine(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-2,6-dimethylphenyl-1'-methyl-2'-methoxyethyl-imine(132034-50-5)
• EPA Substance Registry System: (Z)-2,6-dimethylphenyl-1'-methyl-2'-methoxyethyl-imine(132034-50-5)

Safety Data

• Hazardous Substances Data: 132034-50-5(Hazardous Substances Data)

Upstream product

• 5878-19-3 Methoxyacetone 
• 87-62-7 2,6-dimethylaniline 

Downstream Products

• 118604-66-3 (R)-N-(1-methyl-2-methoxyethyl)-2,6-dimethylaniline 
• 118604-67-4 S-2,6-dimethyl-N-(2-methoxy-1-methylethyl)-aniline 
• 60148-77-8 N-(2',6'-dimethylphenyl)-1-methoxymethylethylamine 

Relevant articles and documents

Chiral Xyliphos Complexes for the Catalytic Imine Hydrogenation Leading to the Metolachlor Herbicide: Isolation of Catalyst-Substrate Adducts

Iridium complexes relevant to the catalytic enantioselective hydrogenation of 2-methyl-6-ethylphenyl-1′-methyl-2′-methoxyethylimine (MEA-imine, 1) in the Syngenta Metolachlor (3) process were prepared and characterized. Reaction of the diphosphane (S)-1-[(R)-2-(diphenylphosphanyl)ferrocenyl]ethyldi(3,5-xylyl)phosphane ((S)-(R)-Xyliphos, (S)-(R)-4) with [Ir2(μ-Cl) 2(cod)2] (cod = 1,5-cyclooctadiene) afforded [Ir(Cl)(cod){(S)-(R)-4}] (7), which reacted with AgBF4 to form [Ir(cod){(S)-(R)-4}]BF4 (8). Complexes 7 and 8 reacted with iodide to yield [Ir(I)(cod){(S)-(R)-4}] (9). When 9 was treated with one and two equivalents of HBF4, two isomers of the cationic IrIII iodo hydrido complex [Ir(I)(H)-(cod){(S)-(R)-4}]BF4 were isolated (10 and 11, respectively). Complex 9 was oxidized with one equivalent of I2 to give the iodo-bridged dinuclear species [Ir 2I2(μ-I)3{(S)-(R)-4}2)] I (12). [Ir2(μ-Cl)2(coe)4] (coe=cyclooctene) reacted with (S)-(R)4 to yield the chlorobridged dinuclear complex [Ir2(μ-Cl)2{(S)-(R)-4}2] (13). Complexes 7-12 were structurally characterized by single-crystal X-ray diffraction and tested as single-component catalyst precursors for enantioselective hydrogenation of MEA-imine. Complex 10 and dinuclear complex 12 gave the best catalytic results. Efforts were also directed at isolating substrate- or product-catalyst adducts: Treatment of 8 with 2,6-dimethylphenyl-1′-methyl-2′-methoxyethylimine (DMA-imine, 14, a model for 1) under H2 allowed four isomers of [Ir(H) 2{(S)-(R)-4}(14)]BF4 (18-21) to be isolated. These analytically pure isomers were fully characterized by 2D NMR techniques. X-ray structural analysis of an IrI-imine adduct, namely, [Ir(C 2H4)2(14)]BF4 (25), which was prepared by reacting [IrCl(C2H4)4] with [Ag(14)2]BF4 (16), confirmed the κ2 coordination mode of imine 14.