1515644-59-3

Basic information

• Product Name: (((2-methylphenyl)(1H-pyrrol-2-ylmethylene)-amine)(-H))AlMe₂
• CAS NO: 1515644-59-3
• Molecular Weight: 240.284
• Mol File: 1515644-59-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (((2-methylphenyl)(1H-pyrrol-2-ylmethylene)-amine)(-H))AlMe₂(CAS DataBase Reference)
• NIST Chemistry Reference: (((2-methylphenyl)(1H-pyrrol-2-ylmethylene)-amine)(-H))AlMe₂(1515644-59-3)
• EPA Substance Registry System: (((2-methylphenyl)(1H-pyrrol-2-ylmethylene)-amine)(-H))AlMe₂(1515644-59-3)

Safety Data

• Hazardous Substances Data: 1515644-59-3(Hazardous Substances Data)

Upstream product

• 139954-09-9 N-(2'-methylphenyl)pyrrole-2-aldimine 
• 75-24-1 trimethylaluminum 
• 95-53-4 o-toluidine 
• 1003-29-8 2-pyrrole aldehyde 

Relevant articles and documents

Monomethylaluminum and dimethylaluminum pyrrolylaldiminates for the ring-opening polymerization of rac-lactide: Effects of ligand structure and coordination geometry

Two series of aluminum alkyl complexes supported by pyrrolylaldiminate ligands, LAlMe2 (1a-7a) and L2AlMe (1b-7b), were successfully synthesized and characterized by NMR spectroscopy and elemental analysis. Reactions of trimethylaluminum with the corresponding pyrrolylaldiminate ligands in the molar ratios of 1:1 and 1:2 yielded dimethylaluminum pyrrolylaldiminates (1a-7a) and monomethylaluminum pyrrolylaldiminates (1b-7b), respectively, in good yields. The structure of 3b, determined by single-crystal X-ray diffraction, displayed a distorted trigonal bipyramidal geometry with the τ value of 0.65. Upon addition of 1 equivalent of benzyl alcohol, all complexes promoted the living ring-opening polymerization of rac-lactide with a good control over molecular weights and polydispersities. Complexes 6a and 7a were found to efficiently mediate the immortal polymerization in the presence of excess equivalents of benzyl alcohol (up to 5 equivalents), as evidenced by the narrow PDI values and the good agreement between the experimental Mn values and monomer/benzyl alcohol ratios. The steric and electronic effects of the imine nitrogen substituents had a strong influence on the polymerization activities both in catalytic activity and polymer microstructure. The catalytic activity decreased as follows: 4-Me-C6H4 (3) > C6H5 (1) ≈ 4-F-C6H4 (2) ≈ 2-Me-C6H4 (5) > 4-OMe-C6H4 (4) ? 2-tBu-C 6H4 (6) > adamantyl (7). In comparison, the catalytic activity of the monomethylaluminum complex is slightly higher than that of the dimethylaluminum counterpart. The polymerization of rac-lactide by 6b yielded heterotactically enriched polylactide (Pr = 0.60) whereas the isotactic-enriched polymer (Pm = 0.74) was obtained from 7b. The Royal Society of Chemistry 2014.