1401032-88-9

Basic information

• Product Name: 1-(2,4-dinitrophenyl)-3-methylimidazolium triflate
• CAS NO: 1401032-88-9
• Molecular Weight: 398.276
• Mol File: 1401032-88-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-(2,4-dinitrophenyl)-3-methylimidazolium triflate(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,4-dinitrophenyl)-3-methylimidazolium triflate(1401032-88-9)
• EPA Substance Registry System: 1-(2,4-dinitrophenyl)-3-methylimidazolium triflate(1401032-88-9)

Safety Data

• Hazardous Substances Data: 1401032-88-9(Hazardous Substances Data)

Upstream product

• 14545-01-8 N-2,4-dinitrophenylimidazole 
• 333-27-7 methyl trifluoromethanesulfonate 

Relevant articles and documents

N-heterocyclic carbenes with a N-2,4-dinitrophenyl substituent: Comparison with PPh3 and IPr

Synthesis and characterization of N-heterocyclic carbenes (NHCs) bearing a 2,4-dinitrophenyl (DNP) substituent on an NHC framework were performed. The treatment of 1-(2,4-dinitrophenyl)-1H-imidazole (1) with 1-bromo-2,4- dinitrobenzene or methyl triflate afforded imidazolium salts 2a?HBr or 2b?HOTf, respectively, which were corresponding precursors of NHC ligands 1,3-bis(2,4-dinitrophenyl)-1H-imidazol-2-ylidene (2a) and 1-(2,4-dinitrophenyl)- 3-methyl-1H-imidazol-2-ylidene (2b). Rh and Au complexes-RhCl(2a)(cod) [3a (cod = 1,5-cyclooctadiene)], RhCl(2b)(cod) (3b), RhCl(2a)(CO)2 (4a), RhCl(2b)(CO)2 (4b), and AuCl(2a) (5a)-were synthesized using 2a?HBr and 2b?HOTf. IR, NMR, and crystallographic analysis of the Rh complexes demonstrated that the DNP substituent remarkably decreased the σ-donating ability of the carbenic carbon and increased the π-accepting ability. In addition, IR spectroscopy of Rh dicarbonyl complexes revealed that the average CO stretching frequency of 2a was equal to that of PPh3. Au complex 5a exhibited a significantly higher catalytic activity than AuCl(PPh3) 5d in the Au(I)-catalyzed hydroalkoxylation of cyclohexene. The computational analysis of the Au(I) complexes supported the experimental data, and the results suggested that the Au-Ccarbene π-back-bonding interaction energy of 5a was 17-20% larger than that of 5d.