1188286-71-6

Basic information

• Product Name: 1,3-bis(2,4,6-trimethylphenyl)imidazolium-4-olate
• Synonyms: 1,3-bis(2,4,6-trimethylphenyl)imidazolium-4-olate
• CAS NO: 1188286-71-6
• Molecular Weight: 320.434
• Mol File: 1188286-71-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1,3-bis(2,4,6-trimethylphenyl)imidazolium-4-olate(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-bis(2,4,6-trimethylphenyl)imidazolium-4-olate(1188286-71-6)
• EPA Substance Registry System: 1,3-bis(2,4,6-trimethylphenyl)imidazolium-4-olate(1188286-71-6)

Safety Data

• Hazardous Substances Data: 1188286-71-6(Hazardous Substances Data)

Upstream product

• 1271-28-9 nickelocene 
• 1188286-70-5 5-hydroxy-1,3-dimesityl-1H-imidazol-3-ium chloride 
• 1188286-70-5 C₂₁H₂₄N₂O*ClH 

Relevant articles and documents

Synthesis, Structures and Properties of Half-Sandwich Nickel(II) Complexes with Backbone-Modified NHC Ligands

A series of seven nickel complexes [Ni(η5-C5H5)(X)(NHC)] (X = Cl or Br; NHC = N-heterocyclic carbene) containing backbone-modified NHC ligands was prepared by treatment of nickelocene with the corresponding NHC·HX salts or, in the case of complex 1h [Ni(η5-C5H5)(Cl)(IMesO)] (IMesO = 4-oxo-1,3-bis(2,4,6-trimethylphenyl)imidazolin-2-ylidene), by deprotection of the corresponding NHC ligand in complex 1g [Ni(η5-C5H5)(Cl)(IMesOPiv)] [IMesOPiv = 4-(pivaloyloxy)-1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene]. Single-crystal X-ray structures were determined for complexes 1d [Ni(η5-C5H5)(Cl)(Bn2-bimy)] (Bn2-bimy = 1,3-dibenzylbenzimidazolin-2-ylidene), 1g and 1h. The coordination spheres around the nickel atoms resemble those of d8 NiL4 square-planar complexes, with Ni-C(Cp) bond length differentiation and C-C bond alternation in Cp ligands being taken into account. Desymmetrization of the five-membered heterocyclic ring and a tautomeric equilibrium were observed for complex 1h. All new complexes are efficient precatalysts in three C-C bond-forming reactions (polymerization of styrene, polymerization of methyl methacrylate, Suzuki-Miyaura cross-coupling). Complexes [Ni(η5-C5H5)(X)(NHC)] featuring backbone-modified NHC ligands were synthesized. Their solid-state structures, solution dynamics, keto-enol equilibria and catalytic activity in C-C bond-forming reactions (polymerization of styrene, polymerization of methyl methacrylate, Suzuki-Miyaura cross-coupling) were investigated.

Imidazol-2-ylidene-4-olate: An anionic N-heterocyclic carbene pre-programmed for further derivatization

The 4-hydroxyimidazolium salt, readily prepared in two steps by acylation of a formamidine and quaternization of the second nitrogen, affords, after deprotonation, the anionic imidazol-2-ylidene-4-olate, which can be complexed to a transition metal and st