917604-39-8

Basic information

• Product Name: 1,3-bis(2,6-diisopropylphenyl)imidazolylium-2-carboxylate
• CAS NO: 917604-39-8
• Molecular Weight: 432.606
• Mol File: 917604-39-8.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: 1,3-bis(2,6-diisopropylphenyl)imidazolylium-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-bis(2,6-diisopropylphenyl)imidazolylium-2-carboxylate(917604-39-8)
• EPA Substance Registry System: 1,3-bis(2,6-diisopropylphenyl)imidazolylium-2-carboxylate(917604-39-8)

Safety Data

• Hazardous Substances Data: 917604-39-8(Hazardous Substances Data)

Usage

Chemical class

Imidazolium class of compounds

Common use

Catalyst in organic synthesis reactions

Specific application

Cross-coupling reactions and C-H activation

Notable feature

Facilitates various chemical transformations

Transformations

Formation of carbon-carbon and carbon-heteroatom bonds

Field of interest

Catalysis

Upstream product

• 124-38-9 carbon dioxide 
• 244187-81-3 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene 
• 24544-04-5 2,6-diisopropylbenzenamine 
• 74663-75-5 1,2-bis(2,6-diisopropylphenylimino)ethane 
• 250285-32-6 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride 

Downstream Products

• 578743-87-0 chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I) 
• 7063-21-0 3-oxo-3-phenylpropanoic acid 

Relevant articles and documents

Solid-state covalent capture of CO2 by using N-heterocyclic carbenes

Capture me! The first report of an N-heterocyclic carbene (NHC) as a solid-state carbon capture reagent is presented. Experimental and theoretical measurements demonstrate the ability of the NHC to react rapidly and stoichiometrically with CO2 at low partial pressures (see scheme). Copyright

N-Heterocyclic Carbene Based Tri-organyl-Zn–Alkyl Cations: Synthesis, Structures, and Use in CO2 Functionalization

Tri-organyl and tricoordinate N-heterocyclic carbene (NHC) Zn–NHC alkyl cations [(nNHC)2Zn-Me]+ (nNHC=C2-bonded-IMes/-IDipp; 3+ and 4+; IMes=1,3-bis(2,4,6-trimethylphenyl)imidazolin-2-ylidene, IDipp=1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene) were first synthesized and structurally characterized by ionization of the corresponding neutral precursors [(nNHC)ZnMe2] with [Ph3C][B(C6F5)4] in the presence of one equivalent of free NHC. Whereas cation [(nIMes)2Zn-Me]+ (3+) is stable, its sterically congested analogue [(nIDipp)2Zn-Me]+ (4+) readily undergoes an nNHC-to-aNHC isomerization in the presence of THF or IDipp to afford the more thermodynamically stable [(aIDipp)(nIDipp)Zn-Me]+ (aIDipp=C4-bonded IDipp, 5+), reflecting the adaptable-to-sterics coordination chemistry of these cations for improved stability. Cations 3+–5+ are the first Zn cations of the type Zn(C)(C′)(C′′)+ (C, C′, C′′=σ-donor carbyl ligand). Kinetic studies combined with DFT calculations agree with an nNHC-to-aNHC process proceeding through the initial deprotonation of 4+ (at a Zn-bonded C4-IDipp moiety) by IDipp. Unlike 3+ and 4+, the rearranged cation 5+ reacts with CO2 through insertion into the Zn–Me bond yielding the corresponding Zn(κ2-OAc)+ cation 6+. Both cations 5+ and 6+ were successfully used in CO2 hydrosilylation catalysis for silylformate formation.

Cycloaddition of COto epoxides catalyzed by N-heterocyclic carbene (NHC)-ZnBrsystem under mild conditions

A very simple and convenient method toward coupling of COwith epoxides catalyzed by NHC/ZnBrhas been developed. This catalytic system exhibits excellent activity and selectivity in the cycloaddition reactions of COto terminal epoxides. The reactions can e