684283-51-0

Usage

Chemical class

Benzimidazole derivatives

Common uses

Catalyst and ligand for organic synthetic reactions

Composition

One benzimidazolium cation and one bromide anion

Salt type

Bromide salt

Role in organic chemistry

Phase-transfer catalyst

Structure and properties importance

Catalysis and organic synthesis component

Upstream product

• 17583-50-5 N-isopropylbenzimidazole 
• 75-26-3 isopropyl bromide 
• 51-17-2 benzoimidazole 
• 582-60-5 5,6-dimethyl-1H-benzo[d]imida-zole 

Downstream Products

• 684283-54-3 1,3-diisopropylbenzimidazol-2-ylidene hydroiodide 
• 1448638-13-8 bromido(1,3-diisopropylbenzimidazolin-2-ylidene)gold(I) 

Relevant academic research and scientific papers

Syntheses, characterizations, and a preliminary comparative cytotoxicity study of gold(I) and gold(III) complexes bearing benzimidazole- and pyrazole-derived N-heterocyclic carbenes

A series of Au(I) and Au(III) mono-, homobis-, and heterobis(carbene) complexes, [AuCl(FPyr)] (2), [Au(iPr2-bimy) 2]PF6 (3), [Au(FPyr)2]PF6 (4), [Au(FPyr)(iPr2-bimy)]PF6 (5), [AuCl 3(iPr2-bimy)] (6), [AuCl3(FPyr)] (7), [AuCl2(iPr2-bimy)2]PF 6 (8), [AuCl2(FPyr)2]PF6 (9), and [AuCl2(FPyr)(iPr2-bimy)]PF6 (10), bearing the benzimidazole-derived iPr2-bimy (1,3-diisopropylbenzimidazolin-2-ylidene) and/or the pyrazole-derived FPyr (1,2,3,4,6,7,8,9-octahydropyridazino[1,2-a]indazolin-11-ylidene) N-heterocyclic carbene (NHC) ligands have been synthesized. Complexes 2-10 have been fully characterized using multinuclei NMR spectroscopy, ESI mass spectrometry, and elemental analysis. X-ray diffraction analyses have been performed on 2, 3, 5, 6, and 8. Together with the previously reported [AuCl(iPr 2-bimy)] (1), the cytotoxic activities of all 10 complexes have been studied in vitro with the NCI-H1666 non-small cell lung cancer cell line. The cationic bis(carbene) complexes 3-5 and 8-10 show better cytotoxicity in comparison to cisplatin. In particular, the heterobis(carbene) complexes 5 and 10 have superior activity, with IC50 values of around 0.2 μM.

Evaluation of arene ruthenium(ii) N-heterocyclic carbene complexes as organometallics interacting with thiol and selenol containing biomolecules

Metal complexes with N-heterocyclic carbene (NHC) ligands have been widely used in catalytic chemistry and are now increasingly considered for the development of new chemical tools and metal based drugs. Ruthenium complexes of the type (p-cymene)(NHC)RuCl2 interacted with biologically relevant thiols and selenols, which resulted in the inhibition of enzymes such as thioredoxin reductase or cathepsin B. Pronounced antiproliferative effects could be obtained provided that an appropriate cellular uptake was achieved. Inhibition of tumor cell growth was accompanied by a perturbation of metabolic parameters such as cellular respiration. The Royal Society of Chemistry 2013.

Indolizy Carbene Ligand. Evaluation of Electronic Properties and Applications in Asymmetric Gold(I) Catalysis

We report herein a new family of carbene ligands based on an indolizine-ylidene (Indolizy) moiety. The corresponding gold(I) complexes are easily obtained from the gold(I)-promoted cyclization of allenylpyridine precursors. Evaluation of the electronic pr

Highly Robust but Surface-Active: An N-Heterocyclic Carbene-Stabilized Au25 Nanocluster

Surface organic ligands play a critical role in stabilizing atomically precise metal nanoclusters in solutions. However, it is still challenging to prepare highly robust ligated metal nanoclusters that are surface-active for liquid-phase catalysis without

N-heterocyclic carbene-catalyzed α-alkylation of ketones with primary alcohols

Several N-heterocyclic carbene precursors are synthesized and used in the α-alkylations of ketones with primary alcohols. With the assistance of a base, these N-heterocyclic carbenes can catalyze the reaction smoothly to furnish dialkylated ketones in good-to-excellent yields.

Palladium complexes with N-heterocyclic carbene ligands as catalysts for the alkoxycarbonylation of olefins

Palladium catalysts, generated from Pd(OAc)2 and 2 equiv of N,N-dialkylbenzimidazolium iodide, are effective for the alkoxycarbonylation of olefins in high yields (>90%). Alkoxycarbonylation of 1-hexene in dimethylacetamide is achieved within 24 h at 110 C using 1 mol % catalyst, 1000 psi CO, and ethanol. Reactions can be prepared in air, without the need of an acid additive to produce ethyl 2-methylhexanoate and ethyl heptanoate in approximately a 2:1 ratio.

A chemical-biological evaluation of rhodium(I) n-heterocyclic carbene complexes as prospective anticancer drugs

Rhodium(I) complexes bearing N-heterocyclic carbene (NHC) ligands have been widely used in catalytic chemistry, but there are very few reports of biological properties of these organometallics. A series of RhI-NHC derivatives with 1,5-cyclooctadiene and CO as secondary ligands were synthesized, characterized, and biologically investigated as prospective antitumor drug candidates. Pronounced antiproliferative effects were noted for all complexes, along with moderate inhibitory activity of thioredoxin reductase (TrxR) and efficient binding to biomolecules (DNA, albumin). Biodistribution studies showed that the presence of albumin lowered the cellular uptake and confirmed the transport of rhodium into the nuclei. Changes in the mitochondrial membrane potential (MMP) were observed as well as DNA fragmentation in wild-type and daunorubicin- or vincristine-resistant Nalm-6 leukemia cells. Overall, these studies indicated that RhI-NHC fragments could be used as partial structures of new antitumor agents, in particular in those drugs designed to address resistant malignant tissues. No resistance to special agents: Rhodium(I) N-heterocyclic carbene (NHC) derivatives with 1,5-cyclooctadiene (COD) and CO as secondary ligands were synthesized, characterized, and biologically investigated as prospective antitumor drug candidates. Pronounced antiproliferative effects were noted for all complexes, along with efficient binding to biomolecules. RhI-NHC fragments could be used as partial structures of new antitumor agents, particularly in drugs designed to address daunorubicin- (DNR) and vincristine (VCR)-resistant malignant tissues (see figure). Copyright

Synthesis of 1,3-dialkylimidazolium and 1,3-dialkylbenzimidazolium salts

A number of N-alkylimidazoles and N-alkylbenzimidazoles were synthesized by reactions of imidazole and benzimidazole with alkyl halides. The reaction rate increases by a factor of 2 to 3 under conditions of microwave activation. Subsequent treatment of the resulting N-alkylazoles with alkyl halides afforded the corresponding 1,3-dialkylimidazolium and 1,3-dialkylbenzimidazolium halides.