36339-13-6

Basic information

• Product Name: 1H-Benzimidazolium, 1,3-bis(phenylmethyl)-, chloride
• CAS NO: 36339-13-6
• Molecular Formula: C21H19N2.Cl
• Molecular Weight: 334.848
• Mol File: 36339-13-6.mol
• Article Data: 16

Chemical Properties

• CAS DataBase Reference: 1H-Benzimidazolium, 1,3-bis(phenylmethyl)-, chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Benzimidazolium, 1,3-bis(phenylmethyl)-, chloride(36339-13-6)
• EPA Substance Registry System: 1H-Benzimidazolium, 1,3-bis(phenylmethyl)-, chloride(36339-13-6)

Safety Data

• Hazardous Substances Data: 36339-13-6(Hazardous Substances Data)

Usage

Structure

A benzimidazole ring with two phenylmethyl substituents and a chloride anion

Type of compound

Quaternary ammonium salt

Use as a catalyst

In organic synthesis, particularly in the formation of carbon-carbon and carbon-nitrogen bonds

Potential properties

Antimicrobial and anticancer

Versatility

Wide range of potential applications in the fields of chemistry and medicine

Upstream product

• 21443-66-3 N¹,N²-dibenzylbenzene-1,2-diamine 
• 122-51-0 orthoformic acid triethyl ester 
• 100-44-7 benzyl chloride 
• 51-17-2 benzoimidazole 
• 4981-92-4 1-benzylbenzimidazole 

Downstream Products

• 20063-33-6 1,3-dibenzyl-2-methyl-2,3-dihydro-1H-benzoimidazole 
• 20493-62-3 1,3-dibenzyl-2-phenyl-2,3-dihydro-1H-benzoimidazole 
• 211240-97-0 1,3-dibenzyl-2-N-phenylthiocarbamoylbenzimidazolium inner salt 
• 1123534-98-4 (Z,Z)-methyl 2-[1,3,4'-tribenzyl-1,3-dihydro-2'-(phenylimino)spiro[2H-benzo[d]imidazole-2,3'(2'H)-thiophen]-5'-ylidene]acetate 
• 1006879-27-1 (E) methyl 1,3-dibenzyl-4'-benzyl-1'-butyl-2'-thioxo-spiro[benzimidazoline-2,3'-pyrrolidin-5'-ylidene]acetate 
• 1006879-29-3 methyl 1,3-dibenzyl-1'-butyl-5'-(2-phenyl)ethyl-2'-thioxo-spiro[benzimidazoline-2,3'-(2,3-dihydro)pyrrol-4'-yl]carboxylate 
• 1204110-64-4 (E)-1,3-dibenzyl-2-(2-methoxycarbonyl-1-(p-methoxyphenyl)amino-1-propenyl)benzimidazolium chloride 
• 586-76-5 4-Bromobenzoic acid 
• 59103-39-8 1,3-dibenzyl-1,3-dihydro-2H-benzo[d]imidazol-2-one 
• 1328886-87-8 C₂₁H₁₉N₂O₉S₃⁽¹⁺⁾*HO₄S^(1-) 
• 24351-21-1 1-ethyl-3-benzylbenzimidazolium iodide 
• 56463-13-9 1-benzyl-3-methyl-1H-benzimidazol-3-ium iodide 

Relevant articles and documents

Quinoidal tetrazines: Formation of a fascinating compound class

A series of different N-heterocyclic carbenes (NHCs) were reacted with 3,6-bis(3′,5′-dimethylpyrazolyl)-tetrazine in the presence of an inorganic carbonate to provide access to a hitherto unprecedented compound class. The formed tetrazine derivatives bearing the NHC in the 3-position and an oxygen in the 6-position show a quinoidal-like structure, according to physical examinations and X-ray crystallography.

Mechanism studies of oxidation and hydrolysis of Cu(I)–NHC and Ag–NHC in solution under air

The decomposition of copper(I)–NHC and silver-NHC complexes in solution under air was studied. The Cu(I)–NHCs were oxidized into urea derivatives and hydrolysed into imidazoliums or benzimidazoliums. The decomposition of Ag–NHC with a saturated backbone led to ring-opening product, while the Ag–NHC with an unsaturated backbone led to imidazolium and Ag-bisNHC complex. The effects of steric property, hydrophilicity, and binding energy of NHC to O2 and H2O on the decomposition of Cu(I)–NHC were studied using theoretical calculations. Steric hindrance played an important role on the stability of Cu(I)–NHC. Pathways for the decomposition of Cu(I)–NHC and Ag–NHC were proposed.

Synthesis of Imidazolidinone, Imidazolone, and Benzimidazolone Derivatives through Oxidation Using Copper and Air

A new synthetic method of urea derivatives using copper and air was developed. These mild conditions provided moderate to very good yields for 15 examples (53-93%), while low yields were obtained with sterically hindered substrates (3 examples). The reaction was found to go through an in situ generated copper-N-heterocyclic carbene, which was then oxidized into cyclic urea derivatives possessing alkyl, benzyl, aryl, hydroxy, Boc-protected, and tertiary amine groups.