3805-38-7

Basic information

• Product Name: 1,2,3-trimethyl-1H-benzimidazol-3-ium iodide
• Synonyms: 1,2,3-Trimethyl-1H-3,1-benzimidazol-3-ium iodide; 1H-3,1-benzimidazolium, 1,2,3-trimethyl-, iodide (1:1)
• CAS NO: 3805-38-7
• Molecular Formula: C₁₀H₁₃N₂*I
• Molecular Weight: 288.1281
• Mol File: 3805-38-7.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: 1,2,3-trimethyl-1H-benzimidazol-3-ium iodide(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3-trimethyl-1H-benzimidazol-3-ium iodide(3805-38-7)
• EPA Substance Registry System: 1,2,3-trimethyl-1H-benzimidazol-3-ium iodide(3805-38-7)

Safety Data

• Hazardous Substances Data: 3805-38-7(Hazardous Substances Data)

Usage

Structure

A derivative of benzimidazole, a heterocyclic aromatic organic compound, with three methyl groups attached to the first, second, and third carbon atoms.

Appearance

White to off-white crystalline powder

Potential applications

a. Organic synthesis
b. Reactant in chemical reactions
c. Pharmaceutical research
d. Reagent in organic chemistry

Upstream product

• 615-15-6 2-Methyl-1H-benzimidazole 
• 74-88-4 methyl iodide 
• 2876-08-6 1,2-dimethyl-1H-benzimidazole 
• 603-35-0 triphenylphosphine 

Downstream Products

• 110442-31-4 4-[(1,3-dimethyl-1,3-dihydro-benzimidazol-2-yliden)-ethylidene]-2-phenyl-4H-oxazol-5-one 
• 116081-83-5 2-[4-(N-acetyl-anilino)-buta-1,3-dienyl]-1,3-dimethyl-benzimidazolium; iodide 
• 110395-23-8 2-[2-(N-acetyl-anilino)-vinyl]-1,3-dimethyl-benzimidazolium; iodide 
• 4120-60-9 acetic acid-(N-methyl-2-methylamino-anilide) 
• 21337-25-7 2-(4-dimethylamino-styryl)-1,3-dimethyl-benzimidazolium; iodide 
• 110152-77-7 2-[(4-dimethylamino-phenylimino)-methyl]-1,3-dimethyl-benzimidazolium; iodide 
• 1626-09-1 2,7-octanedione 
• 3213-79-4 N,N'-dimethyl-1,2-phenylenediamine 
• 1849-01-0 1-methyl-2-benzimidazolone 
• 59066-63-6 (E)-1-methyl-2-styryl-1H-benzo[d]imidazole 
• 58758-09-1 (E)-2-styryl-1H-benzo[d]imidazole 
• 109649-34-5 2-anilino-5-[(1,3-dimethyl-1,3-dihydro-benzimidazol-2-yliden)-ethylidene]-thiazol-4-one 
• 122724-78-1 5-[(1,3-dimethyl-1,3-dihydro-benzimidazol-2-yliden)-ethylidene]-3-phenyl-2-phenylimino-thiazolidin-4-one 
• 119641-51-9 5-[6-(1,3-dimethyl-1,3-dihydro-benzimidazol-2-ylidene)-hexa-2,4-dienylidene]-3-phenyl-2-phenylimino-thiazolidin-4-one 

Relevant articles and documents

-

-

The regioselectivity and synthetic mechanism of 1,2-benzimidazole squaraines: Combined experimental and theoretical studies

In this paper, a synthetic method to produce 1,2-benzimidazole squaraines with a yield of up to 89% is developed. It is found that both strong organic and inorganic bases have a satisfactory catalytic activity for this reaction. Theoretical studies provide detailed explanations for the 1,2 versus 1,3 condensation regiochemistry of the squaraines. The experimental and theoretical studies agree well with each other, paving a practical way to efficiently synthesize 1,2-squaraines. The Royal Society of Chemistry.

Br?nsted Basicities and Nucleophilicities of N-Heterocyclic Olefins in Solution: N-Heterocyclic Carbene versus N-Heterocyclic Olefin. Which Is More Basic, and Which Is More Nucleophilic?

A Br?nsted basicity scale comprising nine representative N-heterocyclic olefins (NHOs) was established by measuring the equilibrium acidities of their corresponding precursors in DMSO using an ultraviolet-visible spectroscopic method. The basicities (pKaHs) of the investigated NHOs cover a range from 14.7 to 24.1. The basicities of unsaturated NHOs are stronger than those of their N-heterocyclic carbene (NHC) analogues; however, the basicities for the saturated ones are much weaker than those of their NHC analogues, which is largely due to the aromatization effect that intrinsically influences the acidic dissociations of NHC and NHO precursors. The nucleophilicities of four NHOs were measured photometrically by monitoring the kinetics of reactions of these NHOs with common reference electrophiles for quantifying nucleophilic reactivities. In general, the nucleophilicity of the NHOs is much stronger than that of commonly used Lewis bases such as Ph3P or DMAP [4-(dimethylamino)pyridine] but weaker than that of their NHC analogues; however, caution should be taken when generalizing this conclusion to a wide range of electrophiles with distinctively electronic and structural properties.

Benzimidazoles as Metal-Free and Recyclable Hydrides for CO2 Reduction to Formate

We report a novel metal-free chemical reduction of CO2 by a recyclable benzimidazole-based organo-hydride, whose choice was guided by quantum chemical calculations. Notably, benzimidazole-based hydride donors rival the hydride-donating abilities of noble-metal-based hydrides such as [Ru(tpy)(bpy)H]+ and [Pt(depe)2H]+. Chemical CO2 reduction to the formate anion (HCOO-) was carried out in the absence of biological enzymes, a sacrificial Lewis acid, or a base to activate the substrate or reductant. 13CO2 experiments confirmed the formation of H13COO- by CO2 reduction with the formate product characterized by 1H NMR and 13C NMR spectroscopy and ESI-MS. The highest formate yield of 66% was obtained in the presence of potassium tetrafluoroborate under mild conditions. The likely role of exogenous salt additives in this reaction is to stabilize and shift the equilibrium toward the ionic products. After CO2 reduction, the benzimidazole-based hydride donor was quantitatively oxidized to its aromatic benzimidazolium cation, establishing its recyclability. In addition, we electrochemically reduced the benzimidazolium cation to its organo-hydride form in quantitative yield, demonstrating its potential for electrocatalytic CO2 reduction. These results serve as a proof of concept for the electrocatalytic reduction of CO2 by sustainable, recyclable, and metal-free organo-hydrides.