151055-86-6

Basic information

• Product Name: 2-IMIDAZOL-1-YL-BENZALDEHYDE
• Synonyms: 2-IMIDAZOL-1-YL-BENZALDEHYDE;2-IMIDAZOL-1-YL-BENZALDEHYDE, 95+%;2-(1H-pyrazol-1-yl)benzenecarbaldehyde;Zinc02563698
• CAS NO: 151055-86-6
• Molecular Formula: C₁₀H₈N₂O
• Molecular Weight: 172.18
• Product Categories: API intermediates
• Mol File: 151055-86-6.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 316.5 °C at 760 mmHg
• Flash Point: 145.2 °C
• Appearance: Light yellow powder
• Density: 1.15 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.605
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 5.05±0.10(Predicted)
• CAS DataBase Reference: 2-IMIDAZOL-1-YL-BENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-IMIDAZOL-1-YL-BENZALDEHYDE(151055-86-6)
• EPA Substance Registry System: 2-IMIDAZOL-1-YL-BENZALDEHYDE(151055-86-6)

Safety Data

• Hazardous Substances Data: 151055-86-6(Hazardous Substances Data)

Usage

General Description

2-Imidazol-1-yl-benzaldehyde is a chemical compound with a molecular formula C10H8N2O. It is a pale yellow solid that is primarily used as a building block for the synthesis of various pharmaceutical compounds, especially those in the field of antihistamines and other medications that act on the central nervous system. It is also used in the production of dyes and fine chemicals. 2-Imidazol-1-yl-benzaldehyde is known for its mild and pleasant odor and is considered to be relatively stable under normal conditions. Its chemical structure features both an imidazole and an aldehyde group, giving it unique reactivity and properties that make it useful in a variety of synthetic applications.

InChI:InChI=1/C10H8N2O/c13-7-9-3-1-2-4-10(9)12-6-5-11-8-12/h1-8H

Upstream product

• 288-32-4 1H-imidazole 
• 446-52-6 2-Fluorobenzaldehyde 
• 6630-33-7 ortho-bromobenzaldehyde 
• 89-98-5 2-chloro-benzaldehyde 
• 34824-58-3 2-(2-bromophenyl)-1,3-dioxolan 
• 151055-84-4 2-<2-(1H-imidazol-1-yl)phenyl>-1,3-dioxolane 

Downstream Products

• 1033804-91-9 4-chloro-6-[2,2,2-trifluoro-1-(2-imidazol-1-yl-phenyl)ethoxy]pyrimidin-2-ylamine 
• 1600562-76-2 imidazole 
• 1600562-75-1 imidazole 
• 1600562-66-0 3-ethyl-1-(2-(3-isopropoxy-2-(isopropoxycarbonyl)-3-oxoprop-1-en-1-yl)phenyl)-1H-imidazol-3-ium iodide 
• 1600562-65-9 1-(2-(3-isopropoxy-2-(isopropoxycarbonyl)-3-oxoprop-1-en-1-yl)phenyl)-3-methyl-1H-imidazol-3-ium iodide 
• 1600562-64-8 1-(2-(3-ethoxy-2-(ethoxycarbonyl)-3-oxoprop-1-en-1-yl)phenyl)-3-methyl-1H-imidazol-3-ium iodide 
• 1600562-60-4 1-(2-(3-methoxy-2-(methoxycarbonyl)-3-oxoprop-1-en-1-yl)phenyl)-3-methyl-1H-imidazol-3-ium bromide 
• 1600562-59-1 1-(2-(3-methoxy-2-(methoxycarbonyl)-3-oxoprop-1-en-1-yl)phenyl)-3-methyl-1H-imidazol-3-ium iodide 
• 1600562-78-4 imidazole 
• 1600562-77-3 imidazole 
• 1197157-01-9 N₄-(1-(2-(1H-imidazol-1-yl)benzyl)piperidin-4-yl)-N₂-(3-(diethylamino)propyl)quinazoline-2,4-diamine 
• 1033804-90-8 2,2,2-trifluoro-1-(2-imidazol-1-yl-phenyl)ethanol 

Relevant articles and documents

Transition-metal-free insertion of benzyl bromides into 2-(1H-benzo[d]imidazol-1-yl)benzaldehyde: One-pot switchable syntheses of benzo[4,5]imidazo[1,2-a]quinolin-5(7H)-ones and 3-arylquinolin-4-ones mediated by base

A transition-metal-free insertion of benzyl group between aldehyde and imidazole of 2-(1H-benzo[d]imidazol-1-yl)benzaldehyde was achieved for the first time. Two diverse sets of quinolin-4-one derivatives: benzo[4,5]imidazo[1,2-a]quinolin-5(7H)-ones (2) and 3-arylquinolin-4-ones (3) were synthesized based on identical starting materials 2-(1H-benzo[d]imidazol-1-yl)benzaldehydes (1) and benzyl bromides. In the preparations, two key intermediates I and II were involved and might be synthesized in situ through the reaction of an intra-Breslow intermediate with benzyl bromide via an enol attack in the presence of base or a NHC-based enamine attack in the absence of base, respectively, in which the intra-Breslow intermediate might function as a nucleophilic reagent by following two novel different pathways.

Palladium(II) 9,10-phenanthrenequinone N-substituted thiosemicarbazone/semicarbazone complexes as efficient catalysts for N-arylation of imidazole

A series of palladium complexes, [PdCl(L1-4)] (1-4) (L1 = 9,10-phenanthrenequinone thiosemicarbazone, L2 = 9,10-phenanthrenequinone methylthiosemicarbazone, L3 = 9,10-phenanthrenequinone phenylthiosemicarbazone, and L4 = 9,10-phenanthrenequinone semicarbazone), have been synthesized and characterized by elemental analyses, UV-vis, FT-IR, 1H and 13C NMR, and ESI-Mass spectroscopic methods. The catalytic efficiency of the synthesized complexes was examined against N-arylation of imidazole. The system works well with the electron-rich, -neutral, and -deficient aryl halides to afford the products in good to excellent yields. Sterically congested aryl halides and heteroaryl halides have also been used as substrates to provide N-arylated heterocycles. In addition, this methodology can be applicable to other substrates with N-containing heterocycles.

Silver(I)-promoted intramolecular addition of N-heterocyclic carbenes towards unsaturated esters in water

Silver(I)-promoted intramolecular addition reaction between N-heterocyclic carbene and unsaturated esters in water is described. The reaction leads to 1H-imidazo[1,2-a]indole derivatives in moderate to excellent yields.