25660-38-2

Basic information

• Product Name: 1H-Benzimidazole,1-(3-pyridinyl)-(9CI)
• Synonyms: 1H-Benzimidazole,1-(3-pyridinyl)-(9CI);1-(3-pyridinyl)-1H-Benzimidazole
• CAS NO: 25660-38-2
• Molecular Formula: C₁₂H₉N₃
• Molecular Weight: 195.21996
• Product Categories: BENZIMIDAZOLE
• Mol File: 25660-38-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 89-91 °C
• Boiling Point: 394.5±44.0 °C(Predicted)
• Appearance: /
• Density: 1.21±0.1 g/cm3(Predicted)
• PKA: 3.99±0.12(Predicted)
• CAS DataBase Reference: 1H-Benzimidazole,1-(3-pyridinyl)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Benzimidazole,1-(3-pyridinyl)-(9CI)(25660-38-2)
• EPA Substance Registry System: 1H-Benzimidazole,1-(3-pyridinyl)-(9CI)(25660-38-2)

Safety Data

• Hazardous Substances Data: 25660-38-2(Hazardous Substances Data)

Usage

Structure

Benzimidazole derivative with a pyridine group attached to the benzimidazole ring

Usage

Synthesis of various pharmaceuticals and agrochemicals, versatile reactivity and building block in organic synthesis

Biological activities

Potential antifungal agent and potential use in the treatment of various diseases

Value

Unique structure and properties make it a valuable tool in the development of new and innovative chemical and pharmaceutical products.

Upstream product

• 626-55-1 3-Bromopyridine 
• 51-17-2 benzoimidazole 
• 845885-86-1 3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl) pyridine 
• 131534-65-1 pyridine-3-boronic acid 1,3-propanediol cyclic ester 
• 1692-25-7 3-pyridylboronic acid 

Downstream Products

• 1399480-28-4 5,6-diphenylbenzo[4,5]imidazo[1,2-a][1,5]naphthyridine 
• 1399480-31-9 5,6-diphenylbenzo[4,5]imidazo[1,2-a][1,7]naphthyridine 

Relevant articles and documents

Chan-Lam cross-coupling reaction based on the Cu2S/TMEDA system

A catalyst based on the readily available Cu2S/TMEDA system using a stable copper(I) source was developed for the Chan-Lam cross-coupling reaction. The capability of the catalyst was demonstrated with 1H-benzo[d]imidazol-2(3H)-one, 1H-benzo[d]imidazole, and 1H-imidazole together with electron-deficient, electron-rich, and sterically demanding boronic acids at room temperature in the presence of atmospheric oxygen to give the cross-coupling products in moderate to excellent yields. In addition, the coupling reaction of 1H-benzo[d]imidazole with several pinacol or neopentylglycol boronates indicated further potential of the catalyst. The reaction conditions tolerate the hydroxyl and bromo functional groups. The catalytic system also enables to synthesize the mono-N-substituted anilines from primary aliphatic amines. However, the two model compounds for the secondary and aromatic amines, piperidine and aniline, do not react. Two sterically demanding products with the restricted C–N bond rotation, synthesized by the N-arylation of 1H-benzo[d]imidazol-2(3H)-one with o-tolylboronic acid, enabled to confirm the atropisomers prepared by the Chan-Lam cross-coupling reaction. Furthermore, an example of one-pot Chan-Lam and Suzuki-Miyaura reaction has been reported.

Ligand-free copper-catalysed coupling reaction of heteroaryl bromides with imidazole and benzimidazole

The synthesis of N-heteroarylimidazoles by coupling heteroaryl bromides with imidazole or benzimidazole under relatively mild conditions using the stable and readily available copper(II) acetate as catalyst and cesium carbonate as base is reported to give products in moderate to good yields.

Copper promoted C-N and C-O bond cross-coupling with phenyl and pyridylboronates

Acyclic and cyclic esters, as well as anhydride (boroxine) of phenylboronic acids are efficient phenylating agents in copper promoted C-N and C-O bond cross-coupling reactions. The first successful C-N cross-coupling of a heterocyclic boronate with heteroarenes, such as indazole, has been demonstrated.