1016-93-9

Basic information

• Product Name: 1H-IMIDAZO[4,5-B]PYRIDINE, 2-PHENYL-
• Synonyms: 1H-IMIDAZO[4,5-B]PYRIDINE, 2-PHENYL-;3H-Imidazo[4,5-b]pyridine, 2-phenyl-
• CAS NO: 1016-93-9
• Molecular Formula: C₁₂H₉N₃
• Molecular Weight: 195.22
• Mol File: 1016-93-9.mol
• Article Data: 25

Chemical Properties

• Melting Point: 291-293℃
• Boiling Point: 356.6±25.0 °C(Predicted)
• Appearance: /
• Density: 1.26
• Storage Temp.: 2-8°C
• PKA: 7.48±0.20(Predicted)
• CAS DataBase Reference: 1H-IMIDAZO[4,5-B]PYRIDINE, 2-PHENYL-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-IMIDAZO[4,5-B]PYRIDINE, 2-PHENYL-(1016-93-9)
• EPA Substance Registry System: 1H-IMIDAZO[4,5-B]PYRIDINE, 2-PHENYL-(1016-93-9)

Safety Data

• Hazardous Substances Data: 1016-93-9(Hazardous Substances Data)

Usage

General Description

1H-Imidazo[4,5-b]pyridine, 2-phenyl- is a chemical compound with the molecular formula C12H9N3. It is a heterocyclic aromatic organic compound with a fused imidazo[4,5-b]pyridine and phenyl ring structure. 1H-Imidazo[4,5-b]pyridine, 2-phenyl- has potential applications in pharmaceutical and medicinal chemistry, as it is a core structure found in a variety of biologically active compounds, including anti-inflammatory, anti-cancer, and anti-viral agents. Its unique structure and biological activity make it a valuable target for drug discovery and development. Additionally, the compound may also be used as a reagent in organic synthesis for the preparation of other imidazo[4,5-b]pyridine-based compounds with diverse properties and potential applications.

Upstream product

• 452-58-4 2,3-Diaminopyridine 
• 65-85-0 benzoic acid 
• 119-61-9 benzophenone 
• 495-40-9 propiophenone 
• 98-86-2 acetophenone 
• 93-55-0 1-phenyl-propan-1-one 
• 63581-31-7 N₃-benzylidenepyridine-2,3-diamine 
• 100-52-7 benzaldehyde 
• 39856-58-1 3-amino-2-bromopyridine 
• 1480-87-1 2-fluoro-3-nitropyridine 
• 100-46-9 benzylamine 
• 54231-35-5 3-fuoro-2-nitropyridine 
• 100-51-6 benzyl alcohol 
• 2876-13-3 N-benzylpyridinium chloride 

Relevant articles and documents

Rapid synthesis of imidazo[4,5-b]pyridine containing polycyclics by means of palladium-catalyzed amidation of 2-chloro-3-nitropyridine

Regioselective nucleophilic substitution of 2-chloro 3-nitropyridine with heterocyclic amides under Pd-catalyzed reaction conditions as described by Buchwald yielded imidazo [4,5-b] pyridine-containing polycyclics as novel scaffolds.

Sodium sulfide: A sustainable solution for unbalanced redox condensation reaction between o -nitroanilines and alcohols catalyzed by an iron-sulfur system

Unbalanced redox condensation reaction between o-nitroanilines and alcohols, leading to benzimidazole and quinoxaline heterocycles can be efficiently promoted and catalyzed by sodium sulfide (40 mol%) in combination with iron(III) chloride hexahydrate (1 mol%). Beside the role as a precursor for the iron-sulfur (Fe/S) catalyst formation, hydrated sodium sulfide was shown to be an excellent noncompetitive, multi-electron reducing agent.

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Heteroaromatic Inhibitors of the Astacin Proteinases Meprin α, Meprin β and Ovastacin Discovered by a Scaffold-Hopping Approach

Astacin metalloproteinases, in particular meprins α and β, as well as ovastacin, are emerging drug targets. Drug-discovery efforts have led to the development of the first potent and selective inhibitors in the last few years. However, the most recent compounds are based on a highly flexible tertiary amine scaffold that could cause metabolic liabilities or decreased potency due to the entropic penalty upon binding to the target. Thus, the aim of this study was to discover novel conformationally constrained scaffolds as starting points for further inhibitor optimization. Shifting from flexible tertiary amines to rigid heteroaromatic cores resulted in a boost in inhibitory activity. Moreover, some compounds already exhibited higher activity against individual astacin proteinases compared to recently reported inhibitors and also a favorable off-target selectivity profile, thus qualifying them as very suitable chemical probes for target validation.

A one-step synthesis of substituted benzo- and pyridine-fused 1H-imidazoles

Substituted benzimidazoles and pyrimidazoles are an important group of heterocyclic aromatic organic compounds in the field of medicinal chemistry. A one-step microwave accelerated synthesis of substituted benzo- and pyridine-fused 1H-imidazoles has been described. Mechanistically, the reaction proceeds by reacting substituted 2-fluoronitrobenzene and substituted arylamine through the formation of N-hydroxy intermediate, which at higher temperature cleaves to afford the desired product. This approach achieved reductions in reaction times, higher yields, cleaner reactions than the previously described synthetic processes.