105942-43-6

Basic information

• Product Name: 1-Benzyl-1H-imidazo[4,5-b]pyridine
• Synonyms: 1-Benzyl-1H-imidazo[4,5-b]pyridine
• CAS NO: 105942-43-6
• Molecular Formula: C₁₃H₁₁N₃
• Molecular Weight: 209.251
• Mol File: 105942-43-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 402.653°C at 760 mmHg
• Flash Point: 197.318°C
• Appearance: /
• Density: 1.185g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.656
• Storage Temp.: 2-8°C
• PKA: 5.24±0.30(Predicted)
• CAS DataBase Reference: 1-Benzyl-1H-imidazo[4,5-b]pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Benzyl-1H-imidazo[4,5-b]pyridine(105942-43-6)
• EPA Substance Registry System: 1-Benzyl-1H-imidazo[4,5-b]pyridine(105942-43-6)

Safety Data

• Hazardous Substances Data: 105942-43-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 960, 1995 DOI: 10.1021/jo00109a029

InChI:InChI=1/C13H11N3/c1-2-5-11(6-3-1)9-16-10-15-13-12(16)7-4-8-14-13/h1-8,10H,9H2

Upstream product

• 105942-39-0 4-(Phenylmethyl)-4H-imidazo<4,5-b>pyridine 
• 100-46-9 benzylamine 
• 64-18-6 formic acid 
• 79707-12-3 2-amino-3-<(phenylmethyl)amino>pyridine 
• 54231-40-2 2-nitro-3-benzylaminopyridine 
• 54231-35-5 3-fuoro-2-nitropyridine 
• 77287-34-4 formamide 
• 142670-87-9 N-benzyl-N-(2-chloro-3-pyridinyl)amine 
• 100-52-7 benzaldehyde 
• 386275-19-0 benzylidene(2-chloropyridin-3-yl)amine 
• 6298-19-7 2-chloro-3-aminopyridine 
• 122-51-0 orthoformic acid triethyl ester 
• 158525-50-9 N-(3-amino-2-pyridinyl)-formamide 
• 273-21-2 1H-Imidazo[4,5-b]pyridine 

Downstream Products

• 1334165-46-6 1-benzyl-2-iodo-4-azabenzimidazole 
• 1334165-48-8 2,2'-bis(1-benzyl-2-iodo-4-azabenzimidazole) 
• 1334165-53-5 1-benzyl-3-(2-oxopropyl)-4-azabenzimidazolium chloride 
• 1384975-20-5 (E)-N-(2-{[5-amino-2,2-dimethyl-3(2H)-furanyliden]amino}-3-pyridinyl)-N-benzylformamide 
• 1384975-15-8 (Z)-2-[9-benzyl-2,2-dimethyl-9,9a-dihydro[1,3]oxazolo[2',3':2,3]imidazo[4,5-b]pyridin-3(2H)-yliden]acetonitrile 
• 1431659-81-2 4-(1-benzyl-1H-imidazo[4,5-b]pyridine-2-yl)morpholine 
• 1431659-62-9 1-benzyl-2-chloro-1H-imidazo[4,5-b]pyridine 

Relevant articles and documents

Palladium-Catalyzed Suzuki Cross-Coupling of 2-Halo-Deazapurines with Potassium Organotrifluoroborate Salts in the Regioselective Synthesis of Imidazo[4,5-b]pyridine Analogues

In this paper, we report the use of potassium organotrifluoroborate salts as nucleophilic organoboron reagents in the Suzuki cross-coupling reactions of 2-halo deazapurines. Regio-isomeric C-2-substituted imidazo[4,5-b]pyridine analogues were synthesized by employing this protocol in good to excellent yields. Whereas aryl and heteroaryl trifluoroborates reacted readily to give the coupled products in high yields, alkyltrifluoroborates were found to be less reactive. The utilization of tetrabutylammonium acetate was found to play a substantial role in enhancing the reaction rates of the cross-coupling process. Also, a comparative study was performed between boronic acids and potassium organotrifluoroborate salts.

An improved synthesis of imidazo[4,5-b]pyridines and imidazo[4,5-b]pyrazines by palladium catalyzed amidation using xantphos in a 1,4-dioxane:tert-amyl alcohol solvent system

Herein an improved protocol for the synthesis of imidazo[4,5-b]pyridines and imidazo[4,5-b]pyrazines using a palladium-catalyzed amidation that utilizes Xantphos as an ancillary phosphine ligand is reported. The use of a binary solvent system comprised of

Facile, regioselective syntheses of N-alkylated 2,3-diaminopyridines and imidazo[4,5-b]pyridines

Useful strategies are reported for the differentiation and selective synthetic manipulations of amino groups at the 2- and 3-positions of pyridines. It has been found that 2,3-diaminopyridine reacts with aldehydes under reductive amination conditions to g