125572-33-0

Basic information

• Product Name: 1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridine
• Synonyms: 1H-Imidazo(4,5-b)pyridine, 1-methyl-6-phenyl-; 1-Methyl-6-phenyl-1H-imidazo(4,5-b)pyridine
• CAS NO: 125572-33-0
• Molecular Formula: C₁₃H₁₁N₃
• Molecular Weight: 209.2465
• Mol File: 125572-33-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 404.2°C at 760 mmHg
• Flash Point: 198.2°C
• Density: 1.19g/cm³
• Vapor Pressure: 9.62E-07mmHg at 25°C
• Refractive Index: 1.657
• CAS DataBase Reference: 1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridine(125572-33-0)
• EPA Substance Registry System: 1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridine(125572-33-0)

Safety Data

• Hazardous Substances Data: 125572-33-0(Hazardous Substances Data)

Upstream product

• 153434-55-0 1-Methyl-2-(methylthio)-6-phenylimidazo<4,5-b>pyridin-5(4H)-one 
• 166047-14-9 6-bromo-1-methylimidazo<4,5-b>pyridine 
• 98-80-6 phenylboronic acid 
• 79578-98-6 1-methyl-1H-imidazol-4-amine 
• 174814-20-1 3-methylthio-2-phenylacrolein 
• 64-18-6 formic acid 
• 107351-81-5 2-amino-3-methylamino-5-phenylpyridine 
• 944576-49-2 C₁₈H₂₀N₄O₂ 
• 452-58-4 2,3-Diaminopyridine 
• 199442-68-7 N-(2-Amino-pyridin-3-yl)-4-methyl-benzenesulfonamide 
• 199442-69-8 N-(2-Amino-pyridin-3-yl)-4,N-dimethyl-benzenesulfonamide 
• 199442-70-1 N-(2-Amino-5-iodo-pyridin-3-yl)-4,N-dimethyl-benzenesulfonamide 
• 7715-02-8 (2-methylsulfanylvinyl)benzene 
• 145083-27-8 4-Bromo-1-methyl-2-(methylthio)imidazole-5-carboxaldehyde 

Downstream Products

• 105650-23-5 2-amino-1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridine 
• 129018-59-3 2-nitro-1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridine 
• 944576-49-2 C₁₈H₂₀N₄O₂ 
• 124489-20-9 N-Hydroxy-PhIP 

Relevant articles and documents

Palladium(0)-catalyzed phenylation of imidazo[4,5-b]pyridines

The tetrakis(triphenylphosphine)palladium(0)-catalyzed coupling of benzeneboronic acid with 2-chloro, 6-bromo and 6-bromo-2-chloro derivatives of 1- and 3-methylimidazo[4,5-b]pyridines to novel 2-phenyl-, 6-phenyl- and 2,6-diphenylimidazo[4,5-b]pyridines is described. The phenylation of imidazo[4,5-b]pyridines containing labile hydrogens was not successful.

An easy photochemical approach to the synthesis of the food-borne carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine

Mutations induced by substances formed during food cooking are a field of growing interest; for a better comprehension of the mechanism of action of these carcinogens, simple routes to their synthesis are needed. In this letter we describe an easy method for 2-amino-1-methyl-6-phenylimidazo[4,5- b]pyridine (PhIP) synthesis, starling from the commercially available 2,3- diaminopyridine 1 via the 2-amino-3-methylamino-5-phenylpyridine 5 formation. The key step of this approach is the one pot synthesis of 5 performed by photolysis of 2-amino-5-iodo-3-(N-methyl-N-tosylamino)pyridine 4 to obtain simultaneous phenylation and tosyl group removal. Compound 5 was then used as an intermediate to obtain the 1-methyl 6-phenylimidazo[4,5-b]pylidine 6 which was aminated to afford PhIP in good overall yields.

Synthesis of Mutagenic Heterocyclic Amines PhIP and DMIP

-