274-47-5

Basic information

• Product Name: Imidazo[1,5-a]pyridine
• Synonyms: 2-Azaindolizine;Imidazolo[1,5-a]pyridine;Imidazo[1,5-a]pyridine
• CAS NO: 274-47-5
• Molecular Formula: C₇H₆N₂
• Molecular Weight: 118.14
• Mol File: 274-47-5.mol
• Article Data: 8

Chemical Properties

• Melting Point: 52.0 to 57.0 °C
• Boiling Point: 120-125 °C(Press: 3 Torr)
• Appearance: /
• Density: 1.14 g/cm³
• Refractive Index: 1.628
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 7.50±0.30(Predicted)
• CAS DataBase Reference: Imidazo[1,5-a]pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: Imidazo[1,5-a]pyridine(274-47-5)
• EPA Substance Registry System: Imidazo[1,5-a]pyridine(274-47-5)

Safety Data

• Hazardous Substances Data: 274-47-5(Hazardous Substances Data)

Usage

General Description

Imidazo[1,5-a]pyridine is a chemical compound belonging to the class of heterocyclic aromatic compounds. It is a fused heterobicyclic system containing an imidazole ring and a pyridine ring. Imidazo[1,5-a]pyridine is known for its bioactivity and is commonly used as a building block in the synthesis of various pharmaceuticals and agrochemicals. Its unique structural features make it a valuable scaffold for drug discovery and development, and it has been the subject of extensive research due to its potential pharmacological properties. The compound has shown promise in various areas, including cancer therapy, neurological disorders, and infectious diseases. Its versatility and pharmacological potential make Imidazo[1,5-a]pyridine a valuable and important chemical compound in medicinal chemistry and drug development.

InChI:InChI=1/C7H6N2/c1-2-4-9-6-8-5-7(9)3-1/h1-6H

Upstream product

• 3731-51-9 2-(Aminomethyl)pyridine 
• 64-18-6 formic acid 
• 75-52-5 nitromethane 
• 1121-60-4 pyridine-2-carbaldehyde 
• 50-00-0 formaldehyd 
• 56625-03-7 N-((pyridin-2-yl)methyl)formamide 
• 67-66-3 chloroform 

Downstream Products

• 1043871-89-1 3-[1-(1H-indol-3-yl)-but-3-enyl]-imidazo[1,5-a]pyridine 
• 1043871-90-4 1-[1-(1H-indol-3-yl)-but-3-enyl]-imidazo[1,5-a]pyridine 
• 1043871-91-5 1,3-bis-[1-(1H-indol-3-yl)-but-3-enyl]-imidazo[1,5-a]pyridine 
• 1060812-82-9 5-iodoimidazo[1,5-a]pyridine 

Relevant articles and documents

N-Heterocyclic carbenes derived from imidazo-[1,5-a]pyridines related to natural products: synthesis, structure and potential biological activity of some corresponding gold(I) and silver(I) complexes

A series of Au(I) complexes (12, 13, 14, 15, 16) and Ag(I) complexes (17, 18, 19, 20) derived from imidazo[1,5-a]pyridin-3-ylidenes were synthesized from AuCl(SMe2) or by reacting silver(I) acetate with 2,5-dimethylimidazo[1,5-a]pyridin-2-ium iodide or imidazo[1,5-a]pyridin-2-ium salts, and were characterized using NMR spectroscopy, mass spectrometry and elemental analyses. In addition, the Au(I) complex 13 and the Ag(I) complex 19 were characterized using single-crystal X-ray diffraction. Using paclitaxel as a standard, all Au(I) and Ag(I) N-heterocyclic carbene complexes were evaluated for their in vitro anti-tumour activity against 12 cell lines using a monolayer cell survival and proliferation assay. The highest anticancer activity was found for complexes 15, 13 and 14 with mean IC50 values of 10.09, 10.42 and 12.28?μM, respectively. Copyright

Synthesis of imidazo[1,5-a]pyridines via cyclocondensation of 2-(aminomethyl)pyridines with electrophilically activated nitroalkanes

Imidazo[1,5-a]pyridines were efficiently prepared via the cyclization of 2-picolylamines with nitroalkanes electrophilically activated in the presence of phosphorous acid in polyphosphoric acid (PPA) medium.

Formation of Imidazopyridines by the Phase Transfer Catalyzed Reaction of α-(Aminomethyl)pyridines with CHCl3 and Alkaline Hydroxide

The reaction of chloroform with 2-(aminomethyl)pyridine (1) under basic phase-transfer catalysis affords the highly fluorescent imidazopyridine (2) in 25percent isolated yield.Despite the formation of considerable tarry residue, GC-MS indicates that the volatile fraction of the reaction is simple and consists of 2 and two minor components identified as N-(2-pyridylmethyl)formamide (6) and (2-pyridylmethyl)isonitrile (7).The basic phase transfer catalyzed reaction of chloroform with a series of α-(aminomethyl)azanaphthalenes was found to be general and yield the corresponding annulated imidazo derivatives in comparable yields.Despite product yields in the 25percent range, GC of the reaction mixtures indicates that the volatile fractions generally consist of residual starting aminomethyl compound, the imidazo product, and a minor amount of the (α-azanaphthylmethyl)formamide.However, 3-(aminomethyl)isoquinoline (18) failed to provide any of the expected imidazoisoquinoline (19).The failure to detect 19 was investigated.