6558-63-0

Basic information

• Product Name: 3-METHYLIMIDAZO[1,5-A]PYRIDINE
• Synonyms: 3-METHYLIMIDAZO[1,5-A]PYRIDINE
• CAS NO: 6558-63-0
• Molecular Formula: C₈H₈N₂
• Molecular Weight: 132.16252
• Mol File: 6558-63-0.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-METHYLIMIDAZO[1,5-A]PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYLIMIDAZO[1,5-A]PYRIDINE(6558-63-0)
• EPA Substance Registry System: 3-METHYLIMIDAZO[1,5-A]PYRIDINE(6558-63-0)

Safety Data

• Hazardous Substances Data: 6558-63-0(Hazardous Substances Data)

Usage

General Description

3-Methylimidazo[1,5-a]pyridine, also known as MIP, is a heterocyclic aromatic amine that is formed during the cooking process of meat and fish at high temperatures. It is classified as a potential human carcinogen by the International Agency for Research on Cancer. MIP is also found in cigarette smoke and has been identified as a mutagen, meaning it has the ability to cause changes in the genetic material of cells, potentially leading to cancer. Due to its carcinogenic properties, there is growing concern about human exposure to MIP through the consumption of cooked meats and fish, as well as through tobacco smoke. Efforts are being made to reduce the levels of MIP in food and to better understand its health effects.

Upstream product

• 58481-18-8 N-(pyridin-2-ylmethyl)acetamide 
• 122083-00-5 N-<(2-pyridyl)methyl>thioacetamide 
• 3731-51-9 2-(Aminomethyl)pyridine 
• 108-24-7 acetic anhydride 
• 21478-42-2 2-methyl-N-(pyridin-2-ylmethylene)propan-2-amine 
• 274-59-9 triazolopyridine 
• 75-05-8 acetonitrile 
• 1121-60-4 pyridine-2-carbaldehyde 
• 75-04-7 ethylamine 
• 407-25-0 trifluoroacetic anhydride 
• 79-24-3 Nitroethane 

Downstream Products

• 10350-68-2 2-(5-methyl-1,2,4-oxadiazol-3-yl)pyridine 
• 610276-97-6 3-methylimidazo[1,5-a]pyridine-1-carbaldehyde 
• 61254-44-2 3-bromo-1-methylimidazo[1,5-a]pyridine 
• 72315-48-1 3-methyl-1-nitro-imidazo[1,5-a]pyridine 

Relevant articles and documents

Imidazopyridinium cations: A new family of azonia aromatic heterocycles with applications as DNA intercalators

Two novel imidazopyridinium cations formed by a hexacyclic azonia aromatic system have been synthesized. Spectrofluorimetric titrations, circular dichroism measurements, theoretical simulations and fluorescence-based thermal denaturation experiments on these materials have shown the interesting fluorescence properties and DNA-binding ability by intercalation, with a marked preference for AT-rich sequences. Compound 2 presents the highest fluorescence quantum yield (0.32 in 5% DMSO/water and 0.46 in MeOH) and affinity for DNA (binding constant of ～4.5 × 105 M?1). Moreover, the potential of these compounds for cell staining has been investigated in living HeLa cells by confocal microscopy imaging. This analysis showed the remarkable capacity of both compounds for uptake and accumulation by living cells.

Thionyl chloride-mediated synthesis of 2-azaindolizine sulfur-bridged dimers by C-H bond direct chalcogenation of imidazo[1,5-a]pyridines

Thionyl chloride-mediated chalcogenation of imidazo[1,5-a]pyridine serves as a new protocol for the synthesis of rare bisimidazopyridyl sulfides. This method provides the new route to synthesis of 2-azaindolizine sulfur-bridged dimers called chalcogenide

Novel one-pot synthesis of dihydroacenaphtho[1,2-f][1,3]-oxazepines via 1,4-dipolar cycloaddition reaction

A facile three-component reaction involving 3-alkyl(aryl)imidazo[1,5-a]pyridines 7a-g, dimethyl acetylenedicarboxylate 2 (DMAD) and acenaphthene-1,2-dione 5 led to the construction of the respective dihydroacenaphtho[1,2-f][1,3]oxazepine-10,11-dicarboxylates 10a-g in fair yields. Structures of the latter tetracyclic adducts, are based on NMR and MS spectral data and confirmed by single-crystal X-ray diffraction analysis for compound 10a. Most logically, the reaction proceeds via initial formation of the relevant diastereomeric spiro[1,3]oxazine-1,4-dipolar cycloadducts 12, 13 which then suffer skeletal rearrangement leading to the respective acenaphtho[1,2-f][1,3]oxazepines 10a-g.