5857-47-6

Usage

Uses

Used in Research and Development:
3-bromo-5-methylimidazo[1,2-a]pyridine is used as a research compound for studying its mutagenicity and carcinogenic properties. It helps scientists understand the mechanisms of its formation in cooked foods and its potential health effects, particularly its association with an increased risk of certain types of cancer.
Used in Food Safety and Quality Control:
3-bromo-5-methylimidazo[1,2-a]pyridine is used as an indicator in food safety and quality control processes. Monitoring its levels in cooked meat and fish products can help ensure that they meet safety standards and reduce the risk of potential health effects for consumers.
Used in Public Health and Nutrition Education:
3-bromo-5-methylimidazo[1,2-a]pyridine is used as a reference compound in public health and nutrition education to raise awareness about the potential risks associated with consuming high levels of cooked meat and fish. Educating consumers about the importance of limiting their intake of these foods can help reduce the risk of certain types of cancer and promote overall health.

Upstream product

• 933-69-7 5-methylimidazo[1,2-a]pyridine 
• 1824-81-3 2-Amino-6-methylpyridine 

Relevant academic research and scientific papers

Reactions with N-chlorosuccinimide of various 5-methylimidazo[1,2-a]pyridine derivatives with an electron-withdrawing group substituted at the 3-position

Chlorination reactions using N-chlorosuccinimide (NCS) was investigated for various 5-methylimidazo[1,2-a]pyridine derivatives with an electron-withdrawing group substituted at the 3-position. These reactions showed different results, and by examining these, we proposed a reaction mechanism via the appropriate 3-halogenoimidazo[1,2-a]pyridium compounds as the reaction intermediates.

Reaction of 3-Substituted Imidazopyridines with Br+ and the Alleged 5-Bromo-Substituted Product

The reaction of 3-methylimidazopyridine with NBS was reinvestigated and is shown to give products formed by apparent nucleophilic substitution at the 2-position.NBS in CHCl3 gave compounds 4 and 6, while NBS in CCl4 or Br2 in CHCl3 gave exclusively 4.Mechanisms and differences in product formation are discussed; evidence that the previously reported NBS product was in fact 3-bromo-5-methylimidazopyridine, rather than the alleged 5-bromo-3-methyl derivative 3, is presented.Compound 3 was prepared by diazotization of 5-amino-3-methylimidazopyridine in the presence of HBr and by condensation of 2-bromopropanal (or its acetal) with 2-amino-6-bromopyridine (12).This latter reaction of the weakly basic aminopyridine 12 is shown to follow the normal pattern in which the amino nitrogen condenses with the carbonyl carbon.Structures are established by infrared, mass, and 1H-NMR spectral analyses, mechanistic considerations, and diagnostic reactions.Experimental and computer-generated 1H-NMR spectra of compounds 3 and 13 are reproduced.