30384-94-2

Basic information

• Product Name: 7-METHYLIMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE
• Synonyms: 7-METHYLIMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE;CHEMMAKER CMFS-00378;IMidazo[1,2-a]pyridine-3-carboxaldehyde, 7-Methyl-
• CAS NO: 30384-94-2
• Molecular Formula: C₉H₈N₂O
• Molecular Weight: 160.17
• Mol File: 30384-94-2.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• Density: 1.211 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 4.79±0.50(Predicted)
• CAS DataBase Reference: 7-METHYLIMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-METHYLIMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE(30384-94-2)
• EPA Substance Registry System: 7-METHYLIMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE(30384-94-2)

Safety Data

• Hazardous Substances Data: 30384-94-2(Hazardous Substances Data)

Usage

General Description

7-Methylimidazo[1,2-a]pyridine-3-carbaldehyde is a chemical compound with a molecular structure containing a pyridine ring and an imidazole ring with a methyl group attached to the nitrogen atom. It is commonly used as a flavorant and fragrant in foods, beverages, and tobacco products. It is also known to be a potent mutagen and carcinogen, with studies linking it to various types of cancer, particularly in the digestive and respiratory systems. Due to its potential health risks, there are limitations and regulations on the use of 7-methylimidazo[1,2-a]pyridine-3-carbaldehyde in consumer products.

Upstream product

• 68-12-2 N,N-dimethyl-formamide 
• 874-39-5 7-Methyl-imidazo[1,2-a]pyridine 
• 695-34-1 2-Amino-4-methylpyridine 
• 1249030-09-8 4-methyl-N-(prop-2-ynyl)pyridine-2-amine 
• 624-67-9 Propargylic aldehyde 
• 67-68-5 dimethyl sulfoxide 
• 93-61-8 N-methyl-N-phenylformamide 
• 2065-75-0 2-Bromo-malonaldehyde 

Downstream Products

• 217304-43-3 7-Methyl-3-vinyl-imidazo[1,2-a]pyridine 
• 30493-10-8 7-Methyl-imidazo[1,2-a]pyridine-3-carbaldehyde oxime 

Relevant articles and documents

Microwave-assisted synthesis of 3-formyl substituted imidazo[1,2-a]pyridines

An efficient, metal-free method for the synthesis of 3-formyl imidazo[1,2-a]pyridines is reported. The method utilises commercially available substrates and features a broad substrate scope. The intermediate enamine was isolated and a plausible reaction mechanism proposed.

Identification of the Privileged Position in the Imidazo[1,2-a]pyridine Ring of Phosphonocarboxylates for Development of Rab Geranylgeranyl Transferase (RGGT) Inhibitors

Members of the Rab GTPase family are master regulators of vesicle trafficking. When disregulated, they are associated with a number of pathological states. The inhibition of RGGT, an enzyme responsible for post-translational geranylgeranylation of Rab GTPases represents one way to control the activity of these proteins. Because the number of molecules modulating RGGT is limited, we combined molecular modeling with biological assays to ascertain how modifications of phosphonocarboxylates, the first reported RGGT inhibitors, rationally improve understanding of their structure-activity relationship. We have identified the privileged position in the core scaffold of the imidazo[1,2-a]pyridine ring, which can be modified without compromising compounds' potency. Thus modified compounds are micromolar inhibitors of Rab11A prenylation, simultaneously being inactive against Rap1A/Rap1B modification, with the ability to inhibit proliferation of the HeLa cancer cell line. These findings were rationalized by molecular docking, which recognized interaction of phosphonic and carboxylic groups as decisive in phosphonocarboxylate localization in the RGGT binding site.

Aerobic iron(III)-catalyzed direct formylation of imidazo[1,2-a]pyridine using DMSO as carbon source

A novel and efficient iron(III)-catalyzed C3-formylation reaction of imidazo[1,2-a]pyridine in an oxygen atmosphere has been developed. The method is conducted in dimethyl sulfoxide (DMSO), which serves as both the carbonyl carbon source and solvent, in the presence of acetic acid to directly generate structurally diverse 3-formylimidazo[1,2-a]pyridine derivatives in moderate to good yields.