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

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

Uses

Used in Flavor and Fragrance Industry:
7-METHYLIMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE is used as a flavorant and fragrant in the food, beverage, and tobacco products industries due to its ability to impart specific taste and aroma profiles. Its use in these applications is regulated to mitigate potential health risks associated with its mutagenicity and carcinogenicity.
Used in Chemical Research:
In the field of chemical research, 7-METHYLIMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE serves as a starting material or intermediate in the synthesis of various organic compounds, including pharmaceuticals and agrochemicals. Its unique molecular structure allows for the development of new compounds with potential therapeutic or functional properties.

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.

Heterogeneous gold(I)-catalysed annulation between 2-aminopyridines and propiolaldehydes leading to 3-acylimidazo[1,2-a]pyridines

The heterogeneous annulation between 2-aminopyridines and propiolaldehydes was achieved in CH2Cl2 at 25 °C in the presence of 3 mol% of MCM-41-immobilised phosphine gold(I) complex (MCM-41-PPh3-AuCl) and AgSbF6

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.

A formyl Heteraromatic hydrocarbons the synthetic method of the compound of pharmaceutical intermediates

The invention relates to a method for synthesizing a formyl heterocyclic aromatic drug intermediate compound shown as a formula (I) in the specification. The method comprises the following step: enabling a compound of a formula (II) in the specification to react with a compound of a formula (III) in the specification in an organic solvent in the presence of a catalyst, an oxidant and reaction aids, thereby obtaining the compound of the formula (I), wherein R1, R2, R3 and R4 are respectively and independently selected from H, C1-C6 alkyl, C1-C6 alkoxy, phenyl or nitro. According to the method, the catalyst, oxidant, reaction aids and reaction substrate are selected and combined, so that formylation at a specific site is realized, and the method has high yield and has wide application prospects and potentials in the field of synthetic methods of drug intermediates.

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.

Cu-Catalyzed selective C3-formylation of imidazo[1,2-a]pyridine C-H bonds with DMSO using molecular oxygen

Using the widely available DMSO as the formylation reagent under oxidative conditions, an efficient Cu-catalyzed C3-formylation reaction of imidazo[1,2-a]pyridine C-H bonds to directly generate structurally sophisticated 3-formyl imidazo[1,2-a]pyridine derivatives has been developed. The reaction proceeded to generate products in good yields, and used the environmentally friendly molecular oxygen as the oxidant.

Transition metal-mediated C=O and C=C bond-forming reactions: A regioselective strategy for the synthesis of imidazo[1,2- A ]pyridines and imidazo[1,2- A ]pyrazines

A novel and convenient transformation for the regiospecific synthesis of functionalized imidazo[1,2-a]pyridine aldehydes/ketones and 3-vinyl imidazo[1,2-a]pyridines has been developed via copper(I)- and palladium(II)-catalyzed cyclization. The one-pot reaction proceeds smoothly with commercially available catalysts and affords the products in moderate to good yields. It represents an efficient approach for the formation of C-N, C=O, and C=C bonds under mild conditions.

Synthesis of imidazo[1,2-a]pyridines: "Water-mediated" hydroamination and silver-catalyzed aminooxygenation

Aqueous syntheses of methylimidazo[1,2-a]pyridines without any deliberate addition of catalyst are reported. Imidazo[1,2-a]pyrazine and imidazo[2,1-a]isoquinoline were also obtained in good yields under similar conditions. With acetonitrile as solvent, Ag

Synthesis of acyclo-C-nucleosides in the imidazo[1,2-a]pyridine and pyrimidine series as antiviral agents

The synthesis and the antiviral activities of C-3 acyclic nucleoside analogues of imidazo[1,2-a]pyridine and pyrimidine are reported. From these compounds, 20, 21, 22, 23, 28, and 34 showed a specific activity against cytomegalovirus and/or varicella-zoster virus.