29096-59-1

Basic information

• Product Name: 6-CHLOROIMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE
• Synonyms: 6-CHLOROIMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE;CHEMMAKER CMFS-00375;IMidazo[1,2-a]pyridine-3-carboxaldehyde, 6-chloro-
• CAS NO: 29096-59-1
• Molecular Formula: C₈H₅ClN₂O
• Molecular Weight: 180.6
• Product Categories: Heterocycle-Pyridine series
• Mol File: 29096-59-1.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Density: 1.429 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 6-CHLOROIMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CHLOROIMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE(29096-59-1)
• EPA Substance Registry System: 6-CHLOROIMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE(29096-59-1)

Safety Data

• Hazardous Substances Data: 29096-59-1(Hazardous Substances Data)

Usage

General Description

6-Chloroimidazo[1,2-a]pyridine-3-carbaldehyde is a chemical compound with the molecular formula C8H5ClN2O. It is a heterocyclic compound containing an imidazo[1,2-a]pyridine ring system with a chlorine atom and a formyl group attached at the 3-position. 6-CHLOROIMIDAZO[1,2-A]PYRIDINE-3-CARBALDEHYDE is a versatile building block for the synthesis of various pharmaceuticals, agrochemicals, and functional materials. It can undergo different chemical reactions, such as cross-coupling, cycloaddition, and substitution reactions, to form a wide range of derivatives with diverse properties and applications. Its unique structure and reactivity make it an important intermediate in organic synthesis and medicinal chemistry.

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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.

Copper-catalyzed intramolecular dehydrogenative aminooxygenation: Direct access to formyl-substituted aromatic N-heterocycles

A direct synthesis of carbaldehydes through intramolecular dehydrogenative aminooxygenation has been developed. The process uses a catalytic amount of copper(II) in DMF or DMA under oxygen and does not require additional oxidants (see scheme). Mechanistic studies suggest that the carbonyl oxygen atom of the aldehyde is derived from oxygen through a copper-mediated oxygen activation process via a peroxy-copper(III) intermediate. Copyright