6188-43-8

Basic information

• Product Name: IMIDAZO[1,2-A]PYRIDIN-3-CARBOXALDEHYDE
• Synonyms: IMIDAZO[1,2-A]PYRIDINE-3-CARBOXALDEHYDE;IMIDAZO[1,2-A]PYRIDIN-3-CARBOXALDEHYDE;Imidazo[1,2-a]pyridine-3-carbaldehyde;[1,2-α]PYRIDIN-3-CARBOXALDEHYDE;Imidazo[1,2-a]pyridine-3-carbaldehyde AldrichCPR;3-imidazo[3,2-a]pyridinecarboxaldehyde;imidazo[3,2-a]pyridine-3-carbaldehyde
• CAS NO: 6188-43-8
• Molecular Formula: C₈H₆N₂O
• Molecular Weight: 146.15
• Product Categories: blocks;Imidazoles;Pyridines
• Mol File: 6188-43-8.mol
• Article Data: 26

Chemical Properties

• Melting Point: 127-129 °C
• Appearance: /
• Density: 1.25 g/cm³
• Refractive Index: 1.641
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 4.15±0.50(Predicted)
• CAS DataBase Reference: IMIDAZO[1,2-A]PYRIDIN-3-CARBOXALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: IMIDAZO[1,2-A]PYRIDIN-3-CARBOXALDEHYDE(6188-43-8)
• EPA Substance Registry System: IMIDAZO[1,2-A]PYRIDIN-3-CARBOXALDEHYDE(6188-43-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• HazardClass: IRRITANT
• Hazardous Substances Data: 6188-43-8(Hazardous Substances Data)

Usage

General Description

IMIDAZO[1,2-A]PYRIDIN-3-CARBOXALDEHYDE, also known as 3-formylimidazo[1,2-a]pyridine, is a chemical compound with the molecular formula C8H6N2O. It is a heterocyclic compound with a fused imidazo-pyridine ring system and an aldehyde group. IMIDAZO[1,2-A]PYRIDIN-3-CARBOXALDEHYDE has been identified as a key intermediate in the synthesis of pharmaceuticals and agrochemicals, as well as a building block for the preparation of various heterocyclic compounds. It has also been studied for its potential biological activities and pharmacological properties. Its aromatic and heterocyclic properties make it an important compound in the field of organic chemistry and drug discovery.

InChI:InChI=1/C8H6N2O/c11-6-7-5-9-8-3-1-2-4-10(7)8/h1-6H

Upstream product

• 74944-12-0 2,2,2-Trichloro-1-imidazo[1,2-a]pyridin-3-yl-ethanol 
• 504-29-0 2-aminopyridine 
• 274-76-0 imidazo[1,2-a]pyridine 
• 2717-95-5 1-(imidazo[1,2-a]pyridin-3-yl)-N,N-dimethylmethanamine 
• 2065-75-0 2-Bromo-malonaldehyde 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 
• 67-68-5 dimethyl sulfoxide 
• 624-67-9 Propargylic aldehyde 
• 5857-45-4 3-methylimidazo[1,2-α]pyridine 
• 117459-95-7 N-(prop-2-yn-1-yl)pyridin-2-amine 
• 5866-28-4 2-(prop-2-enylamino)pyridine 
• 38427-94-0 N-(tert-butoxycarbonyl)-2-aminopyridine 
• 1284210-49-6 tert-butyl prop-2-yn-1-yl(pyridin-2-yl)carbamate 
• 63247-73-4 3-triethylgermyl-2-propyn-1-ol 

Downstream Products

• 219310-71-1 benzyl (E)-3-(imidazo<1,2-a>pyridin-3-yl)acrylate 
• 30493-06-2 2-(4-chlorophenyl)imidazo[1,2-a]pyridine-3-carbaldehyde 
• 30489-48-6 (2-(4-chlorophenyl)imidazo [1,2-a] pyridin-3-yl)methanol 
• 103845-12-1 N-((2-(4-chlorophenyl)imidazo[1,2-a]pyridine-3-yl)methyl)butyramide 
• 103844-86-6 N-((2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)-N-methylbutyramide 
• 1427161-67-8 imidazo[1,2-a]pyridine-3-carbaldehyde[4-(2-hydroxy-5-methoxyphenyl)-1,3-thiazol-2-yl]-hydrazone 
• 400037-31-2 (E)-ethyl 3-(imidazo[1,2-a]pyridin-3-yl)acrylate 
• 1396722-13-6 (E)-tert-butyl (2-(3-(imidazo[1,2-a]pyridin-3-yl)acrylamido)phenyl)carbamate 
• 113855-44-0 3-chloromethylimidazo[1,2-a]pyridine 
• 188395-46-2 ethyl α-[(triphenylphosphoranylidene)amino]-β-(imidazo[1,2-a]pyridin-3-yl)propenoate 
• 936134-17-7 N-(cyclohexylcarbamoyl-imidazo[1,2-a]pyridin-3-yl-methyl)-2-fluoro-N-(4-methoxy-benzyl)-5-nitro-benzamide 
• 30489-43-1 3-hydroxymethylimidazo[1,2-a]pyridine 

Relevant articles and documents

Synthesis, chiral high performance liquid chromatographic resolution and enantiospecific activity of a potent new geranylgeranyl transferase inhibitor, 2-hydroxy-3-imidazo[1,2-a]pyridin-3-yl-2-phosphonopropionic Acid

3-(3-Pyridyl)-2-hydroxy-2-phosphonopropanoic acid (3-PEHPC, 1) is a phosphonocarboxylate (PC) analogue of 2-(3-pyridyl)-1- hydroxyethylidenebis(phosphonic acid) (risedronic acid, 2), an osteoporosis drug that decreases bone resorption by inhibiting farnesyl pyrophosphate synthase (FPPS) in osteoclasts, preventing protein prenylation. 1 has lower bone affinity than 2 and weakly inhibits Rab geranylgeranyl transferase (RGGT), selectively preventing prenylation of Rab GTPases. We report here the synthesis and biological studies of 2-hydroxy-3-imidazo[1,2-a]pyridin-3-yl-2- phosphonopropionic acid (3-IPEHPC, 3), the PC analogue of minodronic acid 4. Like 1, 3 selectively inhibited Rab11 vs. Rap 1A prenylation in J774 cells, and decreased cell viability, but was 33-60 × more active in these assays. After resolving 3 by chiral HPLC (>98% ee), we found that (+)-3-E1 was much more potent than (-)-3-E2 in an isolated RGGT inhibition assay, ～17 × more potent (LED 3 μM) than (-)-3-E2 in inhibiting Rab prenylation in J774 cells and >26× more active in the cell viability assay. The enantiomers of 1 exhibited a 4-fold or smaller potency difference in the RGGT and prenylation inhibition assays.

Iodine-mediated aminohalogenation-oxidation to synthesize 2-fluoroalkyl imidazole derivatives

A simple and efficient method of iodine-mediated aminohalogenation-oxidation of fluorinated N’-propargyl amidines to synthesize 2-fluoroalkyl imidazole-5-carbaldehydes was developed. This method showed good functional group compatibility and wide substrat

Novel method for constructing imidazolyl[1,2-a]pyridyl-3-aldehyde by taking DMF as formylation reagent

The invention discloses a novel method for constructing imidazolyl[1,2-a]pyridyl-3-aldehyde in one step by taking DMF (N,N-dimethylformamide) as a formylation reagent. According to the method, imidazolyl[1,2-a]pyridine serves as a reactant, and the imidazolyl[1,2-a]pyridyl-3-aldehyde is constructed in one step by taking the DMF (N,N-dimethylformamide) as the formylation reagent. According to the method disclosed by the invention, the means of synthesis is novel, the reaction conditions are mild, the reaction reagent is cheap and readily available, the N,N-dimethylformamide can serve as a reaction solvent and also can serve as a formylation reagent, and thus, the method is in line with development requirements of green chemistry.

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.