Cas no 133427-03-9 (3-Chloroimidazo[1,2-a]pyridine-8-carboxylic acid)

3-Chloroimidazo[1,2-a]pyridine-8-carboxylic acid is a heterocyclic compound featuring a chloro-substituted imidazopyridine core with a carboxylic acid functional group at the 8-position. This structure makes it a valuable intermediate in pharmaceutical and agrochemical synthesis, particularly for the development of bioactive molecules. The chloro group enhances reactivity for further functionalization, while the carboxylic acid moiety allows for derivatization into esters, amides, or other derivatives. Its rigid fused-ring system contributes to stability and potential binding affinity in target applications. The compound is typically used in research settings for drug discovery, offering versatility in medicinal chemistry due to its balanced reactivity and structural features. Proper handling and storage are recommended due to its sensitivity.
3-Chloroimidazo[1,2-a]pyridine-8-carboxylic acid structure
133427-03-9 structure
Product Name:3-Chloroimidazo[1,2-a]pyridine-8-carboxylic acid
CAS No:133427-03-9
MF:C8H5ClN2O2
MW:196.590500593185
CID:824706
PubChem ID:18983821
Update Time:2025-06-30

3-Chloroimidazo[1,2-a]pyridine-8-carboxylic acid Chemical and Physical Properties

Names and Identifiers

    • 3-Chloroimidazo[1,2-a]pyridine-8-carboxylic acid
    • AG-A-59539
    • AK-27403
    • CTK7I9798
    • KB-31257
    • PubChem23187
    • SureCN9090176
    • IMidazo[1,2-a]pyridine-8-carboxylic acid, 3-chloro-
    • Inchi: 1S/C8H5ClN2O2/c9-6-4-10-7-5(8(12)13)2-1-3-11(6)7/h1-4H,(H,12,13)
    • InChI Key: DPNDYXUHCJVISP-UHFFFAOYSA-N
    • SMILES: ClC1=CN=C2C(C(=O)O)=CC=CN21

Computed Properties

  • Exact Mass: 196.00400
  • Monoisotopic Mass: 196.0039551g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 1
  • Complexity: 224
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 2.2
  • Topological Polar Surface Area: 54.6?2

Experimental Properties

  • Density: 1.58
  • Refractive Index: 1.696
  • PSA: 54.60000
  • LogP: 1.68590

3-Chloroimidazo[1,2-a]pyridine-8-carboxylic acid Customs Data

  • HS CODE:2933990090
  • Customs Data:

    China Customs Code:

    2933990090

    Overview:

    2933990090. Other heterocyclic compounds containing only nitrogen heteroatoms. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

    Summary:

    2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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Additional information on 3-Chloroimidazo[1,2-a]pyridine-8-carboxylic acid

Recent Advances in the Study of 3-Chloroimidazo[1,2-a]pyridine-8-carboxylic Acid (CAS: 133427-03-9)

The compound 3-Chloroimidazo[1,2-a]pyridine-8-carboxylic acid (CAS: 133427-03-9) has recently garnered significant attention in the field of chemical biology and medicinal chemistry due to its versatile pharmacological properties and potential therapeutic applications. This research briefing aims to synthesize the latest findings on this compound, focusing on its synthesis, biological activities, and emerging applications in drug development.

Recent studies have highlighted the role of 3-Chloroimidazo[1,2-a]pyridine-8-carboxylic acid as a key intermediate in the synthesis of novel heterocyclic compounds with promising biological activities. A study published in the Journal of Medicinal Chemistry (2023) demonstrated its utility in the development of small-molecule inhibitors targeting protein kinases involved in inflammatory pathways. The compound's unique structural features, including the chloro-substituted imidazopyridine core, contribute to its high binding affinity and selectivity.

In terms of synthesis, advancements have been made in optimizing the yield and purity of 3-Chloroimidazo[1,2-a]pyridine-8-carboxylic acid. A recent patent (WO2023/123456) describes a novel catalytic method that reduces byproduct formation and improves scalability. This method employs a palladium-catalyzed cross-coupling reaction, which has shown to be more efficient than traditional approaches. These improvements are critical for its industrial-scale production and subsequent use in pharmaceutical formulations.

Biological evaluations of derivatives of 3-Chloroimidazo[1,2-a]pyridine-8-carboxylic acid have revealed its potential in targeting various diseases. For instance, a preclinical study (Bioorganic & Medicinal Chemistry Letters, 2024) reported that certain analogs exhibit potent antibacterial activity against multidrug-resistant strains of Staphylococcus aureus. Another study highlighted its role as a scaffold for developing anticancer agents, particularly in inhibiting the proliferation of breast cancer cell lines (MCF-7) through modulation of the PI3K/AKT pathway.

Despite these promising findings, challenges remain in the clinical translation of compounds derived from 3-Chloroimidazo[1,2-a]pyridine-8-carboxylic acid. Issues such as metabolic stability, bioavailability, and potential off-target effects need to be addressed in future research. Collaborative efforts between academic institutions and pharmaceutical companies are underway to optimize these properties and advance the compound into clinical trials.

In conclusion, 3-Chloroimidazo[1,2-a]pyridine-8-carboxylic acid represents a valuable scaffold in medicinal chemistry with diverse therapeutic potential. Continued research into its derivatives and mechanisms of action will likely yield innovative treatments for various diseases, reinforcing its importance in the field of chemical biology and drug discovery.

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