Cas no 896139-85-8 (Imidazo[1,2-a]pyridin-7-ol)

Imidazo[1,2-a]pyridin-7-ol is a heterocyclic compound featuring a fused imidazole and pyridine core with a hydroxyl substituent at the 7-position. This structure imparts unique electronic and steric properties, making it a valuable intermediate in pharmaceutical and agrochemical synthesis. Its rigid bicyclic framework enhances binding affinity in medicinal chemistry applications, particularly in the development of kinase inhibitors and antimicrobial agents. The hydroxyl group offers a versatile handle for further functionalization, enabling derivatization via etherification, esterification, or metal-catalyzed cross-coupling reactions. High purity grades ensure reproducibility in research and industrial processes. The compound’s stability under standard conditions facilitates handling and storage.
Imidazo[1,2-a]pyridin-7-ol structure
Imidazo[1,2-a]pyridin-7-ol structure
Product Name:Imidazo[1,2-a]pyridin-7-ol
CAS No:896139-85-8
MF:C7H6N2O
MW:134.13534116745
MDL:MFCD13176749
CID:714885
PubChem ID:27973887
Update Time:2025-05-25

Imidazo[1,2-a]pyridin-7-ol Chemical and Physical Properties

Names and Identifiers

    • Imidazo[1,2-a]pyridin-7-ol
    • 1H-imidazo[1,2-a]pyridin-7-one
    • 7-Hydroxyimidazo[1,2-a]pyridine
    • AK104038
    • BCP13666
    • Imidazo[1,2-a]pyridin-7(1H)-one
    • 4845AC
    • FCH1161414
    • OR305451
    • ST2419420
    • AX8235577
    • DTXSID20650763
    • F17865
    • MFCD13176749
    • DS-4210
    • AKOS016006181
    • 896139-85-8
    • SCHEMBL21591074
    • SY114662
    • Imidazo[1 pound not2-a]pyridin-7-ol
    • EN300-305756
    • DB-108985
    • SCHEMBL601353
    • MDL: MFCD13176749
    • Inchi: 1S/C7H6N2O/c10-6-1-3-9-4-2-8-7(9)5-6/h1-5,10H
    • InChI Key: VIDSNQQGYGJWOU-UHFFFAOYSA-N
    • SMILES: OC1=CC2N(C=CN=2)C=C1

Computed Properties

  • Exact Mass: 134.04800
  • Monoisotopic Mass: 134.048012819g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 0
  • Complexity: 263
  • 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
  • Topological Polar Surface Area: 32.299
  • Surface Charge: 0
  • Tautomer Count: 3
  • XLogP3: 0.2

Experimental Properties

  • Color/Form: No data avaiable
  • Density: 1.33±0.1 g/cm3 (20 oC 760 Torr)
  • Melting Point: No data available
  • Boiling Point: No data available
  • Flash Point: No data available
  • Refractive Index: 1.668
  • PSA: 37.53000
  • LogP: 1.03990
  • Vapor Pressure: No data available

Imidazo[1,2-a]pyridin-7-ol Security Information

Imidazo[1,2-a]pyridin-7-ol 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%

Imidazo[1,2-a]pyridin-7-ol Pricemore >>

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Imidazo[1,2-a]pyridin-7-ol Production Method

Production Method 1

Reaction Conditions
1.1 Solvents: Ethanol ,  Water ;  overnight, reflux
Reference
Structure-based design and synthesis of imidazo[1,2-a]pyridine derivatives as novel and potent Nek2 inhibitors with in vitro and in vivo antitumor activities
Xi, Jian-Bei; Fang, Yan-Fen; Frett, Brendan; Zhu, Meng-Li; Zhu, Tong; et al, European Journal of Medicinal Chemistry, 2017, 126, 1083-1106

Production Method 2

Reaction Conditions
1.1 Reagents: Lithium hydroxide Catalysts: Copper(II) acetylacetonate ,  N1,N2-Bis(4-hydroxy-2,6-dimethylphenyl)ethanediamide ;  rt
1.2 Solvents: Dimethyl sulfoxide ,  Water ;  24 h, 80 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ;  acidified, cooled
Reference
Copper-Catalyzed Hydroxylation of (Hetero)aryl Halides under Mild Conditions
Xia, Shanghua; Gan, Lu; Wang, Kailiang; Li, Zheng; Ma, Dawei, Journal of the American Chemical Society, 2016, 138(41), 13493-13496

Imidazo[1,2-a]pyridin-7-ol Raw materials

Imidazo[1,2-a]pyridin-7-ol Preparation Products

Additional information on Imidazo[1,2-a]pyridin-7-ol

Recent Advances in the Study of Imidazo[1,2-a]pyridin-7-ol (CAS: 896139-85-8) in Chemical Biology and Pharmaceutical Research

The compound Imidazo[1,2-a]pyridin-7-ol (CAS: 896139-85-8) has recently garnered significant attention in the field of chemical biology and pharmaceutical research due to its versatile pharmacological properties and potential therapeutic applications. This heterocyclic scaffold is a key structural motif in various bioactive molecules, exhibiting a broad spectrum of biological activities, including antimicrobial, anticancer, and anti-inflammatory effects. Recent studies have focused on elucidating its mechanism of action, optimizing its synthetic pathways, and exploring its potential as a lead compound for drug development.

One of the most notable advancements in this area is the discovery of Imidazo[1,2-a]pyridin-7-ol derivatives as potent inhibitors of specific kinase targets involved in cancer progression. A 2023 study published in the Journal of Medicinal Chemistry demonstrated that certain derivatives of this compound exhibit high selectivity and efficacy against tyrosine kinase receptors, which are often overexpressed in various malignancies. The study utilized molecular docking and in vitro assays to validate the binding affinity and inhibitory effects of these derivatives, paving the way for further preclinical evaluations.

In addition to its anticancer potential, Imidazo[1,2-a]pyridin-7-ol has also been investigated for its role in modulating inflammatory pathways. A recent publication in Bioorganic & Medicinal Chemistry Letters highlighted its ability to suppress the production of pro-inflammatory cytokines by targeting key signaling molecules such as NF-κB and MAPK. These findings suggest that this compound could serve as a promising candidate for the development of novel anti-inflammatory therapeutics, particularly for chronic inflammatory conditions like rheumatoid arthritis and inflammatory bowel disease.

From a synthetic chemistry perspective, researchers have made significant strides in optimizing the production of Imidazo[1,2-a]pyridin-7-ol and its derivatives. A 2022 study in Organic Letters reported a novel, high-yield synthetic route using palladium-catalyzed cross-coupling reactions, which significantly improved the scalability and purity of the compound. This methodological advancement is expected to facilitate further pharmacological studies and accelerate the translation of these findings into clinical applications.

Despite these promising developments, challenges remain in the clinical translation of Imidazo[1,2-a]pyridin-7-ol-based therapeutics. Issues such as bioavailability, metabolic stability, and potential off-target effects need to be addressed through comprehensive pharmacokinetic and toxicological studies. However, the growing body of research underscores the potential of this compound as a versatile scaffold for drug discovery, with applications spanning oncology, immunology, and infectious diseases.

In conclusion, the recent studies on Imidazo[1,2-a]pyridin-7-ol (CAS: 896139-85-8) highlight its significant potential in chemical biology and pharmaceutical research. The compound's diverse biological activities, coupled with advancements in synthetic methodologies, position it as a valuable candidate for further investigation. Future research should focus on addressing the remaining challenges and exploring its full therapeutic potential in various disease contexts.

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