Cas no 143982-39-2 (8-Methylimidazo[1,2-a]pyridine-2-carbaldehyde)

8-Methylimidazo[1,2-a]pyridine-2-carbaldehyde is a heterocyclic aldehyde derivative with a fused imidazo[1,2-a]pyridine core. This compound is of interest in pharmaceutical and organic synthesis due to its versatile reactivity, particularly as a building block for the preparation of more complex heterocyclic systems. The presence of both an aldehyde functional group and a methyl substituent enhances its utility in condensation, nucleophilic addition, and cyclization reactions. Its rigid bicyclic structure contributes to stability while allowing for selective modifications. This makes it valuable in medicinal chemistry for the development of bioactive molecules, including potential therapeutic agents targeting neurological and inflammatory pathways. High purity and consistent quality are critical for reproducible results in research applications.
8-Methylimidazo[1,2-a]pyridine-2-carbaldehyde structure
143982-39-2 structure
Product Name:8-Methylimidazo[1,2-a]pyridine-2-carbaldehyde
CAS No:143982-39-2
MF:C9H8N2O
MW:160.17262172699
MDL:MFCD06739274
CID:108559
PubChem ID:11094924
Update Time:2025-06-08

8-Methylimidazo[1,2-a]pyridine-2-carbaldehyde Chemical and Physical Properties

Names and Identifiers

    • 8-Methylimidazo[1,2-a]pyridine-2-carbaldehyde
    • 8-METHYL-IMIDAZO[1,2-A]PYRIDINE-2-CARBALDEHYDE
    • Imidazo[1,2-a]pyridine-2-carboxaldehyde,8-methyl-
    • imidazo<1,2-a>azinecarbaldehyde
    • A23530
    • SY322804
    • AM803214
    • AB29016
    • 8-METHYLIMIDAZO[1,2-A]PYRIDINE-2-CARBOXALDEHYDE
    • CS-0084907
    • FT-0742273
    • Imidazo[1,2-a]pyridine-2-carboxaldehyde, 8-methyl- (9CI)
    • SCHEMBL4891529
    • AS-82562
    • MFCD06739274
    • 8-Methyl-imidazo[1,2-a]pyridine-2-carbaldehyde, AldrichCPR
    • AKOS006292885
    • J-501389
    • DTXSID50454938
    • 143982-39-2
    • ZUQFHQQPWQVWSO-UHFFFAOYSA-N
    • BCP26318
    • DB-063509
    • MDL: MFCD06739274
    • Inchi: 1S/C9H8N2O/c1-7-3-2-4-11-5-8(6-12)10-9(7)11/h2-6H,1H3
    • InChI Key: ZUQFHQQPWQVWSO-UHFFFAOYSA-N
    • SMILES: O=CC1=CN2C=CC=C(C)C2=N1

Computed Properties

  • Exact Mass: 160.06400
  • Monoisotopic Mass: 160.063662883g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 1
  • Complexity: 183
  • 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: 1.9
  • Topological Polar Surface Area: 34.4?2

Experimental Properties

  • Density: 1.21
  • PSA: 34.37000
  • LogP: 1.45520

8-Methylimidazo[1,2-a]pyridine-2-carbaldehyde 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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8-Methylimidazo[1,2-a]pyridine-2-carbaldehyde Production Method

Additional information on 8-Methylimidazo[1,2-a]pyridine-2-carbaldehyde

Introduction to 8-Methylimidazo[1,2-a]pyridine-2-carbaldehyde (CAS No. 143982-39-2) and Its Emerging Applications in Chemical Biology and Medicinal Chemistry

8-Methylimidazo[1,2-a]pyridine-2-carbaldehyde, identified by the chemical identifier CAS No. 143982-39-2, is a heterocyclic compound that has garnered significant attention in the fields of chemical biology and medicinal chemistry due to its unique structural properties and versatile reactivity. This compound belongs to the imidazopyridine class, a scaffold that has been extensively explored for its potential in drug discovery and development. The presence of a carbaldhyde functional group at the 2-position of the imidazopyridine core enhances its utility as a key intermediate in synthetic chemistry, enabling the construction of more complex molecules with therapeutic relevance.

The imidazopyridine core is a privileged structure in medicinal chemistry, known for its ability to interact with biological targets such as enzymes and receptors. The 8-Methylimidazo[1,2-a]pyridine-2-carbaldehyde derivative has been studied for its pharmacological properties, particularly in the context of anticancer and anti-inflammatory applications. Recent research has highlighted its role as a precursor in the synthesis of small-molecule inhibitors that modulate critical biological pathways. The aldehyde group at the 2-position provides a reactive handle for further functionalization, allowing chemists to design molecules with tailored biological activities.

One of the most compelling aspects of 8-Methylimidazo[1,2-a]pyridine-2-carbaldehyde is its potential as a building block for drug candidates. The imidazopyridine scaffold is found in several approved drugs, demonstrating its feasibility as a pharmacophore. Studies have demonstrated that derivatives of this compound can exhibit inhibitory effects on kinases and other enzymes involved in cancer progression. The CAS No. 143982-39-2 identifier ensures unambiguous identification, which is crucial for reproducibility in scientific research and industrial applications.

In recent years, there has been growing interest in developing novel therapeutic agents based on heterocyclic compounds. 8-Methylimidazo[1,2-a]pyridine-2-carbaldehyde has been employed in the synthesis of molecules that target specific disease pathways. For instance, researchers have explored its utility in creating inhibitors of Janus kinases (JAKs), which play a pivotal role in inflammatory responses. The ability to modify the imidazopyridine core allows for fine-tuning of binding interactions with biological targets, making it an attractive scaffold for structure-activity relationship (SAR) studies.

The reactivity of the carbaldhyde group in 8-Methylimidazo[1,2-a]pyridine-2-carbaldehyde enables diverse chemical transformations, including condensation reactions with amines to form Schiff bases and other nitrogen-containing heterocycles. These derivatives have been investigated for their antimicrobial and anti-inflammatory properties. Additionally, the compound has been used in cross-coupling reactions such as Suzuki-Miyaura and Buchwald-Hartwig couplings, which are fundamental techniques in modern organic synthesis. These reactions facilitate the introduction of aryl or amino groups at various positions of the imidazopyridine ring, expanding the chemical space available for drug discovery.

Advances in computational chemistry have further enhanced the utility of 8-Methylimidazo[1,2-a]pyridine-2-carbaldehyde as a drug-like scaffold. Molecular modeling studies have predicted favorable binding modes of this compound with biological targets, guiding rational design strategies. Virtual screening campaigns have identified novel derivatives with enhanced potency and selectivity. These computational approaches complement experimental efforts by providing insights into ligand-receptor interactions at an atomic level.

The pharmaceutical industry has recognized the potential of imidazopyridine derivatives like 8-Methylimidazo[1,2-a]pyridine-2-carbaldehyde as lead compounds for new therapies. Several companies are actively engaged in developing small-molecule inhibitors based on this scaffold for treating conditions such as cancer and autoimmune diseases. The versatility of this compound lies in its ability to be modified at multiple positions while retaining core pharmacological activity. This flexibility allows medicinal chemists to optimize properties such as solubility, bioavailability, and metabolic stability.

In conclusion,8-Methylimidazo[1,2-a]pyridine-2-carbaldehyde (CAS No. 143982-39-2) represents a promising candidate for further exploration in chemical biology and medicinal chemistry. Its unique structural features and reactivity make it an invaluable tool for synthesizing novel drug candidates targeting various diseases. As research continues to uncover new applications for this compound,imidazopyridine derivatives are likely to play an increasingly significant role in future therapeutics.

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