Cas no 4789-81-5 (Ethyl 2-(quinolin-4-yl)acetate)

Ethyl 2-(quinolin-4-yl)acetate is a versatile organic compound, featuring a quinolin-4-yl group conjugated with an ethyl acetate moiety. This compound exhibits significant advantages in synthetic chemistry, particularly in the synthesis of various quinoline derivatives. Its unique structure allows for effective participation in cross-coupling reactions, providing a valuable tool for organic chemists.
Ethyl 2-(quinolin-4-yl)acetate structure
4789-81-5 structure
Product Name:Ethyl 2-(quinolin-4-yl)acetate
CAS No:4789-81-5
MF:C13H13NO2
MW:215.247823476791
CID:1011653
PubChem ID:3002912
Update Time:2025-07-15

Ethyl 2-(quinolin-4-yl)acetate Chemical and Physical Properties

Names and Identifiers

    • Ethyl 2-(quinolin-4-yl)acetate
    • 4-Quinolineacetic acid ethyl ester
    • ethyl 2-quinolin-4-ylacetate
    • 4789-81-5
    • Quinoline-4-acetic acid ethyl ester
    • DB-070883
    • NAYCHRONYVXKHF-UHFFFAOYSA-N
    • SCHEMBL6174947
    • ETHYL2-(QUINOLIN-4-YL)ACETATE
    • 4-(ethoxycarbonyl methyl)-quinoline
    • DTXSID30388242
    • ethyl 2-(4-quinolyl)acetate
    • SB69877
    • MDL: MFCD03002581
    • Inchi: 1S/C13H13NO2/c1-2-16-13(15)9-10-7-8-14-12-6-4-3-5-11(10)12/h3-8H,2,9H2,1H3
    • InChI Key: NAYCHRONYVXKHF-UHFFFAOYSA-N
    • SMILES: O(CC)C(CC1C=CN=C2C=CC=CC=12)=O

Computed Properties

  • Exact Mass: 215.09469
  • Monoisotopic Mass: 215.094628657g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 4
  • Complexity: 242
  • 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: 2.4
  • Topological Polar Surface Area: 39.2?2

Experimental Properties

  • PSA: 39.19

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Additional information on Ethyl 2-(quinolin-4-yl)acetate

Ethyl 2-(quinolin-4-yl)acetate (CAS No. 4789-81-5): A Comprehensive Overview in Modern Chemical and Pharmaceutical Research

Ethyl 2-(quinolin-4-yl)acetate, chemically identified by the CAS number 4789-81-5, is a compound of significant interest in the realm of chemical and pharmaceutical research. This ester derivative, featuring a quinoline moiety, has garnered attention due to its potential applications in medicinal chemistry and synthetic organic chemistry. The structural uniqueness of Ethyl 2-(quinolin-4-yl)acetate lies in its ability to serve as a versatile intermediate in the synthesis of more complex molecules, particularly those with pharmacological relevance.

The quinoline scaffold, a well-documented heterocyclic system, has been extensively studied for its biological activities. Quinoline derivatives are known for their antimicrobial, antimalarial, and anti-inflammatory properties. The introduction of an acetic ester group at the second position of the quinoline ring in Ethyl 2-(quinolin-4-yl)acetate introduces additional functional handles that can be exploited for further chemical modifications. This makes it a valuable building block for the development of novel therapeutic agents.

In recent years, there has been a surge in research focused on developing new derivatives of quinoline-based compounds due to their demonstrated efficacy in various disease models. The compound Ethyl 2-(quinolin-4-yl)acetate has been explored in several preclinical studies as a precursor for more sophisticated molecules. Its role in the synthesis of kinase inhibitors, particularly those targeting tyrosine kinases, has been highlighted in multiple research publications. These inhibitors are crucial in the treatment of cancers and other chronic diseases where abnormal kinase activity plays a pivotal role.

One of the most compelling aspects of Ethyl 2-(quinolin-4-yl)acetate is its potential as a scaffold for drug discovery. The quinoline ring can be modified in numerous ways to alter its electronic properties and bioavailability. For instance, substituents at different positions on the quinoline ring can influence its binding affinity to biological targets. This flexibility allows researchers to fine-tune the pharmacokinetic and pharmacodynamic properties of derived compounds.

The synthesis of Ethyl 2-(quinolin-4-yl)acetate typically involves the reaction between 4-formylquinoline and ethanol under acidic conditions, leading to the formation of the ester linkage. This reaction is straightforward yet yields a product that is highly reactive and useful in subsequent synthetic steps. The compound's stability under various reaction conditions makes it an ideal candidate for multi-step syntheses without significant degradation.

Recent advancements in computational chemistry have also enhanced the utility of Ethyl 2-(quinolin-4-yl)acetate. Molecular modeling studies have been conducted to predict how modifications to its structure might affect its interactions with biological targets. These studies often involve docking simulations where virtual screening is used to identify potential lead compounds. The insights gained from these simulations have guided experimental efforts, leading to more efficient drug discovery processes.

In addition to its role as a synthetic intermediate, Ethyl 2-(quinolin-4-yl)acetate has been investigated for its potential applications in materials science. Quinoline derivatives are known to exhibit interesting electronic properties, making them suitable candidates for use in organic electronics and photovoltaic devices. While this application is still largely exploratory, it underscores the compound's versatility beyond traditional pharmaceutical uses.

The growing interest in natural product-inspired drug design has also contributed to the study of Ethyl 2-(quinolin-4-yl)acetate. Many natural products contain quinoline-like scaffolds, and synthesizing derivatives of these compounds can provide insights into their biological activities. By studying compounds like Ethyl 2-(quinolin-4-yl)acetate, researchers can uncover new therapeutic strategies that mimic or enhance the effects of these natural products.

Future research directions for Ethyl 2-(quinolin-4-yl)acetate may include exploring its use as a ligand in catalytic systems or as a component in polymer formulations. The compound's ability to participate in various chemical reactions makes it a promising candidate for innovative applications that could bridge gaps between different fields of chemistry and materials science.

In conclusion, Ethyl 2-(quinolin-4-yl)acetate (CAS No. 4789-81-5) is a multifaceted compound with significant potential in both pharmaceutical and materials science research. Its unique structural features make it an invaluable intermediate for synthesizing complex molecules with therapeutic applications. As research continues to evolve, it is likely that new uses and applications for this compound will emerge, further solidifying its importance in modern chemical research.

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