Cas no 21523-62-6 (Ethyl 2,3-dimethyl-1H-indole-5-carboxylate)

Ethyl 2,3-dimethyl-1H-indole-5-carboxylate is a substituted indole derivative with a carboxylate ester functional group at the 5-position and methyl substituents at the 2- and 3-positions. This compound serves as a versatile intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and functional materials. Its indole core structure is significant in bioactive molecule design, while the ester group enhances reactivity for further derivatization. The dimethyl substitution pattern may influence steric and electronic properties, potentially improving selectivity in synthetic applications. The compound is typically characterized by NMR, MS, and HPLC for purity verification. Proper handling requires standard laboratory precautions due to its organic nature.
Ethyl 2,3-dimethyl-1H-indole-5-carboxylate structure
21523-62-6 structure
Product Name:Ethyl 2,3-dimethyl-1H-indole-5-carboxylate
CAS No:21523-62-6
MF:C13H15NO2
MW:217.263703584671
MDL:MFCD00458330
CID:890397
PubChem ID:612460
Update Time:2025-10-13

Ethyl 2,3-dimethyl-1H-indole-5-carboxylate Chemical and Physical Properties

Names and Identifiers

    • Ethyl 2,3-dimethyl-1H-indole-5-carboxylate
    • 2,3-DIMETHYL-1 H -INDOLE-5-CARBOXYLIC ACID ETHYL ESTER
    • Ethyl 2,3-dimethyl-1{H}-indole-5-carboxylate
    • 2,3-Dimethyl-indol-5-carbonsaeure-aethylester
    • 2,3-Dimethyl-indol-5-carbonsaeure-ethylester
    • 2,3-dimethyl-indole-5-carboxylic acid ethyl ester
    • ethyl 2,3-dimethyl-1H-indol-5-carboxylate
    • Ethyl 2,3-Dimethylindole-5-carboxylate
    • 2,3-Dimethyl-1H-indole-5-carboxylic acid ethyl ester
    • 2,3-dimethyl-1 h-indole-5-carboxylic acid ethyl ester
    • MLS000527700
    • VQDRHZVLRCGSFX-UHFFFAOYSA-N
    • SMR000120274
    • 1H-Indole-5-carboxylic acid, 2,3-dimethyl-, ethyl ester
    • BAS 06489179
    • CBMicro_018317
    • cid_612460
    • BDBM79820
    • HMS1607G13
    • REGID_FOR_
    • MDL: MFCD00458330
    • Inchi: 1S/C13H15NO2/c1-4-16-13(15)10-5-6-12-11(7-10)8(2)9(3)14-12/h5-7,14H,4H2,1-3H3
    • InChI Key: VQDRHZVLRCGSFX-UHFFFAOYSA-N
    • SMILES: O(CC)C(C1C=CC2=C(C=1)C(C)=C(C)N2)=O

Computed Properties

  • Exact Mass: 217.11000
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 3
  • Complexity: 267
  • Topological Polar Surface Area: 42.1

Experimental Properties

  • PSA: 42.09000
  • LogP: 2.96140

Ethyl 2,3-dimethyl-1H-indole-5-carboxylate 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 Ethyl 2,3-dimethyl-1H-indole-5-carboxylate

Ethyl 2,3-dimethyl-1H-indole-5-carboxylate (CAS No. 21523-62-6): A Comprehensive Overview

Ethyl 2,3-dimethyl-1H-indole-5-carboxylate (CAS No. 21523-62-6) is a significant compound in the realm of organic chemistry and pharmaceutical research. This compound, characterized by its unique structural and functional properties, has garnered considerable attention due to its potential applications in drug development and synthetic chemistry. The molecular structure of Ethyl 2,3-dimethyl-1H-indole-5-carboxylate consists of a fused indole ring system with ethyl ester functionality and dimethyl substituents at the 2 and 3 positions. This configuration imparts distinct chemical reactivity and biological activity, making it a valuable intermediate in various synthetic pathways.

The synthesis of Ethyl 2,3-dimethyl-1H-indole-5-carboxylate involves multi-step organic reactions, often starting from readily available precursors such as indole derivatives. The process typically includes alkylation, esterification, and methylation steps to introduce the desired substituents. Advanced synthetic methodologies, including catalytic hydrogenation and palladium-catalyzed cross-coupling reactions, have been employed to enhance yield and purity. These techniques not only improve the efficiency of the synthesis but also minimize unwanted byproducts, ensuring a high-quality final product.

In recent years, Ethyl 2,3-dimethyl-1H-indole-5-carboxylate has been explored for its pharmacological potential. The indole core is a common motif in many bioactive molecules, including pharmaceuticals with antimicrobial, anti-inflammatory, and anticancer properties. The dimethyl substituents at the 2 and 3 positions of the indole ring enhance the compound's solubility and bioavailability, making it more suitable for therapeutic applications. Preliminary studies have indicated that derivatives of this compound exhibit promising activity against certain types of cancer cells by inhibiting key signaling pathways involved in tumor growth.

Moreover, the ester group in Ethyl 2,3-dimethyl-1H-indole-5-carboxylate provides a versatile handle for further functionalization. This allows chemists to modify the compound into more complex structures with tailored biological activities. For instance, hydrolysis of the ester group can yield the corresponding carboxylic acid derivative, which can then be further functionalized through amide bond formation or other chemical transformations. Such modifications are crucial in developing novel drug candidates with enhanced efficacy and reduced side effects.

The pharmaceutical industry has shown interest in exploring new analogs of Ethyl 2,3-dimethyl-1H-indole-5-carboxylate due to its structural features that align well with current drug discovery trends. Computational modeling and high-throughput screening have been utilized to identify potential lead compounds derived from this scaffold. These computational approaches help in predicting the binding affinity of the compound to biological targets, thereby accelerating the drug development process. The integration of machine learning algorithms has further enhanced the precision of these predictions, making virtual screening more efficient.

In addition to its pharmaceutical applications, Ethyl 2,3-dimethyl-1H-indole-5-carboxylate finds utility in materials science and agrochemical research. The unique electronic properties of the indole ring make it a valuable component in organic semiconductors and light-emitting diodes (OLEDs). Researchers have been experimenting with incorporating this compound into polymer matrices to improve charge transport properties in electronic devices. Similarly, in agrochemicals, derivatives of this compound have shown potential as bioactive agents against plant pathogens.

The environmental impact of synthesizing and using Ethyl 2,3-dimethyl-1H-indole-5-carboxylate is also a critical consideration. Efforts are being made to develop greener synthetic routes that minimize waste generation and reduce reliance on hazardous reagents. Biocatalytic methods using enzymes as catalysts have emerged as a promising alternative to traditional chemical synthesis. These methods offer high selectivity and mild reaction conditions, making them environmentally friendly and sustainable.

The future prospects for Ethyl 2,3-dimethyl-1H-indole-5-carboxylate are bright, with ongoing research aimed at uncovering its full potential across various domains. As our understanding of molecular interactions improves through advanced analytical techniques such as nuclear magnetic resonance (NMR) spectroscopy and X-ray crystallography, new insights into its behavior are expected to emerge. Collaborative efforts between academia and industry will be crucial in translating these findings into practical applications.

In conclusion, Ethyl 2,3-dimethyl-1H-indole-5-carboxylate (CAS No. 21523-62-6) is a multifaceted compound with significant implications in pharmaceuticals, materials science, and agrochemicals. Its unique structural features and versatile reactivity make it a valuable building block for developing new drugs and materials. With continued research and innovation, this compound is poised to play an even greater role in addressing global challenges across multiple scientific disciplines.

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