Cas no 1446261-31-9 (4-Methyl-1H-indole-2-boronic acid)

4-Methyl-1H-indole-2-boronic acid is a boronic acid derivative of indole, commonly employed as a versatile intermediate in organic synthesis and pharmaceutical research. Its boronic acid functional group enables efficient participation in Suzuki-Miyaura cross-coupling reactions, facilitating the construction of complex heterocyclic frameworks. The methyl substitution at the 4-position enhances stability while maintaining reactivity, making it suitable for selective modifications. This compound is particularly valuable in medicinal chemistry for the development of indole-based bioactive molecules. It exhibits good solubility in common organic solvents, ensuring ease of handling in synthetic applications. Proper storage under inert conditions is recommended to preserve its reactivity.
4-Methyl-1H-indole-2-boronic acid structure
1446261-31-9 structure
Product Name:4-Methyl-1H-indole-2-boronic acid
CAS No:1446261-31-9
MF:C9H10BNO2
MW:174.992202281952
MDL:MFCD11858396
CID:2604557
Update Time:2025-05-26

4-Methyl-1H-indole-2-boronic acid Chemical and Physical Properties

Names and Identifiers

    • 4-Methyl-1H-indole-2-boronic acid
    • (4-methyl-1H-indol-2-yl)boronic acid
    • 2871AJ
    • NE63139
    • Boronic acid, B-(4-methyl-1H-indol-2-yl)-
    • MDL: MFCD11858396
    • Inchi: 1S/C9H10BNO2/c1-6-3-2-4-8-7(6)5-9(11-8)10(12)13/h2-5,11-13H,1H3
    • InChI Key: PCRFOWSRXFBRSB-UHFFFAOYSA-N
    • SMILES: OB(C1=CC2C(C)=CC=CC=2N1)O

Computed Properties

  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 1
  • Complexity: 189
  • Topological Polar Surface Area: 56.2

4-Methyl-1H-indole-2-boronic acid Pricemore >>

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Additional information on 4-Methyl-1H-indole-2-boronic acid

Comprehensive Overview of 4-Methyl-1H-indole-2-boronic acid (CAS No. 1446261-31-9): Properties, Applications, and Research Insights

4-Methyl-1H-indole-2-boronic acid (CAS No. 1446261-31-9) is a specialized boronic acid derivative that has garnered significant attention in pharmaceutical and organic chemistry research. This compound, characterized by its indole core and boronic acid functional group, serves as a versatile building block in Suzuki-Miyaura cross-coupling reactions, a pivotal method for constructing carbon-carbon bonds. Its molecular structure, combining aromaticity and boron-based reactivity, makes it invaluable for synthesizing complex heterocycles and bioactive molecules.

In recent years, the demand for 4-Methyl-1H-indole-2-boronic acid has surged due to its role in developing targeted therapeutics, particularly in oncology and neurology. Researchers are exploring its potential as a precursor for kinase inhibitors and GPCR modulators, aligning with the growing focus on precision medicine. The compound’s boron moiety also enables applications in proteolysis-targeting chimeras (PROTACs), a cutting-edge technology in drug discovery.

From a synthetic perspective, CAS No. 1446261-31-9 exhibits excellent stability under ambient conditions, though it requires storage in anhydrous environments to prevent hydrolysis. Its solubility profile (soluble in polar aprotic solvents like DMSO and THF) facilitates diverse reaction conditions. Analytical techniques such as HPLC and NMR spectroscopy confirm its high purity, critical for reproducible results in catalytic transformations.

The compound’s relevance extends to material science, where its indole scaffold contributes to the design of organic semiconductors and fluorescent probes. Innovations in OLED technology and bioimaging have further driven interest in this derivative. Notably, its low toxicity profile in preliminary studies underscores its suitability for biomedical applications.

Frequently asked questions about 4-Methyl-1H-indole-2-boronic acid include its compatibility with aqueous reaction conditions and optimal catalyst systems for cross-coupling. Recent publications highlight the use of palladium nanoparticles and microwave-assisted synthesis to enhance yields. Environmental considerations, such as green chemistry approaches, are also emerging trends in its utilization.

In summary, 4-Methyl-1H-indole-2-boronic acid (CAS No. 1446261-31-9) represents a cornerstone in modern synthetic chemistry, bridging gaps between drug development, catalysis, and advanced materials. Its multifaceted applications and alignment with industry trends ensure its continued prominence in scientific discourse.

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