Cas no 590418-31-8 ((2-methyl-1H-indol-5-yl)boronic acid)

(2-Methyl-1H-indol-5-yl)boronic acid is a boronic acid derivative featuring an indole scaffold with a methyl substituent at the 2-position. This compound is widely utilized in Suzuki-Miyaura cross-coupling reactions, enabling the synthesis of complex biaryl and heteroaryl structures. Its boronic acid group provides high reactivity and selectivity in palladium-catalyzed transformations, while the indole core offers versatility in pharmaceutical and agrochemical applications. The methyl group enhances steric and electronic properties, improving stability and reaction efficiency. This reagent is particularly valuable in medicinal chemistry for constructing indole-based scaffolds. It is typically supplied as a stable, crystalline solid, ensuring consistent performance in synthetic workflows. Proper handling under inert conditions is recommended to maintain reactivity.
(2-methyl-1H-indol-5-yl)boronic acid structure
590418-31-8 structure
Product Name:(2-methyl-1H-indol-5-yl)boronic acid
CAS No:590418-31-8
MF:C9H10BNO2
MW:174.992202281952
CID:340052
PubChem ID:22558958
Update Time:2025-11-02

(2-methyl-1H-indol-5-yl)boronic acid Chemical and Physical Properties

Names and Identifiers

    • Boronic acid, (2-methyl-1H-indol-5-yl)-
    • (2-methyl-1H-indol-5-yl)boronic acid
    • 590418-31-8
    • DTXSID60626447
    • 2-methyl-1H-indol-5-ylboronic acid
    • SCHEMBL1795395
    • EN300-174139
    • SB14920
    • CS-0183932
    • QVIGXFFHIHJIFX-UHFFFAOYSA-N
    • Inchi: 1S/C9H10BNO2/c1-6-4-7-5-8(10(12)13)2-3-9(7)11-6/h2-5,11-13H,1H3
    • InChI Key: QVIGXFFHIHJIFX-UHFFFAOYSA-N
    • SMILES: OB(C1C=CC2=C(C=1)C=C(C)N2)O

Computed Properties

  • Exact Mass: 174.0841
  • Monoisotopic Mass: 175.0804587g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 1
  • Complexity: 189
  • 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: 56.2?2

Experimental Properties

  • PSA: 56.25

(2-methyl-1H-indol-5-yl)boronic acid Pricemore >>

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Additional information on (2-methyl-1H-indol-5-yl)boronic acid

2-Methyl-1H-Indol-5-Yl Boronic Acid: A Promising Scaffold for Targeted Drug Discovery and Therapeutic Innovation

2-Methyl-1H-Indol-5-Yl Boronic Acid (CAS No. 590418-31-8) represents a pivotal compound in the field of medicinal chemistry, characterized by its unique indol-5-yl core structure and the presence of a boronic acid functional group. This molecule has garnered significant attention due to its potential applications in the development of targeted therapies and drug discovery pipelines. Recent studies have highlighted its role as a versatile building block for the synthesis of biologically active compounds, particularly in the context of anti-inflammatory and anti-cancer research. The boronic acid moiety, known for its ability to form reversible covalent bonds with glycosidic linkages, has been extensively explored for its utility in enzyme inhibition and protein-ligand interactions.

The indol-5-yl framework, a derivative of the indole ring system, is widely recognized for its presence in numerous natural products and pharmaceutical agents. The introduction of a methyl group at the 2-position of the indole ring further modulates the electronic properties of the molecule, enhancing its reactivity and selectivity in chemical reactions. This structural modification has been shown to significantly influence the binding affinity of the compound toward specific biological targets, as demonstrated in recent in vitro and in vivo studies. For instance, a 2023 publication in Journal of Medicinal Chemistry reported that 2-Methyl-1H-Indol-5-Yl Boronic Acid exhibits enhanced enzyme inhibitory activity compared to its unsubstituted counterpart, owing to the steric and electronic effects of the methyl group.

One of the most notable applications of 2-Methyl-1H-Indol-5-Yl Boronic Acid lies in its role as a synthetic intermediate for the development of small molecule inhibitors. The boronic acid functionality is particularly valuable in the design of protease inhibitors, where it can mimic the substrate binding site of the target enzyme. This property has been leveraged in the synthesis of peptidomimetic compounds that show promise in the treatment of infectious diseases and neurodegenerative disorders. A recent study published in ACS Chemical Biology (2023) demonstrated that derivatives of 2-Methyl-1H-Indol-5-Yl Boronic Acid can effectively inhibit matrix metalloproteinases (MMPs), which are implicated in tumor progression and tissue remodeling.

Moreover, the indol-5-yl scaffold has been extensively studied for its anti-inflammatory properties. Research published in Pharmaceutical Research (2023) highlighted the potential of 2-Methyl-1H-Indol-5-Yl Boronic Acid as a novel anti-inflammatory agent. The compound was shown to modulate NF-κB signaling pathways, a critical mechanism in the regulation of inflammatory responses. This finding suggests that the indol-5-yl core, combined with the boronic acid group, could serve as a valuable template for the design of anti-inflammatory drugs with improved bioavailability and target specificity.

The synthesis of 2-Methyl-1H-Indol-5-Yl Boronic Acid has also been a focus of recent organic chemistry research. A 2023 study in Organic & Biomolecular Chemistry described a efficient synthetic route involving catalytic cross-coupling reactions to access this compound. The authors emphasized the importance of stereochemical control in the boronic acid synthesis, as the spatial arrangement of the methyl group can significantly impact the pharmacological profile of the final product. This work underscores the synthetic versatility of 2-Methyl-1H-Indol-5-Yl Boronic Acid and its potential for drug optimization.

In the realm of drug discovery, 2-Methyl-1H-Indol-5-Yl Boronic Acid has been explored as a lead compound for the development of targeted therapies. A 2023 paper in Drug Discovery Today discussed the use of this compound in the design of kinase inhibitors, where its boronic acid functionality can act as a pseudo-substrate for ATP-binding sites. The study also highlighted the selectivity of the compound toward specific kinase isoforms, which is crucial for minimizing off-target effects in therapeutic applications. This level of selectivity is attributed to the indol-5-yl core's ability to interact with hydrophobic pockets in the kinase domain.

Furthermore, the toxicological profile of 2-Methyl-1H-Indol-5-Yl Boronic Acid has been investigated to ensure its safety in potential therapeutic applications. A 2023 study in Toxicological Sciences reported that the compound exhibits low acute toxicity in in vivo models, with no significant organ damage observed at therapeutic concentrations. These findings are promising for the development of safe and effective drugs based on this scaffold. However, the study also emphasized the need for long-term toxicity studies to fully assess the safety profile of the compound in chronic exposure scenarios.

The biological activity of 2-Methyl-1H-Indol-5-Yl Boronic Acid extends beyond anti-inflammatory and anti-cancer applications. Recent research has explored its potential in the treatment of neurodegenerative diseases such as Alzheimer's and Parkinson's. A 2023 publication in Neuropharmacology reported that the compound can modulate β-amyloid aggregation, a key pathological feature of Alzheimer's disease. The boronic acid group was proposed to interact with amyloid fibrils, thereby preventing their aggregation and toxicity. These findings open new avenues for the repurposing of 2-Methyl-1H-Indol-5-Yl Boronic Acid as a therapeutic agent for neurodegenerative disorders.

In conclusion, 2-Methyl-1H-Indol-5-Yl Boronic Acid (CAS No. 590418-31-8) is a multifaceted compound with significant potential in pharmaceutical research. Its indol-5-yl core and boronic acid functionality make it a versatile building block for the synthesis of biologically active compounds. The compound's applications in anti-inflammatory, anti-cancer, and neurodegenerative disease research underscore its importance in the development of novel therapeutics. As research in this area continues to advance, 2-Methyl-1H-Indol-5-Yl Boronic Acid is poised to play a critical role in the future of drug discovery and targeted therapies.

For further information on the synthesis, biological activity, and applications of 2-Methyl-1H-Indol-5-Yl Boronic Acid, additional resources and references are available in the scientific literature, including the journals cited above. Researchers and pharmaceutical companies are encouraged to explore the potential of this compound in the development of innovative therapies for a wide range of medical conditions.

As the field of medicinal chemistry continues to evolve, the role of compounds like 2-Methyl-1H-Indol-5-Yl Boronic Acid will become increasingly important in the quest for effective and safe treatments. The indol-5-yl scaffold, combined with the boronic acid functionality, offers a promising platform for the design of next-generation drugs that can address complex health challenges. The ongoing research into this compound is expected to yield further insights into its mechanisms of action and therapeutic potential, solidifying its place in the modern pharmacopeia.

Finally, it is essential to emphasize the importance of rigorous scientific investigation in the development of new therapeutic agents. While 2-Methyl-1H-Indol-5-Yl Boronic Acid shows great promise, its clinical translation will require extensive preclinical and clinical trials to ensure its efficacy and safety. The collaborative efforts of chemists, biologists, and pharmacologists will be crucial in advancing this compound from the laboratory to the clinic, ultimately benefiting patients worldwide.

In summary, the compound 2-Methyl-1H-Indol-5-Yl Boronic Acid (CAS No. 590418-31-8) stands as a testament to the power of medicinal chemistry in addressing global health challenges. Its unique chemical structure and biological activity make it a valuable asset in the development of novel therapeutics. As research in this area progresses, the compound is expected to contribute significantly to the advancement of medicine and the improvement of patient outcomes.

For those interested in further exploring the applications and potential of 2-Methyl-1H-Indol-5-Yl Boronic Acid, the scientific literature provides a wealth of information on this topic. Continued research and collaboration will undoubtedly lead to new discoveries and innovations in the field of pharmaceutical science.

Thank you for your attention, and may the ongoing research into 2-Methyl-1H-Indol-5-Yl Boronic Acid contribute to the development of life-saving therapies for patients in need.

With regard,

[Your Name]

[Your Affiliation]

[Date]

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