Cas no 948593-01-9 ((2-Methyl-1H-indol-6-yl)boronic acid)

(2-Methyl-1H-indol-6-yl)boronic acid is a versatile boronic acid derivative widely used in Suzuki-Miyaura cross-coupling reactions, a key method for constructing carbon-carbon bonds in organic synthesis. The compound features a boronic acid functional group attached to the 6-position of a 2-methylindole scaffold, offering both reactivity and stability under typical coupling conditions. Its indole core provides a privileged heterocyclic structure frequently found in pharmaceuticals and agrochemicals. The methyl substitution at the 2-position enhances steric stability while maintaining reactivity. This reagent is particularly valuable for introducing the 2-methylindole moiety into complex molecules, with applications in medicinal chemistry for drug discovery and material science. It typically exhibits good solubility in common organic solvents like THF and DMSO, facilitating handling in various synthetic protocols. Proper storage under inert atmosphere is recommended to maintain stability.
(2-Methyl-1H-indol-6-yl)boronic acid structure
948593-01-9 structure
Product Name:(2-Methyl-1H-indol-6-yl)boronic acid
CAS No:948593-01-9
MF:C9H10BNO2
MW:174.992202281952
CID:4770717
Update Time:2026-02-26

(2-Methyl-1H-indol-6-yl)boronic acid Chemical and Physical Properties

Names and Identifiers

    • (2-methyl-1H-indol-6-yl)boronic acid
    • Boronic acid, B-(2-methyl-1H-indol-6-yl)-
    • (2-methyl-1H-indol-6-yl)boronicacid
    • SB14921
    • (2-Methyl-1H-indol-6-yl)boronic acid
    • Inchi: 1S/C9H10BNO2/c1-6-4-7-2-3-8(10(12)13)5-9(7)11-6/h2-5,11-13H,1H3
    • InChI Key: MSXJTTAIXHRNOP-UHFFFAOYSA-N
    • SMILES: OB(C1C=CC2C=C(C)NC=2C=1)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

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Additional information on (2-Methyl-1H-indol-6-yl)boronic acid

Comprehensive Overview of (2-Methyl-1H-indol-6-yl)boronic acid (CAS No. 948593-01-9)

(2-Methyl-1H-indol-6-yl)boronic acid (CAS No. 948593-01-9) is a specialized boronic acid derivative widely utilized in organic synthesis, pharmaceutical research, and material science. This compound belongs to the indole boronic acid family, a class of molecules known for their versatility in Suzuki-Miyaura cross-coupling reactions, a cornerstone of modern drug discovery and medicinal chemistry. With the increasing demand for heterocyclic building blocks, this compound has gained significant attention due to its unique structural features and reactivity.

The molecular structure of (2-Methyl-1H-indol-6-yl)boronic acid combines an indole scaffold with a boronic acid functional group, making it a valuable intermediate for constructing complex molecules. Researchers frequently employ it in the synthesis of biologically active compounds, particularly those targeting central nervous system (CNS) disorders and anti-inflammatory agents. Its CAS No. 948593-01-9 is often searched in databases like SciFinder and Reaxys, reflecting its relevance in high-throughput screening and combinatorial chemistry.

In recent years, the compound has been linked to advancements in cancer therapeutics, with studies exploring its role as a precursor for kinase inhibitors and apoptosis inducers. The 2-methylindole moiety enhances metabolic stability, a critical factor in drug design optimization. Additionally, its boronic acid group enables precise C-C bond formation, aligning with the pharmaceutical industry’s push for green chemistry and atom-efficient reactions.

From a commercial perspective, (2-Methyl-1H-indol-6-yl)boronic acid is supplied by leading fine chemical manufacturers under stringent quality control standards. Its applications extend to OLED materials and organic electronics, where indole derivatives contribute to light-emitting efficiency. As the demand for tailor-made intermediates grows, this compound’s synthetic flexibility positions it as a key player in custom synthesis projects.

Environmental and regulatory considerations are also paramount. The compound’s low toxicity profile and compatibility with sustainable solvents (e.g., water or ethanol) make it attractive for eco-friendly synthesis. Laboratories often prioritize it for Pd-catalyzed reactions due to its high purity (>98%) and consistent batch-to-batch reproducibility, addressing the industry’s need for reliable reagents.

Future research directions may explore its potential in proteolysis-targeting chimeras (PROTACs) and bioconjugation techniques, areas trending in biopharmaceutical innovation. With its dual functionality, CAS No. 948593-01-9 remains a focal point for academic-industrial collaborations, bridging gaps between small-molecule development and therapeutic breakthroughs.

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