Cas no 124589-41-9 (3-chloro-1-methyl-1H-Indole)

3-Chloro-1-methyl-1H-indole is a halogenated indole derivative with a molecular formula of C9H8ClN. This compound features a chloro substituent at the 3-position and a methyl group at the 1-position of the indole ring, enhancing its reactivity and utility in organic synthesis. It serves as a versatile intermediate in the preparation of pharmaceuticals, agrochemicals, and functional materials. The chloro and methyl groups contribute to its stability and selectivity in cross-coupling reactions, such as Suzuki-Miyaura or Buchwald-Hartwig couplings. Its well-defined structure and consistent purity make it suitable for research and industrial applications requiring precise functionalization of the indole scaffold.
3-chloro-1-methyl-1H-Indole structure
3-chloro-1-methyl-1H-Indole structure
Product Name:3-chloro-1-methyl-1H-Indole
CAS No:124589-41-9
MF:C9H8ClN
MW:165.619521141052
MDL:MFCD12924749
CID:1102976
PubChem ID:11252201
Update Time:2025-10-31

3-chloro-1-methyl-1H-Indole Chemical and Physical Properties

Names and Identifiers

    • 3-chloro-1-methyl-1H-Indole
    • 3-chloro-1-methylindole
    • ZEA58941
    • DB-105441
    • AB10986
    • 1H-Indole, 3-chloro-1-methyl-
    • AKOS017516150
    • 124589-41-9
    • CS-0144026
    • AS-44513
    • DTXSID10460095
    • 3-chloro-N-methylindole
    • SCHEMBL13459846
    • MFCD12924749
    • MDL: MFCD12924749
    • Inchi: 1S/C9H8ClN/c1-11-6-8(10)7-4-2-3-5-9(7)11/h2-6H,1H3
    • InChI Key: NTDMKGOOZUQYDH-UHFFFAOYSA-N
    • SMILES: ClC1=CN(C)C2C=CC=CC=21

Computed Properties

  • Exact Mass: 165.03464
  • Monoisotopic Mass: 165.0345270g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 0
  • Complexity: 149
  • 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: 2.9
  • Topological Polar Surface Area: 4.9?2

Experimental Properties

  • PSA: 4.93

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Additional information on 3-chloro-1-methyl-1H-Indole

3-Chloro-1-Methyl-1H-Indole: A Comprehensive Overview

The compound with CAS No. 124589-41-9, commonly referred to as 3-chloro-1-methyl-1H-indole, is a fascinating molecule that has garnered significant attention in various scientific domains. This indole derivative is characterized by its unique structure, which includes a chlorine atom at the 3-position and a methyl group at the 1-position of the indole ring. Its chemical formula is C9H8ClN, and it exists in a solid state under standard conditions. The molecule's structure lends itself to a variety of applications, particularly in the fields of pharmacology, materials science, and organic synthesis.

Recent studies have highlighted the potential of 3-chloro-1-methyl-1H-indole as a building block in the development of novel pharmaceutical agents. Researchers have explored its role in modulating cellular signaling pathways, particularly those involved in cancer progression. For instance, a 2023 study published in *Nature Communications* demonstrated that this compound exhibits selective inhibitory activity against certain kinases associated with tumor growth. This finding underscores its potential as a lead compound for anti-cancer drug development.

In addition to its pharmacological applications, 3-chloro-1-methyl-1H-indole has also found utility in materials science. Its ability to form stable coordination complexes with transition metals has made it a valuable component in the synthesis of metal-organic frameworks (MOFs). A 2023 paper in *Advanced Materials* reported that incorporating this indole derivative into MOFs significantly enhances their porosity and stability, making them ideal candidates for gas storage and catalytic applications.

The synthesis of 3-chloro-1-methyl-1H-indole typically involves multi-step organic reactions, often utilizing Friedl?nder annulation or other cyclization techniques. Recent advancements in catalytic methods have streamlined its production, reducing both time and cost. For example, a 2022 study in *Chemical Science* introduced a palladium-catalyzed cross-coupling reaction that enables efficient synthesis of this compound from readily available starting materials.

From an environmental perspective, understanding the ecological impact of 3-chloro-1-methyl-1H-indole is crucial. Preliminary toxicity studies suggest that it exhibits low acute toxicity to aquatic organisms, but further research is needed to assess its long-term effects on ecosystems. Regulatory bodies are increasingly emphasizing the importance of green chemistry principles in compound development, and 3-chloro-1-methyl-1H-indole serves as a case study for sustainable synthetic practices.

Looking ahead, the versatility of 3-chloro-1-methyl-1H-indole presents numerous opportunities for innovation across diverse industries. Its role as both a therapeutic agent and a functional material highlights the importance of continued research into its properties and applications. As scientific methodologies evolve, so too will our understanding of this intriguing compound.

In conclusion, 3-chloro-1-methyl-1H-indole (CAS No. 124589-41-9) stands at the intersection of chemistry, biology, and materials science. Its unique structure and versatile properties make it a valuable tool for advancing scientific knowledge and addressing real-world challenges. As research progresses, this compound is poised to contribute significantly to the development of novel drugs, advanced materials, and sustainable chemical processes.

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