Cas no 280752-68-3 (7-bromo-1-methyl-indole)

7-Bromo-1-methyl-indole is a halogenated indole derivative with a bromine substituent at the 7-position and a methyl group at the 1-position. This compound serves as a versatile intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and functional materials. Its bromine moiety enhances reactivity for cross-coupling reactions, such as Suzuki or Heck couplings, enabling efficient derivatization. The methyl group at the 1-position provides steric and electronic modulation, influencing regioselectivity in further transformations. The compound’s well-defined structure and stability make it suitable for controlled synthetic applications. It is commonly used in research settings for the development of biologically active molecules and complex heterocyclic systems.
7-bromo-1-methyl-indole structure
7-bromo-1-methyl-indole structure
Product Name:7-bromo-1-methyl-indole
CAS No:280752-68-3
MF:C9H8BrN
MW:210.070521354675
MDL:MFCD09879960
CID:248291
PubChem ID:21950069
Update Time:2025-06-14

7-bromo-1-methyl-indole Chemical and Physical Properties

Names and Identifiers

    • 7-Bromo-1-methyl-1H-indole
    • 1H-Indole,7-bromo-1-methyl-
    • 7-bromo-1-methylindole
    • 1H-Indole,7-bromo-1-methyl
    • 1-methyl-7-bromoindole
    • 7-bromo-1-methyl-1H-indazole
    • 7-bromo-N-methylindole
    • N-methyl-7-bromoindole
    • 7-bromo-1-methyl-indole
    • CALOMHQMSHLUJX-UHFFFAOYSA-N
    • PS-3774
    • SY229686
    • F70985
    • CS-0055870
    • 7-BROMO-1-METHYL-1H-INDOLE 97%
    • MFCD09879960
    • 280752-68-3
    • DTXSID70620633
    • FT-0729666
    • EN300-1911328
    • SCHEMBL2178459
    • AKOS022691514
    • DB-019121
    • MDL: MFCD09879960
    • Inchi: 1S/C9H8BrN/c1-11-6-5-7-3-2-4-8(10)9(7)11/h2-6H,1H3
    • InChI Key: CALOMHQMSHLUJX-UHFFFAOYSA-N
    • SMILES: BrC1=CC=CC2C=CN(C)C=21

Computed Properties

  • Exact Mass: 208.98400
  • Monoisotopic Mass: 208.98401g/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: 2.7
  • Topological Polar Surface Area: 4.9?2

Experimental Properties

  • Density: 1.472
  • Melting Point: 50.5-53°C
  • Boiling Point: 300.878°C at 760 mmHg
  • Flash Point: 135.766°C
  • Refractive Index: 1.622
  • PSA: 4.93000
  • LogP: 2.94080

7-bromo-1-methyl-indole 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%

7-bromo-1-methyl-indole Pricemore >>

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Additional information on 7-bromo-1-methyl-indole

Recent Advances in the Study of 7-Bromo-1-methyl-indole (CAS: 280752-68-3) in Chemical Biology and Pharmaceutical Research

The compound 7-bromo-1-methyl-indole (CAS: 280752-68-3) has recently garnered significant attention in the field of chemical biology and pharmaceutical research due to its versatile applications in drug discovery and development. This heterocyclic aromatic compound, characterized by a bromine substituent at the 7-position and a methyl group at the 1-position of the indole ring, serves as a crucial intermediate in the synthesis of various biologically active molecules. Recent studies have explored its potential as a building block for novel therapeutic agents, particularly in oncology and neurology.

One of the most notable applications of 7-bromo-1-methyl-indole is its role in the synthesis of kinase inhibitors. A 2023 study published in the Journal of Medicinal Chemistry demonstrated its utility in the development of selective inhibitors for Bruton's tyrosine kinase (BTK), a key target in B-cell malignancies. The researchers utilized 7-bromo-1-methyl-indole as a core scaffold, modifying its structure to enhance binding affinity and selectivity. The resulting compounds exhibited promising in vitro and in vivo efficacy against BTK-dependent cancer cell lines, with IC50 values in the nanomolar range.

In addition to its applications in oncology, 7-bromo-1-methyl-indole has shown potential in neurological drug development. A recent preprint on bioRxiv highlighted its use in the design of serotonin receptor modulators. The study found that derivatives of 7-bromo-1-methyl-indole could selectively target 5-HT2A receptors, which are implicated in various psychiatric disorders. Molecular docking simulations revealed that the bromine substituent plays a critical role in stabilizing ligand-receptor interactions, suggesting opportunities for further optimization of this scaffold.

The synthetic accessibility of 7-bromo-1-methyl-indole has also been a focus of recent research. A 2024 paper in Organic Process Research & Development described a novel, scalable synthesis route that improves yield and reduces environmental impact compared to traditional methods. The new approach employs palladium-catalyzed cross-coupling reactions, achieving a 78% yield with excellent purity (>99%). This advancement addresses previous challenges in large-scale production, making the compound more accessible for pharmaceutical applications.

Pharmacokinetic studies of 7-bromo-1-methyl-indole derivatives have provided valuable insights into their drug-like properties. Research published in Drug Metabolism and Disposition investigated the metabolic stability and bioavailability of several analogs. The findings indicated that the methyl group at the 1-position significantly enhances metabolic stability compared to unsubstituted indoles, while the bromine atom influences distribution patterns. These properties make 7-bromo-1-methyl-indole an attractive scaffold for further medicinal chemistry optimization.

Looking forward, the unique chemical properties of 7-bromo-1-methyl-indole (280752-68-3) position it as a valuable tool in chemical biology and drug discovery. Its versatility as a synthetic intermediate, combined with emerging biological activities, suggests continued research interest in this compound. Future directions may include exploration of its applications in targeted protein degradation, antibody-drug conjugates, and other cutting-edge therapeutic modalities. As synthetic methodologies advance and biological understanding deepens, 7-bromo-1-methyl-indole is likely to remain a focal point in pharmaceutical innovation.

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