Cas no 80906-24-7 (3-Bromo-1,2-dimethyl-1H-indole)

3-Bromo-1,2-dimethyl-1H-indole structure
80906-24-7 structure
Product Name:3-Bromo-1,2-dimethyl-1H-indole
CAS No:80906-24-7
MF:C10H10BrN
MW:224.097101688385
MDL:MFCD11893509
CID:704838
PubChem ID:11299039
Update Time:2025-04-23

3-Bromo-1,2-dimethyl-1H-indole Chemical and Physical Properties

Names and Identifiers

    • 1H-Indole, 3-bromo-1,2-dimethyl-
    • 3-bromo-1,2-dimethylindole
    • 3-Bromo-1,2-dimethyl-1H-indole
    • MFCD11893509
    • EN300-1912358
    • AKOS016389993
    • DTXSID70461629
    • NS-02763
    • 80906-24-7
    • MDL: MFCD11893509
    • Inchi: 1S/C10H10BrN/c1-7-10(11)8-5-3-4-6-9(8)12(7)2/h3-6H,1-2H3
    • InChI Key: IWOBAONZGDLVQJ-UHFFFAOYSA-N
    • SMILES: BrC1=C(C)N(C)C2C=CC=CC=21

Computed Properties

  • Exact Mass: 222.99966g/mol
  • Monoisotopic Mass: 222.99966g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 0
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 0
  • Complexity: 171
  • 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: 3
  • Topological Polar Surface Area: 4.9?2

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Additional information on 3-Bromo-1,2-dimethyl-1H-indole

1H-Indole, 3-bromo-1,2-dimethyl- (CAS No. 80906-24-7): A Key Intermediate in Modern Pharmaceutical Synthesis

The compound 1H-Indole, 3-bromo-1,2-dimethyl, identified by its CAS number 80906-24-7, represents a significant intermediate in the realm of pharmaceutical chemistry. This heterocyclic aromatic molecule, characterized by a brominated indole core with dimethyl substitutions at the 1 and 2 positions, has garnered considerable attention due to its versatile reactivity and utility in synthesizing biologically active molecules. The structural features of this compound make it a valuable building block for the development of novel therapeutic agents, particularly in the areas of oncology and infectious diseases.

In recent years, the pharmaceutical industry has witnessed a surge in the exploration of indole derivatives as potential drug candidates. The indole scaffold, known for its presence in numerous pharmacologically active compounds, offers a rich platform for structural modifications. Among these modifications, the introduction of bromine at the 3-position and methyl groups at the 1 and 2 positions enhances the electrophilicity of the molecule, facilitating further functionalization through cross-coupling reactions such as Suzuki-Miyaura and Buchwald-Hartwig couplings. These reactions are pivotal in constructing complex molecular architectures essential for drug design.

One of the most compelling applications of 1H-Indole, 3-bromo-1,2-dimethyl is in the synthesis of small-molecule inhibitors targeting protein-protein interactions. Protein-protein interactions play a crucial role in various cellular processes, and modulating these interactions has emerged as a promising strategy for therapeutic intervention. For instance, indole derivatives have been investigated for their potential to disrupt oncogenic signaling pathways by inhibiting key transcription factors and kinases. The brominated indole derivative serves as an excellent precursor for generating libraries of compounds that can be screened for their ability to modulate these interactions.

Moreover, the compound has shown promise in the development of antiviral agents. The bromine atom at the 3-position provides a handle for further derivatization, allowing chemists to introduce groups that can interact with viral enzymes or receptors. Recent studies have highlighted the use of indole-based molecules in combating viral infections by inhibiting replication or entry into host cells. The dimethyl substitution at the 1 and 2 positions enhances metabolic stability while maintaining bioactivity, making this derivative an attractive candidate for further development.

The synthesis of 1H-Indole, 3-bromo-1,2-dimethyl typically involves multi-step organic transformations starting from commercially available precursors such as tryptophan or tryptamine derivatives. The bromination step is often performed using brominating agents like N-bromosuccinimide (NBS) under controlled conditions to ensure regioselectivity. Subsequent alkylation with methylating agents such as iodomethane or dimethyl sulfate completes the formation of the desired dimethylated indole structure. These synthetic routes highlight the compound's accessibility and scalability, which are critical factors in pharmaceutical development.

Advances in computational chemistry have further enhanced the utility of 1H-Indole, 3-bromo-1,2-dimethyl by enabling rapid virtual screening and molecular docking studies. These computational methods allow researchers to predict binding affinities and optimize lead structures before proceeding to costly experimental synthesis. By leveraging machine learning algorithms trained on large datasets of known drug candidates, scientists can identify novel analogs of this compound with improved pharmacokinetic properties and reduced toxicity.

The role of 1H-Indole, 3-bromo-1,2-dimethyl extends beyond its direct use as a drug intermediate; it also serves as a valuable tool in medicinal chemistry research. Its unique structural features allow chemists to explore diverse chemical space by introducing various functional groups through palladium-catalyzed cross-coupling reactions. This flexibility has led to the discovery of several potent inhibitors with therapeutic potential against a range of diseases.

In conclusion,1H-Indole, 3-bromo-1,2-dimethyl (CAS No. 80906-24-7) is a multifaceted compound with significant applications in pharmaceutical synthesis. Its ability to undergo selective functionalization makes it an indispensable intermediate for developing novel therapeutic agents targeting various diseases. As research continues to uncover new biological targets and synthetic methodologies,1H-Indole, 3-bromo-1,2-dimethyl will undoubtedly remain at the forefront of medicinal chemistry innovation.

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