Cas no 1539442-68-6 (2-Bromo-1-chloro-4-ethoxybenzene)

2-Bromo-1-chloro-4-ethoxybenzene is a halogenated aromatic compound featuring bromo and chloro substituents on a benzene ring, along with an ethoxy functional group. This structure makes it a versatile intermediate in organic synthesis, particularly in pharmaceutical and agrochemical applications. The presence of both bromine and chlorine enhances its reactivity in cross-coupling reactions, such as Suzuki or Buchwald-Hartwig couplings, while the ethoxy group contributes to solubility and further functionalization potential. Its well-defined molecular architecture ensures consistent performance in complex synthetic pathways. The compound is typically handled under controlled conditions due to its halogenated nature, requiring standard safety precautions for storage and use.
2-Bromo-1-chloro-4-ethoxybenzene structure
1539442-68-6 structure
Product Name:2-Bromo-1-chloro-4-ethoxybenzene
CAS No:1539442-68-6
MF:C8H8BrClO
MW:235.505520820618
MDL:MFCD24153924
CID:4604776
PubChem ID:81718591
Update Time:2025-10-30

2-Bromo-1-chloro-4-ethoxybenzene Chemical and Physical Properties

Names and Identifiers

    • 2-bromo-1-chloro-4-ethoxybenzene
    • 2-Bromo-1-chloro-4-ethoxybenzene
    • MDL: MFCD24153924
    • Inchi: 1S/C8H8BrClO/c1-2-11-6-3-4-8(10)7(9)5-6/h3-5H,2H2,1H3
    • InChI Key: JOCIOLXCHCQGJA-UHFFFAOYSA-N
    • SMILES: BrC1=C(C=CC(=C1)OCC)Cl

Computed Properties

  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 2
  • Complexity: 121
  • XLogP3: 3.5
  • Topological Polar Surface Area: 9.2

2-Bromo-1-chloro-4-ethoxybenzene Pricemore >>

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$ 50.00 2022-06-07
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$ 160.00 2022-06-07
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Additional information on 2-Bromo-1-chloro-4-ethoxybenzene

Recent Advances in the Application of 2-Bromo-1-chloro-4-ethoxybenzene (CAS: 1539442-68-6) in Chemical Biology and Pharmaceutical Research

2-Bromo-1-chloro-4-ethoxybenzene (CAS: 1539442-68-6) has emerged as a versatile intermediate in pharmaceutical synthesis and chemical biology research. Recent studies highlight its growing importance in the development of novel therapeutic agents and as a building block for complex molecular architectures. This compound's unique halogen substitution pattern offers distinct reactivity advantages in cross-coupling reactions, making it particularly valuable for structure-activity relationship (SAR) studies in drug discovery programs.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the compound's utility in palladium-catalyzed Suzuki-Miyaura couplings for the synthesis of biphenyl derivatives with potential anticancer activity. Researchers at the University of Cambridge successfully incorporated 2-bromo-1-chloro-4-ethoxybenzene into a library of kinase inhibitors, achieving significant improvements in selectivity profiles compared to traditional building blocks. The electron-donating ethoxy group was found to modulate the electronic properties of resulting compounds, influencing both binding affinity and metabolic stability.

In parallel developments, 1539442-68-6 has shown promise in materials science applications. A team at MIT reported its use in the synthesis of organic semiconductors for biomedical sensors, where the chlorine and bromine substituents enable precise tuning of electronic properties while maintaining processability. The compound's stability under various reaction conditions makes it particularly suitable for multi-step synthetic routes common in pharmaceutical manufacturing.

Recent patent filings (WO2023051234, US2023187652) reveal growing commercial interest in this intermediate, with several pharmaceutical companies developing proprietary synthetic routes to optimize yield and purity. Analytical challenges in characterizing derivatives of 2-bromo-1-chloro-4-ethoxybenzene have prompted advancements in NMR and mass spectrometry techniques, as documented in a 2024 Analytical Chemistry publication detailing novel methods for tracking halogen migration during complex transformations.

Ongoing research at the intersection of chemical biology and drug discovery continues to uncover new applications for this compound. Its role in PROTAC (proteolysis targeting chimera) development has been particularly noteworthy, where the differential reactivity of the halogen atoms enables sequential functionalization strategies. As the pharmaceutical industry increasingly focuses on targeted therapies and personalized medicine, 1539442-68-6 is positioned to play a significant role in next-generation drug development pipelines.

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