Cas no 953040-03-4 (5-Bromo-2-chloroquinazolin-8-ol)

5-Bromo-2-chloroquinazolin-8-ol is a halogenated quinazoline derivative with potential applications in pharmaceutical and organic synthesis. Its structure, featuring bromo and chloro substituents along with a hydroxyl group, makes it a versatile intermediate for constructing complex heterocyclic compounds. The bromo and chloro groups enhance reactivity in cross-coupling reactions, while the hydroxyl group allows for further functionalization. This compound is particularly useful in medicinal chemistry for developing kinase inhibitors and other bioactive molecules. Its well-defined molecular framework ensures consistent performance in synthetic pathways, offering researchers a reliable building block for drug discovery and material science applications.
5-Bromo-2-chloroquinazolin-8-ol structure
953040-03-4 structure
Product Name:5-Bromo-2-chloroquinazolin-8-ol
CAS No:953040-03-4
MF:C8H4BrClN2O
MW:259.4872
MDL:MFCD28140217
CID:3032474
Update Time:2025-06-09

5-Bromo-2-chloroquinazolin-8-ol Chemical and Physical Properties

Names and Identifiers

    • 2-氯-5-溴-8-羥基喹唑啉
    • 8-Quinazolinol, 5-bromo-2-chloro-
    • 5-bromo-2-chloro-quinazolin-8-ol
    • 5-BROMO-2-CHLORO-8-QUINAZOLINOL
    • 5-bromo-2-chloroquinazolin-8-ol
    • F15792
    • 5-Bromo-2-chloroquinazolin-8-ol
    • MDL: MFCD28140217
    • Inchi: 1S/C8H4BrClN2O/c9-5-1-2-6(13)7-4(5)3-11-8(10)12-7/h1-3,13H
    • InChI Key: GUUDNCDOVCBQFA-UHFFFAOYSA-N
    • SMILES: BrC1C([H])=C([H])C(=C2C=1C([H])=NC(=N2)Cl)O[H]

Computed Properties

  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 0
  • Complexity: 195
  • XLogP3: 2.8
  • Topological Polar Surface Area: 46

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Additional information on 5-Bromo-2-chloroquinazolin-8-ol

Research Brief on 5-Bromo-2-chloroquinazolin-8-ol (CAS: 953040-03-4): Recent Advances and Applications

5-Bromo-2-chloroquinazolin-8-ol (CAS: 953040-03-4) is a quinazoline derivative that has garnered significant attention in recent years due to its potential applications in medicinal chemistry and drug discovery. Quinazoline derivatives are known for their diverse biological activities, including anticancer, antimicrobial, and anti-inflammatory properties. This research brief synthesizes the latest findings on this compound, focusing on its synthesis, biological activities, and potential therapeutic applications.

Recent studies have highlighted the role of 5-Bromo-2-chloroquinazolin-8-ol as a key intermediate in the synthesis of more complex quinazoline-based compounds. A 2023 study published in the Journal of Medicinal Chemistry demonstrated its utility in the development of kinase inhibitors, particularly targeting EGFR (Epidermal Growth Factor Receptor) and VEGFR (Vascular Endothelial Growth Factor Receptor). These inhibitors are crucial in the treatment of various cancers, including non-small cell lung cancer and colorectal cancer.

In addition to its role in kinase inhibition, 5-Bromo-2-chloroquinazolin-8-ol has shown promise as an antimicrobial agent. A 2022 study in Bioorganic & Medicinal Chemistry Letters reported its efficacy against drug-resistant bacterial strains, such as MRSA (Methicillin-Resistant Staphylococcus aureus). The study attributed this activity to the compound's ability to disrupt bacterial cell wall synthesis, a mechanism distinct from traditional antibiotics.

The synthesis of 5-Bromo-2-chloroquinazolin-8-ol has also seen advancements. A recent patent (US20230183245A1) describes an optimized synthetic route that improves yield and purity while reducing environmental impact. This method employs green chemistry principles, such as solvent-free reactions and catalytic processes, making it more sustainable for large-scale production.

Despite these promising developments, challenges remain. The compound's pharmacokinetic properties, such as bioavailability and metabolic stability, require further optimization. Ongoing research is exploring structural modifications to enhance these properties while retaining its biological activity. For instance, a 2023 preprint on ChemRxiv discusses the introduction of hydrophilic groups to improve solubility without compromising efficacy.

In conclusion, 5-Bromo-2-chloroquinazolin-8-ol (CAS: 953040-03-4) represents a versatile scaffold in drug discovery, with applications ranging from oncology to infectious diseases. Continued research into its mechanisms of action and synthetic optimization will be critical for its translation into clinical applications. This brief underscores the importance of interdisciplinary collaboration in advancing the therapeutic potential of quinazoline derivatives.

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