Cas no 1644663-98-8 (6-Bromo-2,5-dichloroquinazoline)

6-Bromo-2,5-dichloroquinazoline is a halogenated quinazoline derivative widely utilized as a versatile intermediate in organic synthesis and pharmaceutical research. Its distinct bromo- and dichloro-substitutions enhance reactivity, facilitating selective functionalization in cross-coupling reactions and nucleophilic substitutions. The compound’s rigid quinazoline core contributes to its stability, making it suitable for constructing complex heterocyclic frameworks. It is particularly valuable in medicinal chemistry for developing kinase inhibitors and other biologically active molecules. High purity grades ensure consistent performance in research and industrial applications. Proper handling under controlled conditions is recommended due to its halogenated nature.
6-Bromo-2,5-dichloroquinazoline structure
1644663-98-8 structure
Product Name:6-Bromo-2,5-dichloroquinazoline
CAS No:1644663-98-8
MF:C8H3BrCl2N2
MW:277.932818651199
MDL:MFCD28405535
CID:4821651
Update Time:2026-02-27

6-Bromo-2,5-dichloroquinazoline Chemical and Physical Properties

Names and Identifiers

    • 6-Bromo-2,5-dichloroquinazoline
    • MDL: MFCD28405535
    • Inchi: 1S/C8H3BrCl2N2/c9-5-1-2-6-4(7(5)10)3-12-8(11)13-6/h1-3H
    • InChI Key: WPKJKJUGPOBQMU-UHFFFAOYSA-N
    • SMILES: BrC1C=CC2C(=CN=C(N=2)Cl)C=1Cl

Computed Properties

  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 0
  • Complexity: 193
  • XLogP3: 3.8
  • Topological Polar Surface Area: 25.8

6-Bromo-2,5-dichloroquinazoline Pricemore >>

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Additional information on 6-Bromo-2,5-dichloroquinazoline

6-Bromo-2,5-dichloroquinazoline (CAS 1644663-98-8): A Versatile Building Block in Medicinal Chemistry and Material Science

6-Bromo-2,5-dichloroquinazoline (CAS 1644663-98-8) is a highly functionalized heterocyclic compound that has gained significant attention in pharmaceutical research and advanced material development. As a quinazoline derivative, this compound serves as a crucial intermediate in the synthesis of various bioactive molecules and functional materials. The presence of both bromo and chloro substituents at strategic positions makes it particularly valuable for cross-coupling reactions and nucleophilic aromatic substitutions, which are fundamental transformations in modern synthetic chemistry.

The molecular structure of 6-Bromo-2,5-dichloroquinazoline features a quinazoline core with halogen atoms at positions 2, 5, and 6. This specific substitution pattern enables selective functionalization at multiple sites, making it a versatile building block for drug discovery programs. Researchers particularly value this compound for its ability to participate in palladium-catalyzed reactions, including Suzuki-Miyaura couplings and Buchwald-Hartwig aminations, which are essential for creating diverse molecular architectures.

In pharmaceutical applications, 6-Bromo-2,5-dichloroquinazoline serves as a key precursor for developing kinase inhibitors, a class of compounds that has revolutionized cancer treatment in recent years. The compound's structural features allow medicinal chemists to explore various modifications that can enhance target selectivity and improve drug-like properties. Recent studies have demonstrated its utility in creating potential therapeutics for EGFR-related disorders, a hot topic in precision medicine approaches to oncology.

Beyond medicinal chemistry, 6-Bromo-2,5-dichloroquinazoline finds applications in material science, particularly in the development of organic electronic materials. The electron-deficient nature of the quinazoline core, combined with the halogen substituents, makes it suitable for constructing π-conjugated systems with tailored optoelectronic properties. Researchers are exploring its potential in OLED materials and organic semiconductors, addressing the growing demand for more efficient and sustainable electronic devices.

The synthesis of 6-Bromo-2,5-dichloroquinazoline typically involves sequential halogenation of the quinazoline scaffold under controlled conditions. Modern synthetic approaches focus on improving atom economy and reducing environmental impact, aligning with the principles of green chemistry. Recent advancements in flow chemistry techniques have shown promise for scaling up production while maintaining high purity standards, a critical factor for pharmaceutical applications.

Analytical characterization of 6-Bromo-2,5-dichloroquinazoline employs various techniques including NMR spectroscopy, mass spectrometry, and X-ray crystallography. These methods confirm the compound's structural integrity and purity, which are essential for reproducible results in downstream applications. The compound typically appears as a white to off-white crystalline powder with good stability under standard storage conditions.

From a commercial perspective, 6-Bromo-2,5-dichloroquinazoline has seen growing demand from contract research organizations and pharmaceutical companies engaged in drug discovery. Suppliers have responded by developing reliable synthetic routes and quality control protocols to meet the needs of the research community. Current market trends indicate increasing interest in custom synthesis services for specialized quinazoline derivatives, with this compound serving as a popular starting material.

Safety considerations for handling 6-Bromo-2,5-dichloroquinazoline follow standard laboratory practices for halogenated heterocycles. While not classified as highly hazardous, proper personal protective equipment should be used, including gloves and eye protection. The compound should be stored in a cool, dry place away from incompatible materials, with attention to proper chemical storage guidelines.

Recent scientific literature highlights several innovative applications of 6-Bromo-2,5-dichloroquinazoline derivatives. One notable area involves the development of fluorescent probes for biological imaging, leveraging the quinazoline core's photophysical properties. Another emerging application is in the design of metal-organic frameworks (MOFs) with potential uses in gas storage and separation technologies.

The future outlook for 6-Bromo-2,5-dichloroquinazoline appears promising, with ongoing research exploring its potential in proteolysis targeting chimeras (PROTACs) and other targeted protein degradation strategies. These cutting-edge approaches represent one of the most exciting developments in drug discovery, addressing previously "undruggable" targets. As synthetic methodologies continue to advance, we can expect to see broader applications of this versatile building block across multiple scientific disciplines.

For researchers working with 6-Bromo-2,5-dichloroquinazoline, it's important to stay updated on the latest synthetic protocols and application studies. Many scientific databases and specialized chemistry platforms now offer detailed information about this compound's properties, handling, and potential uses. Regular literature reviews can help identify new opportunities for applying this valuable intermediate in innovative research projects.

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