Cas no 1805238-19-0 (2-Bromo-3-chloro-6-(difluoromethyl)-4-(trifluoromethyl)pyridine)

2-Bromo-3-chloro-6-(difluoromethyl)-4-(trifluoromethyl)pyridine is a halogenated pyridine derivative with a unique substitution pattern, offering versatile reactivity for synthetic applications. The presence of bromo and chloro groups at the 2- and 3-positions enhances its utility as a building block in cross-coupling reactions, while the difluoromethyl and trifluoromethyl groups at the 6- and 4-positions contribute to its electron-withdrawing properties and potential bioactivity. This compound is particularly valuable in agrochemical and pharmaceutical research, where fluorinated pyridines are often employed to modulate physicochemical properties. Its structural features make it a promising intermediate for the development of advanced functional materials and active ingredients.
2-Bromo-3-chloro-6-(difluoromethyl)-4-(trifluoromethyl)pyridine structure
1805238-19-0 structure
Product Name:2-Bromo-3-chloro-6-(difluoromethyl)-4-(trifluoromethyl)pyridine
CAS No:1805238-19-0
MF:C7H2BrClF5N
MW:310.446497440338
CID:4810232
Update Time:2025-10-28

2-Bromo-3-chloro-6-(difluoromethyl)-4-(trifluoromethyl)pyridine Chemical and Physical Properties

Names and Identifiers

    • 2-Bromo-3-chloro-6-(difluoromethyl)-4-(trifluoromethyl)pyridine
    • Inchi: 1S/C7H2BrClF5N/c8-5-4(9)2(7(12,13)14)1-3(15-5)6(10)11/h1,6H
    • InChI Key: HNNDZCKWILKVEP-UHFFFAOYSA-N
    • SMILES: BrC1=C(C(C(F)(F)F)=CC(C(F)F)=N1)Cl

Computed Properties

  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 1
  • Complexity: 224
  • XLogP3: 4
  • Topological Polar Surface Area: 12.9

2-Bromo-3-chloro-6-(difluoromethyl)-4-(trifluoromethyl)pyridine Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
Alichem
A029063296-1g
2-Bromo-3-chloro-6-(difluoromethyl)-4-(trifluoromethyl)pyridine
1805238-19-0 97%
1g
$1,475.10 2022-04-01

Additional information on 2-Bromo-3-chloro-6-(difluoromethyl)-4-(trifluoromethyl)pyridine

Introduction to 2-Bromo-3-chloro-6-(difluoromethyl)-4-(trifluoromethyl)pyridine (CAS No. 1805238-19-0)

2-Bromo-3-chloro-6-(difluoromethyl)-4-(trifluoromethyl)pyridine (CAS No. 1805238-19-0) is a highly specialized heterocyclic compound that has garnered significant attention in the field of pharmaceutical chemistry and medicinal research. This compound, characterized by its bromo and chloro substituents along with two fluorinated methyl groups, represents a unique structural motif that is often employed in the synthesis of biologically active molecules. The presence of multiple fluorine atoms enhances its lipophilicity and metabolic stability, making it an attractive scaffold for drug development.

The structure of this pyridine derivative is meticulously designed to optimize interactions with biological targets, particularly enzymes and receptors involved in critical metabolic pathways. The bromo and chloro atoms serve as versatile handles for further functionalization, enabling chemists to introduce additional pharmacophores or modify existing ones. This flexibility is crucial in the iterative process of drug discovery, where subtle structural changes can significantly alter biological activity.

In recent years, the pharmaceutical industry has increasingly focused on developing small molecules with enhanced binding affinity and selectivity. 2-Bromo-3-chloro-6-(difluoromethyl)-4-(trifluoromethyl)pyridine exemplifies this trend, as its fluorinated substituents contribute to strong π-stacking interactions and improved pharmacokinetic properties. Such features are particularly valuable in the design of kinase inhibitors, which play a pivotal role in treating cancers and inflammatory diseases.

One of the most compelling aspects of this compound is its potential application in the development of antiviral agents. The pyridine core is a common structural element in many antiviral drugs, where it interacts with viral proteases or polymerases. The introduction of halogenated and fluorinated groups into this core can modulate binding affinity and resistance profiles, making it an ideal candidate for next-generation antiviral therapies. Recent studies have demonstrated that analogs of this compound exhibit promising activity against RNA viruses by inhibiting key replication enzymes.

The synthesis of 2-Bromo-3-chloro-6-(difluoromethyl)-4-(trifluoromethyl)pyridine typically involves multi-step organic reactions, often starting from commercially available pyridine precursors. Key steps include halogenation at specific positions, followed by fluorination using appropriate reagents such as Selectfluor or DAST (diethylaminosulfur trifluoride). The precise regioselectivity achieved during these transformations is critical to obtaining the desired product with minimal side reactions.

The spectroscopic properties of this compound are also noteworthy. Nuclear magnetic resonance (NMR) spectroscopy reveals distinct chemical shifts for the various protons and carbons, allowing for unambiguous structural confirmation. Mass spectrometry (MS) further confirms the molecular weight and fragmentation patterns consistent with the proposed structure. These analytical techniques are essential for ensuring the purity and identity of the compound before it is used in downstream applications.

From a medicinal chemistry perspective, the bioisosteric replacement of hydrogen atoms with halogens or fluorines is a well-established strategy to improve drug properties. In 2-Bromo-3-chloro-6-(difluoromethyl)-4-(trifluoromethyl)pyridine, this approach has been taken to extremes, with three halogen atoms and two fluorine atoms replacing hydrogens on the pyridine ring. This high degree of substitution not only enhances binding interactions but also confers resistance to metabolic degradation by enzymes such as cytochrome P450 oxidases.

The pharmacological profile of this compound has been explored in several preclinical studies. In vitro assays have shown that derivatives of this scaffold exhibit potent inhibition against various kinases, including those overexpressed in cancer cells. Additionally, preliminary animal models suggest that these compounds may have favorable pharmacokinetic profiles, including good oral bioavailability and reduced off-target effects. These findings make it a promising candidate for further development into novel therapeutic agents.

The role of fluorinated compounds in modern medicine cannot be overstated. Their unique electronic properties allow them to interact strongly with biological targets while remaining stable under physiological conditions. The widespread use of fluorine in drug development underscores its importance as a key structural element in medicinal chemistry. Compounds like 2-Bromo-3-chloro-6-(difluoromethyl)-4-(trifluoromethyl)pyridine continue to push the boundaries of what is possible in terms of molecular design and therapeutic efficacy.

In conclusion, 2-Bromo-3-chloro-6-(difluoromethyl)-4-(trifluoromethyl)pyridine (CAS No. 1805238-19-0) represents a cutting-edge chemical entity with significant potential in pharmaceutical research. Its unique structural features make it an invaluable tool for synthesizing novel bioactive molecules, particularly those targeting viral infections and cancers. As research continues to uncover new applications for halogenated pyridines, compounds like this will undoubtedly play a central role in shaping the future of drug discovery and development.

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