Cas no 1227493-80-2 (2-Bromo-4-(chloromethyl)-5-fluoropyridine)

2-Bromo-4-(chloromethyl)-5-fluoropyridine is a halogenated pyridine derivative with significant utility in pharmaceutical and agrochemical synthesis. Its key structural features—a bromo substituent at the 2-position, a chloromethyl group at the 4-position, and a fluorine atom at the 5-position—make it a versatile intermediate for nucleophilic substitution and cross-coupling reactions. The presence of multiple reactive sites allows for selective functionalization, enabling the construction of complex heterocyclic frameworks. This compound is particularly valuable in medicinal chemistry for the development of bioactive molecules due to its ability to introduce both halogen and fluorinated motifs. High purity and stability under standard conditions further enhance its applicability in industrial and research settings.
2-Bromo-4-(chloromethyl)-5-fluoropyridine structure
1227493-80-2 structure
Product Name:2-Bromo-4-(chloromethyl)-5-fluoropyridine
CAS No:1227493-80-2
MF:C6H4BrClFN
MW:224.45806312561
CID:4733107
PubChem ID:122455878
Update Time:2025-09-28

2-Bromo-4-(chloromethyl)-5-fluoropyridine Chemical and Physical Properties

Names and Identifiers

    • 2-Bromo-4-(chloromethyl)-5-fluoropyridine
    • UXKDZNGVWGODSY-UHFFFAOYSA-N
    • Inchi: 1S/C6H4BrClFN/c7-6-1-4(2-8)5(9)3-10-6/h1,3H,2H2
    • InChI Key: UXKDZNGVWGODSY-UHFFFAOYSA-N
    • SMILES: BrC1C=C(CCl)C(=CN=1)F

Computed Properties

  • Exact Mass: 222.91997g/mol
  • Monoisotopic Mass: 222.91997g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 1
  • Complexity: 114
  • 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
  • Topological Polar Surface Area: 12.9
  • XLogP3: 2.4

2-Bromo-4-(chloromethyl)-5-fluoropyridine Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
CHENG DOU FEI BO YI YAO Technology Co., Ltd.
FD01643-5g
2-bromo-4-(chloromethyl)-5-fluoropyridine
1227493-80-2 95%
5g
$2200 2023-09-07
SHANG HAI HAO HONG Biomedical Technology Co., Ltd.
1762634-1g
2-Bromo-4-(chloromethyl)-5-fluoropyridine
1227493-80-2 98%
1g
¥4630.00 2024-08-09

Additional information on 2-Bromo-4-(chloromethyl)-5-fluoropyridine

Introduction to 2-Bromo-4-(chloromethyl)-5-fluoropyridine (CAS No: 1227493-80-2)

2-Bromo-4-(chloromethyl)-5-fluoropyridine, identified by its Chemical Abstracts Service (CAS) number 1227493-80-2, is a fluorinated pyridine derivative that has garnered significant attention in the field of pharmaceutical and agrochemical research. This compound serves as a versatile intermediate in the synthesis of various bioactive molecules, particularly in the development of novel therapeutic agents. Its unique structural features, including the presence of both bromo and chloromethyl substituents, make it a valuable building block for further functionalization and derivatization.

The fluoropyridine core is a well-documented pharmacophore in medicinal chemistry, known for its ability to enhance metabolic stability, binding affinity, and overall pharmacological activity. The introduction of fluorine at the 5-position further modulates these properties, making such derivatives particularly attractive for drug discovery. In recent years, there has been a surge in research focusing on fluorinated heterocycles due to their promising biological profiles. For instance, studies have demonstrated that fluorine atoms can influence electronic effects, lipophilicity, and binding interactions with biological targets, thereby fine-tuning the pharmacokinetic and pharmacodynamic properties of drug candidates.

2-Bromo-4-(chloromethyl)-5-fluoropyridine is particularly interesting because it combines multiple reactive sites that can be selectively modified. The bromo group at the 2-position allows for further substitution via cross-coupling reactions such as Suzuki-Miyaura or Buchwald-Hartwig couplings, enabling the introduction of aryl or amino groups. Concurrently, the chloromethyl moiety at the 4-position provides a site for nucleophilic addition reactions, allowing for the incorporation of alcohols or amines. This dual reactivity makes it an invaluable intermediate in constructing complex molecular architectures.

Recent advancements in synthetic methodologies have expanded the utility of 2-Bromo-4-(chloromethyl)-5-fluoropyridine in drug discovery pipelines. For example, researchers have leveraged this compound to develop kinase inhibitors, which are critical in treating cancers and inflammatory diseases. The pyridine scaffold is frequently found in kinase inhibitors due to its ability to mimic ATP binding pockets and disrupt enzyme activity. By incorporating fluorine and halogenated functional groups, chemists can optimize binding interactions with target kinases while minimizing off-target effects.

In addition to its applications in oncology, 2-Bromo-4-(chloromethyl)-5-fluoropyridine has shown promise in the development of antimicrobial agents. The increasing prevalence of drug-resistant pathogens has necessitated the discovery of novel antibiotics with unique mechanisms of action. Fluorinated pyridines have been explored as key structural elements in antibiotics due to their ability to enhance bacterial cell wall penetration and disrupt essential metabolic pathways. The presence of bromo and chloromethyl groups allows for further derivatization into compounds that exhibit potent antibacterial activity while maintaining favorable pharmacokinetic profiles.

The agrochemical sector has also benefited from the versatility of 2-Bromo-4-(chloromethyl)-5-fluoropyridine. Pyridine derivatives are widely used as intermediates in the synthesis of herbicides, fungicides, and insecticides. The introduction of fluorine atoms often enhances the environmental stability and bioavailability of agrochemicals, ensuring their efficacy in field conditions. Researchers have reported successful applications of this compound in developing next-generation crop protection agents that offer improved performance while adhering to stringent environmental regulations.

From a synthetic chemistry perspective, 2-Bromo-4-(chloromethyl)-5-fluoropyridine exemplifies the importance of functional group diversity in medicinal chemistry. The ability to selectively modify both bromo and chloromethyl sites enables chemists to explore a wide range of chemical space, leading to the discovery of novel bioactive molecules. Techniques such as palladium-catalyzed cross-coupling reactions have been particularly instrumental in transforming this intermediate into structurally diverse libraries for high-throughput screening.

The growing interest in fluorinated pyridines is also driven by their potential applications in material science and electronics. Fluorinated heterocycles are known for their electron-withdrawing properties and high thermal stability, making them suitable candidates for organic semiconductors and liquid crystal displays (LCDs). While these applications are less directly related to pharmaceuticals, they underscore the broad utility of fluorinated compounds across multiple scientific disciplines.

In conclusion,2-Bromo-4-(chloromethyl)-5-fluoropyridine (CAS No: 1227493-80-2) is a multifaceted compound with significant implications in pharmaceutical research, agrochemical development, and material science. Its unique structural features and reactivity make it an indispensable tool for chemists seeking to design novel bioactive molecules with optimized pharmacological properties. As research continues to uncover new applications for fluorinated pyridines,this compound is poised to remain at the forefront of chemical innovation.

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