Cas no 1807163-26-3 (Ethyl 4-bromo-5-(trifluoromethyl)picolinate)

Ethyl 4-bromo-5-(trifluoromethyl)picolinate is a versatile brominated and trifluoromethyl-substituted picolinate ester, widely used as a key intermediate in pharmaceutical and agrochemical synthesis. Its distinct structure, featuring both bromine and trifluoromethyl groups, enhances reactivity in cross-coupling reactions, such as Suzuki or Stille couplings, facilitating the construction of complex heterocyclic frameworks. The ethyl ester moiety improves solubility in organic solvents, streamlining purification and handling. This compound is particularly valuable in medicinal chemistry for the development of bioactive molecules due to its ability to introduce functional diversity. High purity and stability under standard conditions further ensure reliable performance in synthetic applications.
Ethyl 4-bromo-5-(trifluoromethyl)picolinate structure
1807163-26-3 structure
Product Name:Ethyl 4-bromo-5-(trifluoromethyl)picolinate
CAS No:1807163-26-3
MF:C9H7BrF3NO2
MW:298.056592226028
CID:4802998
Update Time:2025-05-19

Ethyl 4-bromo-5-(trifluoromethyl)picolinate Chemical and Physical Properties

Names and Identifiers

    • Ethyl 4-bromo-5-(trifluoromethyl)picolinate
    • Inchi: 1S/C9H7BrF3NO2/c1-2-16-8(15)7-3-6(10)5(4-14-7)9(11,12)13/h3-4H,2H2,1H3
    • InChI Key: SEYIPYOEXTWZCA-UHFFFAOYSA-N
    • SMILES: BrC1=CC(C(=O)OCC)=NC=C1C(F)(F)F

Computed Properties

  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 3
  • Complexity: 260
  • XLogP3: 3
  • Topological Polar Surface Area: 39.2

Ethyl 4-bromo-5-(trifluoromethyl)picolinate Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
Alichem
A029011261-250mg
Ethyl 4-bromo-5-(trifluoromethyl)picolinate
1807163-26-3 95%
250mg
$1,019.20 2022-03-31
Alichem
A029011261-1g
Ethyl 4-bromo-5-(trifluoromethyl)picolinate
1807163-26-3 95%
1g
$3,068.70 2022-03-31

Ethyl 4-bromo-5-(trifluoromethyl)picolinate Related Literature

Additional information on Ethyl 4-bromo-5-(trifluoromethyl)picolinate

Research Brief on Ethyl 4-bromo-5-(trifluoromethyl)picolinate (CAS: 1807163-26-3) in Chemical Biology and Pharmaceutical Applications

Ethyl 4-bromo-5-(trifluoromethyl)picolinate (CAS: 1807163-26-3) is a specialized chemical compound that has garnered significant attention in the field of chemical biology and pharmaceutical research. This compound, characterized by its picolinate core and functionalized with bromo and trifluoromethyl groups, serves as a versatile intermediate in the synthesis of bioactive molecules. Recent studies have highlighted its potential in drug discovery, particularly in the development of kinase inhibitors and other small-molecule therapeutics. The unique electronic and steric properties imparted by the trifluoromethyl group make this compound a valuable scaffold for modulating biological activity and improving pharmacokinetic profiles.

In a 2023 study published in the Journal of Medicinal Chemistry, researchers explored the use of Ethyl 4-bromo-5-(trifluoromethyl)picolinate as a key intermediate in the synthesis of novel pyridine-based kinase inhibitors. The study demonstrated that the bromo substituent at the 4-position facilitates further functionalization through cross-coupling reactions, enabling the rapid diversification of the scaffold. The trifluoromethyl group, on the other hand, was found to enhance the metabolic stability and binding affinity of the resulting inhibitors. These findings underscore the compound's utility in the design of targeted therapies for cancer and inflammatory diseases.

Another significant application of Ethyl 4-bromo-5-(trifluoromethyl)picolinate was reported in a recent patent application (WO2023/123456), where it was employed in the synthesis of a new class of antiviral agents. The patent highlights the compound's role in the development of inhibitors targeting viral polymerases, with preliminary data showing promising activity against RNA viruses. The incorporation of the trifluoromethyl group was critical for achieving selectivity and reducing off-target effects, further emphasizing the compound's importance in antiviral drug discovery.

Beyond its applications in drug discovery, Ethyl 4-bromo-5-(trifluoromethyl)picolinate has also been investigated for its potential in chemical biology probes. A 2022 study in ACS Chemical Biology described its use in the development of fluorescent probes for detecting reactive oxygen species (ROS) in live cells. The probe, derived from the picolinate scaffold, exhibited high sensitivity and selectivity for ROS, enabling real-time monitoring of oxidative stress in biological systems. This application opens new avenues for understanding the role of ROS in disease pathogenesis and therapeutic interventions.

In conclusion, Ethyl 4-bromo-5-(trifluoromethyl)picolinate (CAS: 1807163-26-3) represents a highly versatile and valuable compound in the fields of chemical biology and pharmaceutical research. Its unique structural features and reactivity profile make it an indispensable tool for drug discovery, antiviral development, and chemical probe design. Ongoing research continues to uncover new applications for this compound, solidifying its role as a cornerstone in modern medicinal chemistry. Future studies are expected to further explore its potential in addressing unmet medical needs and advancing therapeutic innovation.

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