Cas no 1379303-54-4 (2,6-Dibromopyridine-3-carboxamide)

2,6-Dibromopyridine-3-carboxamide is a brominated pyridine derivative with a carboxamide functional group at the 3-position. This compound serves as a versatile intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and specialty chemicals. The dibromo substitution enhances its reactivity, making it suitable for further functionalization via cross-coupling reactions or nucleophilic substitutions. Its carboxamide group provides additional sites for derivatization, enabling the synthesis of complex heterocyclic structures. The compound's high purity and stability under standard conditions ensure reliable performance in research and industrial applications. It is commonly utilized in medicinal chemistry for the development of bioactive molecules due to its structural flexibility and compatibility with diverse reaction conditions.
2,6-Dibromopyridine-3-carboxamide structure
1379303-54-4 structure
Product Name:2,6-Dibromopyridine-3-carboxamide
CAS No:1379303-54-4
MF:C6H4Br2N2O
MW:279.916759490967
CID:1089023
PubChem ID:71721357
Update Time:2025-11-01

2,6-Dibromopyridine-3-carboxamide Chemical and Physical Properties

Names and Identifiers

    • 2,6-Dibromonicotinamide
    • 2,6-dibromopyridine-3-carboxamide
    • 1379303-54-4
    • CS-0100916
    • SCHEMBL4491552
    • 3-Pyridinecarboxamide, 2,6-dibromo-
    • BS-20884
    • DTXSID70856955
    • 2,6-Dibromopyridine-3-carboxamide
    • Inchi: 1S/C6H4Br2N2O/c7-4-2-1-3(6(9)11)5(8)10-4/h1-2H,(H2,9,11)
    • InChI Key: HOEIBCGSMFYTCT-UHFFFAOYSA-N
    • SMILES: BrC1C(C(N)=O)=CC=C(N=1)Br

Computed Properties

  • Exact Mass: 279.86699g/mol
  • Monoisotopic Mass: 277.86904g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 1
  • Complexity: 165
  • 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
  • XLogP3: 1.8
  • Topological Polar Surface Area: 56?2

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Additional information on 2,6-Dibromopyridine-3-carboxamide

Introduction to 2,6-Dibromopyridine-3-carboxamide (CAS No. 1379303-54-4)

2,6-Dibromopyridine-3-carboxamide is a specialized organic compound that has garnered significant attention in the field of pharmaceutical and agrochemical research due to its versatile structural properties. This compound, identified by the Chemical Abstracts Service Number (CAS No.) 1379303-54-4, serves as a crucial intermediate in the synthesis of various biologically active molecules. Its molecular structure, featuring both bromine substituents and a carboxamide functional group, makes it a valuable building block for medicinal chemists exploring novel therapeutic agents.

The significance of 2,6-dibromopyridine-3-carboxamide lies in its ability to undergo a wide range of chemical transformations, which are essential for developing new compounds with tailored biological activities. The presence of bromine atoms at the 2- and 6-positions enhances its reactivity, allowing for selective functionalization at other sites such as the 3-position carboxamide group. This characteristic is particularly useful in the synthesis of heterocyclic derivatives that exhibit potent pharmacological effects.

In recent years, 2,6-dibromopyridine-3-carboxamide has been extensively studied for its potential applications in drug discovery. Researchers have leveraged its structural framework to develop inhibitors targeting various disease pathways. For instance, studies have demonstrated its role in synthesizing compounds that modulate enzyme activity relevant to inflammatory and infectious diseases. The brominated pyridine core is particularly appealing due to its ability to interact with biological targets through halogen bonding, a non-covalent interaction that often enhances binding affinity.

One of the most compelling aspects of 2,6-dibromopyridine-3-carboxamide is its utility in generating libraries of compounds for high-throughput screening (HTS). The compound’s structural flexibility allows medicinal chemists to introduce diverse modifications while maintaining key pharmacophoric elements. This approach has led to the identification of several lead compounds with promising preclinical profiles. Furthermore, advances in synthetic methodologies have enabled more efficient and scalable production of this intermediate, making it more accessible for industrial applications.

The carboxamide group in 2,6-dibromopyridine-3-carboxamide is particularly noteworthy for its role in conferring solubility and metabolic stability to derived molecules. This feature is critical for developing drugs that can be effectively administered and metabolized within the body. Additionally, the bromine atoms provide handles for further chemical manipulation, allowing researchers to explore modifications such as Suzuki-Miyaura cross-coupling reactions or nucleophilic substitutions. These reactions are fundamental in constructing complex molecular architectures essential for drug development.

Recent publications highlight the use of 2,6-dibromopyridine-3-carboxamide in designing small-molecule inhibitors targeting protein-protein interactions (PPIs). PPIs are involved in numerous cellular processes and are often implicated in diseases such as cancer and neurodegeneration. By incorporating this compound into drug candidates, researchers aim to disrupt aberrant PPI networks that contribute to pathogenesis. The success of such efforts depends on fine-tuning the compound’s pharmacokinetic properties through structural optimization.

The agrochemical sector has also benefited from the applications of 2,6-dibromopyridine-3-carboxamide. Derivatives of this compound have shown efficacy as intermediates in synthesizing pesticides and herbicides with improved selectivity and environmental safety. The ability to modify its structure allows chemists to develop formulations that target specific pests while minimizing harm to non-target organisms. This aligns with global efforts to promote sustainable agricultural practices through innovative chemical solutions.

In conclusion, 2,6-dibromopyridine-3-carboxamide (CAS No. 1379303-54-4) is a multifaceted compound with broad applications across pharmaceuticals and agrochemicals. Its unique structural features enable diverse chemical transformations, making it an indispensable tool for synthetic chemists. As research continues to uncover new therapeutic targets and sustainable agricultural solutions, the demand for high-quality intermediates like this one is expected to grow. The ongoing development of novel synthetic routes and optimization strategies will further enhance its utility in future scientific endeavors.

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