Cas no 58584-82-0 (2,6-Dichloropyridine-3,5-dicarboxylic acid)

2,6-Dichloropyridine-3,5-dicarboxylic acid is a versatile heterocyclic compound featuring two carboxylic acid groups and two chlorine substituents on a pyridine ring. This structure imparts reactivity suitable for applications in pharmaceutical synthesis, agrochemical intermediates, and coordination chemistry. The dichloro substitution enhances electrophilic properties, facilitating nucleophilic aromatic substitution reactions, while the dicarboxylic acid functionality allows for further derivatization or metal chelation. Its high purity and stability make it a reliable building block for complex molecular frameworks. The compound is particularly valued in medicinal chemistry for constructing bioactive scaffolds due to its balanced reactivity and potential for selective functionalization.
2,6-Dichloropyridine-3,5-dicarboxylic acid structure
58584-82-0 structure
Product Name:2,6-Dichloropyridine-3,5-dicarboxylic acid
CAS No:58584-82-0
MF:C7H3Cl2NO4
MW:236.009020090103
CID:1095539
PubChem ID:824638
Update Time:2025-10-12

2,6-Dichloropyridine-3,5-dicarboxylic acid Chemical and Physical Properties

Names and Identifiers

    • 2,6-Dichloropyridine-3,5-dicarboxylic acid
    • 2,6-dichloro-3,5-pyridinedicarboxylic acid
    • 58584-82-0
    • AC-907/34126026
    • 2,6-dichloropyridine-3,5-dicarboxylicacid
    • DB-093508
    • Inchi: 1S/C7H3Cl2NO4/c8-4-2(6(11)12)1-3(7(13)14)5(9)10-4/h1H,(H,11,12)(H,13,14)
    • InChI Key: TXJMUXYEEVSJQV-UHFFFAOYSA-N
    • SMILES: ClC1C(C(=O)O)=CC(C(=O)O)=C(N=1)Cl

Computed Properties

  • Exact Mass: 234.9439130g/mol
  • Monoisotopic Mass: 234.9439130g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 2
  • Complexity: 236
  • 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: 87.5?2

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2,6-Dichloropyridine-3,5-dicarboxylic acid Related Literature

Additional information on 2,6-Dichloropyridine-3,5-dicarboxylic acid

Introduction to 2,6-Dichloropyridine-3,5-dicarboxylic acid (CAS No. 58584-82-0)

2,6-Dichloropyridine-3,5-dicarboxylic acid, identified by its Chemical Abstracts Service (CAS) number 58584-82-0, is a significant compound in the realm of organic chemistry and pharmaceutical research. This heterocyclic aromatic compound features a pyridine core substituted with two chlorine atoms at the 2- and 6-positions, and carboxylic acid groups at the 3- and 5-positions. Its unique structural framework makes it a valuable intermediate in the synthesis of various biologically active molecules.

The compound's molecular formula, C?H?Cl?NO?, underscores its complexity and potential reactivity. The presence of both chloro and carboxylic acid functional groups provides multiple sites for chemical modification, enabling the development of diverse derivatives with tailored properties. This versatility has garnered considerable attention from researchers exploring novel pharmacophores and therapeutic agents.

In recent years, 2,6-Dichloropyridine-3,5-dicarboxylic acid has been increasingly utilized in the synthesis of advanced materials and pharmaceuticals. One notable application lies in its role as a precursor for constructing complex organic frameworks. These frameworks are of particular interest in drug discovery due to their ability to mimic natural product scaffolds and exhibit promising biological activities.

Recent studies have highlighted the compound's utility in developing inhibitors targeting specific enzymatic pathways. For instance, derivatives of 2,6-Dichloropyridine-3,5-dicarboxylic acid have shown promise in inhibiting enzymes involved in inflammatory responses and cancer progression. The carboxylic acid groups facilitate hydrogen bonding interactions with biological targets, enhancing binding affinity and specificity.

The chloro substituents on the pyridine ring contribute to the compound's lipophilicity, which is often critical for membrane permeability and bioavailability of pharmaceuticals. This balance between hydrophilic and lipophilic characteristics makes 2,6-Dichloropyridine-3,5-dicarboxylic acid an attractive building block for designing orally active drugs.

In addition to its pharmaceutical applications, this compound has found utility in agrochemical research. Researchers have explored its derivatives as potential herbicides and fungicides due to their ability to disrupt essential metabolic pathways in pests. The structural diversity offered by 2,6-Dichloropyridine-3,5-dicarboxylic acid allows for the creation of compounds with high selectivity toward specific targets.

The synthesis of 2,6-Dichloropyridine-3,5-dicarboxylic acid typically involves multi-step organic transformations starting from commercially available pyridine derivatives. Advanced synthetic methodologies have been developed to improve yield and purity while minimizing environmental impact. Techniques such as catalytic chlorination and selective carboxylation are commonly employed in its preparation.

The compound's stability under various conditions has also been a focus of research. Studies have demonstrated that proper storage conditions can significantly enhance its shelf life and reactivity. This is particularly important for industrial applications where consistent quality is paramount.

Efforts to optimize the synthesis of 2,6-Dichloropyridine-3,5-dicarboxylic acid have led to greener alternatives that reduce reliance on hazardous reagents. Recent innovations in flow chemistry have enabled more efficient production processes with reduced waste generation. These advancements align with global trends toward sustainable chemical manufacturing.

The growing interest in heterocyclic compounds like 2,6-Dichloropyridine-3,5-dicarboxylic acid reflects their immense potential in addressing unmet medical needs. Ongoing research continues to uncover new derivatives with enhanced pharmacological properties. Collaborative efforts between academia and industry are crucial for translating these findings into tangible therapeutic solutions.

The future prospects for this compound are promising as new synthetic routes are explored and novel applications are discovered. Its role as a key intermediate ensures continued relevance in both academic research and industrial development pipelines.

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