Cas no 1805959-14-1 (2-Amino-3-chloro-6-(difluoromethyl)pyridine)

2-Amino-3-chloro-6-(difluoromethyl)pyridine is a halogenated pyridine derivative with significant utility in agrochemical and pharmaceutical synthesis. Its structural features, including the difluoromethyl group and chloro-substitution, enhance reactivity and selectivity, making it a valuable intermediate for constructing complex molecules. The amino group provides a versatile handle for further functionalization, enabling the development of targeted compounds. This compound exhibits stability under standard conditions, ensuring reliable handling and storage. Its applications include the synthesis of herbicides and bioactive molecules, where its unique substitution pattern contributes to improved efficacy and metabolic stability. The product is characterized by high purity and consistent quality, meeting rigorous industry standards.
2-Amino-3-chloro-6-(difluoromethyl)pyridine structure
1805959-14-1 structure
Product Name:2-Amino-3-chloro-6-(difluoromethyl)pyridine
CAS No:1805959-14-1
MF:C6H5ClF2N2
MW:178.567106962204
CID:4925910
Update Time:2025-05-26

2-Amino-3-chloro-6-(difluoromethyl)pyridine Chemical and Physical Properties

Names and Identifiers

    • 3-chloro-6-(difluoromethyl)pyridin-2-amine
    • 2-Amino-3-chloro-6-(difluoromethyl)pyridine
    • Inchi: 1S/C6H5ClF2N2/c7-3-1-2-4(5(8)9)11-6(3)10/h1-2,5H,(H2,10,11)
    • InChI Key: SDBDDHRAXCUNLO-UHFFFAOYSA-N
    • SMILES: ClC1C=CC(C(F)F)=NC=1N

Computed Properties

  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 1
  • Complexity: 134
  • XLogP3: 1.8
  • Topological Polar Surface Area: 38.9

2-Amino-3-chloro-6-(difluoromethyl)pyridine Pricemore >>

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Additional information on 2-Amino-3-chloro-6-(difluoromethyl)pyridine

Introduction to 2-Amino-3-chloro-6-(difluoromethyl)pyridine (CAS No. 1805959-14-1)

2-Amino-3-chloro-6-(difluoromethyl)pyridine, identified by the Chemical Abstracts Service Number (CAS No.) 1805959-14-1, is a significant compound in the realm of pharmaceutical and agrochemical research. This heterocyclic aromatic amine features a pyridine core substituted with an amino group at the 2-position, a chloro group at the 3-position, and a difluoromethyl group at the 6-position. The unique structural arrangement of these substituents imparts distinct chemical properties, making it a valuable intermediate in synthetic chemistry and a promising candidate for developing novel bioactive molecules.

The compound's molecular structure, characterized by its electron-withdrawing and electron-donating groups, influences its reactivity and interaction with biological targets. The presence of the amino group enhances its potential for further functionalization, while the chloro and difluoromethyl substituents contribute to its stability and metabolic resistance. These attributes make 2-Amino-3-chloro-6-(difluoromethyl)pyridine a versatile building block for medicinal chemists seeking to design molecules with enhanced pharmacological profiles.

In recent years, there has been growing interest in pyridine derivatives due to their broad spectrum of biological activities. Research has demonstrated that such compounds exhibit inhibitory effects on various enzymes and receptors, making them relevant in the development of drugs targeting neurological disorders, infectious diseases, and cancer. Specifically, derivatives of this class have shown promise in preclinical studies as kinase inhibitors and antimicrobial agents.

One of the most compelling aspects of 2-Amino-3-chloro-6-(difluoromethyl)pyridine is its role in the synthesis of small-molecule inhibitors that modulate protein-protein interactions. The pyridine ring serves as a scaffold that can be modified to achieve high specificity for target proteins. For instance, studies have highlighted its utility in creating inhibitors of Janus kinases (JAKs), which are involved in inflammatory signaling pathways. The incorporation of the difluoromethyl group has been particularly noted for its ability to improve binding affinity and reduce metabolic clearance, thereby enhancing drug efficacy.

The agrochemical sector has also benefited from the exploration of pyridine-based compounds. 2-Amino-3-chloro-6-(difluoromethyl)pyridine has been employed in the synthesis of novel herbicides and fungicides that exhibit improved environmental compatibility while maintaining high efficacy against pests and pathogens. The structural features of this compound allow for fine-tuning of its biological activity, enabling researchers to develop products with targeted modes of action.

Advances in computational chemistry have further accelerated the discovery process for derivatives of 2-Amino-3-chloro-6-(difluoromethyl)pyridine. Molecular modeling techniques predict how different substituents will influence the compound's interactions with biological targets, guiding synthetic efforts toward more potent and selective molecules. This interdisciplinary approach combines experimental synthesis with theoretical analysis to streamline drug development pipelines.

The synthesis of 2-Amino-3-chloro-6-(difluoromethyl)pyridine itself presents interesting challenges due to the need for precise regioselectivity during functionalization. Researchers have developed innovative synthetic routes that leverage transition metal catalysis and organometallic chemistry to construct the desired framework efficiently. These methodologies not only improve yield but also minimize byproduct formation, aligning with green chemistry principles.

Recent patents have emerged that detail novel applications for 2-Amino-3-chloro-6-(difluoromethyl)pyridine in therapeutic areas such as antiviral and anti-inflammatory treatments. For example, modifications to this core structure have yielded compounds that disrupt viral replication mechanisms or inhibit inflammatory cytokines. Such findings underscore the compound's versatility as a starting point for drug discovery initiatives.

The regulatory landscape for new chemical entities like 2-Amino-3-chloro-6-(difluoromethyl)pyridine continues to evolve, emphasizing safety and environmental considerations without stifling innovation. Manufacturers must navigate stringent guidelines while ensuring that their processes are sustainable and scalable for commercial production. This balance is critical for bringing promising candidates from laboratory research to market-ready pharmaceuticals or agrochemicals.

Looking ahead, the future research directions for 2-Amino-3-chloro-6-(difluoromethyl)pyridine may include exploring its potential in photopharmacology—where light activation can modulate drug activity—and its incorporation into prodrug formulations that enhance bioavailability or targeted delivery systems. The compound's unique structural features make it an attractive candidate for these emerging fields.

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