Cas no 1804707-00-3 (4-Chloro-6-(difluoromethyl)pyridine-3-sulfonyl chloride)

4-Chloro-6-(difluoromethyl)pyridine-3-sulfonyl chloride is a versatile intermediate in organic synthesis, particularly valued for its reactive sulfonyl chloride and chloro-substituted pyridine moieties. These functional groups enable its use in cross-coupling reactions, nucleophilic substitutions, and the synthesis of sulfonamides or sulfonate esters. The difluoromethyl group enhances its utility in medicinal chemistry by influencing metabolic stability and lipophilicity. This compound is suitable for constructing agrochemicals, pharmaceuticals, and specialty chemicals, offering precise reactivity for tailored molecular modifications. Its stability under controlled conditions ensures consistent performance in synthetic applications. Handling requires standard precautions for sulfonyl chlorides, including moisture avoidance.
4-Chloro-6-(difluoromethyl)pyridine-3-sulfonyl chloride structure
1804707-00-3 structure
Product Name:4-Chloro-6-(difluoromethyl)pyridine-3-sulfonyl chloride
CAS No:1804707-00-3
MF:C6H3Cl2F2NO2S
MW:262.061325311661
MDL:MFCD25479096
CID:4781877
Update Time:2025-07-16

4-Chloro-6-(difluoromethyl)pyridine-3-sulfonyl chloride Chemical and Physical Properties

Names and Identifiers

    • 4-Chloro-2-(difluoromethyl)pyridine-5-sulfonyl chloride
    • 4-Chloro-6-(difluoromethyl)pyridine-3-sulfonyl chloride
    • MDL: MFCD25479096
    • Inchi: 1S/C6H3Cl2F2NO2S/c7-3-1-4(6(9)10)11-2-5(3)14(8,12)13/h1-2,6H
    • InChI Key: OIBLUKDJJFFUIW-UHFFFAOYSA-N
    • SMILES: ClC1=CC(C(F)F)=NC=C1S(=O)(=O)Cl

Computed Properties

  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 2
  • Complexity: 293
  • XLogP3: 2.2
  • Topological Polar Surface Area: 55.4

4-Chloro-6-(difluoromethyl)pyridine-3-sulfonyl chloride Pricemore >>

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Additional information on 4-Chloro-6-(difluoromethyl)pyridine-3-sulfonyl chloride

Professional Introduction to 4-Chloro-6-(difluoromethyl)pyridine-3-sulfonyl chloride (CAS No. 1804707-00-3)

4-Chloro-6-(difluoromethyl)pyridine-3-sulfonyl chloride, with the CAS number 1804707-00-3, is a significant compound in the field of pharmaceutical and agrochemical research. This compound belongs to the class of pyridine derivatives, which are widely recognized for their diverse biological activities and potential applications in drug development. The presence of both chloro and difluoromethyl substituents in its molecular structure enhances its reactivity and makes it a valuable intermediate in synthetic chemistry.

The< strong>3-sulfonyl chloride functional group in the molecule is particularly noteworthy, as it serves as a versatile handle for further chemical modifications. This group can be readily converted into other functional moieties, such as amines or alcohols, through nucleophilic substitution reactions. Such flexibility is crucial in medicinal chemistry, where the ability to modify molecular structures is essential for optimizing pharmacological properties.

In recent years, there has been growing interest in pyridine-based compounds due to their role as key scaffolds in the development of novel therapeutic agents. For instance, studies have demonstrated that pyridine derivatives can exhibit potent activity against various targets, including enzymes and receptors involved in inflammatory responses, infectious diseases, and cancer. The< strong>4-chloro and< strong>6-(difluoromethyl) substituents are particularly important, as they can influence the electronic properties of the molecule and enhance its binding affinity to biological targets.

One of the most compelling applications of 4-Chloro-6-(difluoromethyl)pyridine-3-sulfonyl chloride is in the synthesis of kinase inhibitors. Kinases are enzymes that play a critical role in cell signaling pathways, and their dysregulation is often associated with various diseases, particularly cancer. By designing molecules that specifically inhibit kinase activity, researchers can develop drugs that modulate these pathways effectively. The< strong>3-sulfonyl chloride group provides a convenient entry point for constructing such inhibitors, allowing for further derivatization to achieve high selectivity and potency.

The< strong>difluoromethyl group is another key feature of this compound, as it has been shown to improve metabolic stability and binding affinity in drug candidates. This substituent can enhance the lipophilicity of a molecule while also increasing its resistance to metabolic degradation. These properties are highly desirable in pharmaceutical development, as they can lead to more effective and longer-lasting therapeutic agents.

In academic research, 4-Chloro-6-(difluoromethyl)pyridine-3-sulfonyl chloride has been utilized in various synthetic protocols aimed at developing novel heterocyclic compounds. For example, it serves as a precursor for constructing more complex pyridine derivatives through nucleophilic aromatic substitution or metal-catalyzed cross-coupling reactions. These methods allow chemists to explore new chemical space and discover molecules with unique biological activities.

The compound's utility extends beyond pharmaceuticals into the agrochemical sector. Pyridine derivatives are known for their role as intermediates in the synthesis of pesticides and herbicides. The< strong>4-chloro and< strong>6-(difluoromethyl) substituents contribute to the efficacy of these agrochemicals by enhancing their bioavailability and target specificity. By leveraging the reactivity of< strong>3-sulfonyl chloride, researchers can design molecules that effectively protect crops from pests while minimizing environmental impact.

The synthesis of 4-Chloro-6-(difluoromethyl)pyridine-3-sulfonyl chloride involves multi-step organic reactions that require careful optimization to ensure high yield and purity. Common synthetic routes include chlorination of pyridine precursors followed by sulfonylation using chlorosulfonic acid or its equivalents. The introduction of the< strong>difluoromethyl group typically employs fluorinating agents such as Selectfluor or DAST (diethylaminosulfur trifluoride). These reactions must be conducted under controlled conditions to prevent side products and ensure reproducibility.

In conclusion, 4-Chloro-6-(difluoromethyl)pyridine-3-sulfonyl chloride (CAS No. 1804707-00-3) is a versatile compound with significant applications in pharmaceutical and agrochemical research. Its unique molecular structure, featuring both chloro and difluoromethyl substituents along with a sulfonyl chloride functional group, makes it an invaluable intermediate for synthesizing biologically active molecules. The ongoing research into pyridine derivatives continues to uncover new possibilities for developing innovative therapeutic agents and sustainable agricultural solutions.

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