Cas no 55285-43-3 (2,6-Dichloro-3-methoxyaniline)

2,6-Dichloro-3-methoxyaniline is a halogenated aniline derivative with the molecular formula C7H7Cl2NO. This compound features a methoxy group at the 3-position and chlorine substituents at the 2- and 6-positions of the aniline ring, imparting unique electronic and steric properties. Its structural characteristics make it a valuable intermediate in organic synthesis, particularly for the preparation of agrochemicals, pharmaceuticals, and specialty dyes. The electron-withdrawing chlorine atoms enhance reactivity in electrophilic substitution reactions, while the methoxy group contributes to solubility and further functionalization potential. Its high purity and stability under standard conditions ensure consistent performance in synthetic applications. The compound's well-defined structure allows for precise control in the development of complex molecules.
2,6-Dichloro-3-methoxyaniline structure
2,6-Dichloro-3-methoxyaniline structure
Product Name:2,6-Dichloro-3-methoxyaniline
CAS No:55285-43-3
MF:C7H7Cl2NO
MW:192.042579889297
MDL:MFCD20694612
CID:1094647
PubChem ID:20513888
Update Time:2025-07-02

2,6-Dichloro-3-methoxyaniline Chemical and Physical Properties

Names and Identifiers

    • 2,6-Dichloro-3-methoxyaniline
    • DB-329670
    • HAIBRTRWRXXIDR-UHFFFAOYSA-N
    • SCHEMBL374322
    • 55285-43-3
    • EN300-2146360
    • 2,6-dichloro-3-methoxy-phenylamine
    • CS-0061895
    • AKOS022189246
    • AS-62848
    • 2,6-dichloro-3-methoxy-aniline
    • Benzenamine, 2,6-dichloro-3-methoxy-
    • A12632
    • MDL: MFCD20694612
    • Inchi: 1S/C7H7Cl2NO/c1-11-5-3-2-4(8)7(10)6(5)9/h2-3H,10H2,1H3
    • InChI Key: HAIBRTRWRXXIDR-UHFFFAOYSA-N
    • SMILES: ClC1C(=C(C=CC=1OC)Cl)N

Computed Properties

  • Exact Mass: 190.99061
  • Monoisotopic Mass: 190.9904692g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 1
  • Complexity: 134
  • 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: 2.5
  • Topological Polar Surface Area: 35.2?2

Experimental Properties

  • PSA: 35.25

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Additional information on 2,6-Dichloro-3-methoxyaniline

Professional Introduction to 2,6-Dichloro-3-methoxyaniline (CAS No. 55285-43-3)

2,6-Dichloro-3-methoxyaniline is a significant intermediate in the realm of organic synthesis and pharmaceutical development. With the CAS number 55285-43-3, this compound has garnered attention due to its versatile applications in the synthesis of various bioactive molecules. The presence of both chloro and methoxy substituents on the aniline backbone imparts unique reactivity, making it a valuable building block for further chemical transformations.

The compound's structure, characterized by a benzene ring substituted with two chlorine atoms at the 2- and 6-positions and a methoxy group at the 3-position, contributes to its role as a key precursor in multiple synthetic pathways. Its molecular formula, C?H?Cl?NO, reflects a balance of electronegative and hydrophobic elements, which influences its interactions with other molecular entities.

In recent years, 2,6-Dichloro-3-methoxyaniline has been extensively studied for its potential in pharmaceutical applications. Researchers have leveraged its structural features to develop novel compounds with therapeutic properties. For instance, derivatives of this molecule have been explored as intermediates in the synthesis of kinase inhibitors, which are crucial in targeting various forms of cancer. The chloro substituents facilitate nucleophilic aromatic substitution reactions, enabling the introduction of diverse functional groups that can modulate biological activity.

Moreover, the methoxy group at the 3-position enhances the compound's solubility and stability, making it more amenable to further chemical modifications. This characteristic has been particularly useful in designing prodrugs that require controlled release mechanisms. The ability to manipulate both electron-withdrawing and -donating groups on the aromatic ring allows for fine-tuning of physicochemical properties, such as lipophilicity and metabolic stability.

The synthesis of 2,6-Dichloro-3-methoxyaniline typically involves multi-step processes that begin with readily available aromatic precursors. Common synthetic routes include chlorination and methylation reactions, often employing palladium-catalyzed cross-coupling techniques for high selectivity and yield. These methods highlight the compound's importance as a synthetic intermediate, bridging simple starting materials to complex bioactive molecules.

Recent advancements in computational chemistry have further enhanced the understanding of 2,6-Dichloro-3-methoxyaniline's reactivity. Molecular modeling studies have revealed insights into how different substituents influence its electronic properties and interactions with biological targets. This knowledge has paved the way for more efficient drug discovery strategies, where virtual screening can rapidly identify promising candidates based on structural features similar to known active compounds.

In addition to pharmaceutical applications, 2,6-Dichloro-3-methoxyaniline finds utility in agrochemical research. Its derivatives have been investigated as potential herbicides and fungicides due to their ability to disrupt essential metabolic pathways in pests. The structural motifs present in this compound allow for interactions with biological enzymes that are not easily targeted by other classes of agrochemicals.

The environmental impact of synthesizing and using 2,6-Dichloro-3-methoxyaniline is also a topic of interest. Efforts are being made to develop greener synthetic routes that minimize waste and reduce reliance on hazardous reagents. Catalytic processes that employ recyclable materials or renewable energy sources are being explored as alternatives to traditional methods.

The future prospects for 2,6-Dichloro-3-methoxyaniline are promising, with ongoing research focusing on expanding its applications across multiple industries. As our understanding of molecular interactions deepens, new opportunities for utilizing this compound will emerge. Whether in drug development or agrochemical innovation, its unique structural features ensure that it remains a cornerstone of synthetic chemistry.

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