Cas no 56680-89-8 (3,5-dichloro-2-methoxyphenol)

3,5-Dichloro-2-methoxyphenol is a chlorinated phenolic compound characterized by its methoxy and dichloro substituents on the aromatic ring. This structure imparts distinct chemical properties, including enhanced stability and reactivity, making it valuable as an intermediate in organic synthesis. Its electron-withdrawing groups facilitate selective reactions, particularly in the production of agrochemicals, pharmaceuticals, and specialty chemicals. The compound's high purity and well-defined molecular structure ensure consistent performance in synthetic applications. It is typically handled under controlled conditions due to its potential reactivity, requiring appropriate safety measures. Its utility lies in its role as a versatile building block for constructing complex molecules with precision.
3,5-dichloro-2-methoxyphenol structure
3,5-dichloro-2-methoxyphenol structure
Product Name:3,5-dichloro-2-methoxyphenol
CAS No:56680-89-8
MF:C7H6Cl2O2
MW:193.02734041214
MDL:MFCD02751970
CID:372726
PubChem ID:92353
Update Time:2025-10-28

3,5-dichloro-2-methoxyphenol Chemical and Physical Properties

Names and Identifiers

    • Phenol,3,5-dichloro-2-methoxy-
    • 3,5-Dichloro-2-methoxyphenol
    • 3,5-Dichloroguaicol
    • CCRIS 4057
    • SCHEMBL9332735
    • 3,5-Dichloro-guaiacol
    • EINECS 260-333-4
    • 56680-89-8
    • YFKQRZRAQLZDAZ-UHFFFAOYSA-N
    • 3,5-Dichloro-2-methoxyphenol #
    • Phenol, 3,5-dichloro-2-methoxy-
    • NS00033564
    • EN300-1984402
    • DTXSID10205241
    • 3,5-dichloro-2-methoxyphenol
    • MDL: MFCD02751970
    • Inchi: 1S/C7H6Cl2O2/c1-11-7-5(9)2-4(8)3-6(7)10/h2-3,10H,1H3
    • InChI Key: YFKQRZRAQLZDAZ-UHFFFAOYSA-N
    • SMILES: ClC1=CC(=CC(=C1OC)O)Cl

Computed Properties

  • Exact Mass: 191.97458
  • Monoisotopic Mass: 191.9744848g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 1
  • Complexity: 132
  • 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: 3.1
  • Topological Polar Surface Area: 29.5?2

Experimental Properties

  • PSA: 29.46

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Additional information on 3,5-dichloro-2-methoxyphenol

Introduction to 3,5-dichloro-2-methoxyphenol (CAS No. 56680-89-8)

3,5-dichloro-2-methoxyphenol, identified by the Chemical Abstracts Service Number (CAS No.) 56680-89-8, is a significant organic compound that has garnered considerable attention in the field of pharmaceutical chemistry and agrochemical research. This compound, characterized by its chloro and methoxy substituents on a phenolic ring, exhibits unique chemical properties that make it a valuable intermediate in the synthesis of various bioactive molecules.

The structural motif of 3,5-dichloro-2-methoxyphenol consists of a benzene ring substituted with two chlorine atoms at the 3rd and 5th positions, and a methoxy group at the 2nd position. This specific arrangement imparts distinct reactivity patterns, making it a versatile building block for further functionalization. The presence of both electron-withdrawing chloro groups and an electron-donating methoxy group creates a balance of electronic effects that influences its interactions with biological targets.

In recent years, 3,5-dichloro-2-methoxyphenol has been extensively studied for its potential applications in medicinal chemistry. Its structural features allow for facile modifications, enabling the development of novel compounds with therapeutic properties. Researchers have explored its utility in synthesizing derivatives with antimicrobial, anti-inflammatory, and anticancer activities. The compound’s ability to serve as a precursor for more complex molecules has made it a focal point in drug discovery initiatives.

One of the most compelling aspects of 3,5-dichloro-2-methoxyphenol is its role in the development of agrochemicals. The phenolic core and halogen substituents contribute to its efficacy as a herbicide or fungicide. Current studies are investigating its derivatives as environmentally sustainable alternatives to conventional agrochemicals, emphasizing the need for compounds that offer high potency while minimizing ecological impact.

The synthesis of 3,5-dichloro-2-methoxyphenol typically involves chlorination and methylation reactions on an appropriate aromatic precursor. Advances in synthetic methodologies have enabled more efficient and scalable production processes, reducing costs and improving yields. These advancements are crucial for ensuring the availability of this compound for industrial applications.

From a mechanistic standpoint, 3,5-dichloro-2-methoxyphenol participates in various chemical transformations due to its reactive sites. The hydroxyl group can engage in esterification or etherification reactions, while the chloro groups can undergo nucleophilic aromatic substitution or metal-catalyzed cross-coupling reactions. Such reactivity makes it an indispensable tool in organic synthesis laboratories.

The pharmacological potential of 3,5-dichloro-2-methoxyphenol has been further explored through computational modeling and high-throughput screening assays. These approaches have identified promising lead structures derived from this compound that exhibit inhibitory activity against key biological targets. For instance, derivatives have shown promise in disrupting enzyme pathways involved in cancer progression or modulating immune responses.

In addition to pharmaceutical applications, 3,5-dichloro-2-methoxyphenol finds utility in material science. Its ability to form coordination complexes with metal ions has led to investigations into its use as a ligand in catalytic systems or as a component in functional materials. The interplay between its electronic structure and metal binding capabilities offers exciting opportunities for innovation.

The environmental impact of using 3,5-dichloro-2-methoxyphenol must be carefully considered alongside its benefits. While it offers significant advantages in synthetic chemistry and bioactivity screening, proper handling and disposal protocols are essential to mitigate any potential risks. Ongoing research aims to develop greener synthetic routes that reduce waste and hazardous byproducts.

The future prospects for 3,5-dichloro-2-methoxyphenol are bright, with continued interest from both academic and industrial researchers. As drug discovery efforts evolve toward more targeted therapies and sustainable practices, compounds like this will remain pivotal in advancing scientific knowledge and developing innovative solutions.

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