Cas no 82477-66-5 (1-Chloro-3-methoxy-5-methylbenzene)

1-Chloro-3-methoxy-5-methylbenzene is a halogenated aromatic compound featuring a chloro substituent at the 1-position, a methoxy group at the 3-position, and a methyl group at the 5-position. This structure imparts unique reactivity, making it a valuable intermediate in organic synthesis, particularly for pharmaceuticals, agrochemicals, and specialty chemicals. The electron-donating methoxy and methyl groups enhance its utility in electrophilic substitution reactions, while the chloro group offers a site for further functionalization. Its stability and well-defined reactivity profile ensure consistent performance in cross-coupling and nucleophilic displacement reactions. The compound is typically supplied with high purity, ensuring reliable results in research and industrial applications.
1-Chloro-3-methoxy-5-methylbenzene structure
82477-66-5 structure
Product Name:1-Chloro-3-methoxy-5-methylbenzene
CAS No:82477-66-5
MF:C8H9ClO
MW:156.609461545944
CID:821004
PubChem ID:12909340
Update Time:2025-10-30

1-Chloro-3-methoxy-5-methylbenzene Chemical and Physical Properties

Names and Identifiers

    • 1-Chloro-3-methoxy-5-methylbenzene
    • 3-Chloro-5-methoxytoluene
    • 3-CHLORO-5-METHYLANISOLE
    • MB05593
    • DTXSID40512713
    • AKOS006284492
    • 82477-66-5
    • SCHEMBL12231
    • FT-0723509
    • CS-0358128
    • MDL: MFCD08234651
    • Inchi: 1S/C8H9ClO/c1-6-3-7(9)5-8(4-6)10-2/h3-5H,1-2H3
    • InChI Key: BQHGEYXFGBISCP-UHFFFAOYSA-N
    • SMILES: ClC1C=C(C=C(C)C=1)OC

Computed Properties

  • Exact Mass: 156.03400
  • Monoisotopic Mass: 156.0341926g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 1
  • Complexity: 105
  • 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: 2.9
  • Topological Polar Surface Area: 9.2?2

Experimental Properties

  • Density: 1.105±0.06 g/cm3 (20 oC 760 Torr),
  • Boiling Point: 100 oC (0.8 Torr)
  • Flash Point: 89.8±15.8 oC,
  • Solubility: Very slightly soluble (0.3 g/l) (25 o C),
  • PSA: 9.23000
  • LogP: 2.65700

1-Chloro-3-methoxy-5-methylbenzene Customs Data

  • HS CODE:2909309090
  • Customs Data:

    China Customs Code:

    2909309090

    Overview:

    2909309090 Other aromatic ethers and their halogenated derivatives\sulfonation\Nitrated derivative(Including nitrosative derivatives).Regulatory conditions:nothing.VAT:17.0%.Tax refund rate:9.0%.MFN tariff:5.5%.general tariff:30.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    2909309090 other aromatic ethers and their halogenated, sulphonated, nitrated or nitrosated derivatives VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0%

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Additional information on 1-Chloro-3-methoxy-5-methylbenzene

Professional Introduction to 1-Chloro-3-methoxy-5-methylbenzene (CAS No. 82477-66-5)

1-Chloro-3-methoxy-5-methylbenzene, identified by its Chemical Abstracts Service (CAS) number 82477-66-5, is a significant organic compound that has garnered attention in the field of pharmaceutical chemistry and material science. This aromatic heterocyclic compound features a benzene ring substituted with a chlorine atom, a methoxy group, and a methyl group at specific positions, which endows it with unique chemical properties and reactivity. Its molecular structure not only makes it a valuable intermediate in synthetic chemistry but also positions it as a potential precursor in the development of novel bioactive molecules.

The structural configuration of 1-Chloro-3-methoxy-5-methylbenzene contributes to its versatility in organic synthesis. The presence of the chloro substituent at the 1-position enhances its electrophilic aromatic substitution potential, allowing for further functionalization through reactions such as nucleophilic aromatic substitution or cross-coupling reactions. Meanwhile, the methoxy and methyl groups introduce electron-donating effects, which can influence the reactivity and electronic properties of the aromatic system. These characteristics make it an attractive candidate for constructing more complex molecular architectures, particularly in medicinal chemistry where precise control over substitution patterns is crucial.

In recent years, there has been growing interest in exploring the pharmacological potential of 1-Chloro-3-methoxy-5-methylbenzene and its derivatives. Researchers have been investigating its role as a building block in the synthesis of various pharmacophores that exhibit antimicrobial, anti-inflammatory, and even anticancer properties. The methoxy group, in particular, has been shown to modulate the bioactivity of related compounds by influencing their solubility and metabolic stability. This has prompted studies into its incorporation into more sophisticated drug candidates designed to target specific disease pathways.

One notable area of research involves the use of 1-Chloro-3-methoxy-5-methylbenzene as a precursor in the synthesis of flavonoid-like compounds. Flavonoids are a class of natural products known for their broad spectrum of biological activities, including antioxidant and anti-inflammatory effects. By leveraging the reactivity of this compound, chemists have been able to develop synthetic routes that mimic natural biosynthesis pathways while introducing novel structural motifs. These efforts have led to the discovery of several derivatives with enhanced pharmacological profiles, demonstrating the compound's utility in drug discovery programs.

The role of 1-Chloro-3-methoxy-5-methylbenzene in material science is equally compelling. Its aromatic nature and functional substituents make it a suitable candidate for designing advanced materials with tailored electronic properties. For instance, researchers have explored its use in the development of organic semiconductors and liquid crystals, where precise control over molecular arrangement and intermolecular interactions is essential. The compound's ability to undergo polymerization or form inclusion complexes with other molecules has opened up new avenues for creating high-performance materials with applications in electronics, optoelectronics, and photonics.

The synthesis of 1-Chloro-3-methoxy-5-methylbenzene typically involves multi-step organic transformations starting from commercially available aromatic precursors. Common synthetic strategies include chlorination reactions followed by selective methylation and demethylation steps to achieve the desired substitution pattern. Advances in catalytic methods have further refined these processes, enabling higher yields and selectivity while reducing environmental impact. Such improvements are critical for large-scale production and ensure that pharmaceutical applications can be met efficiently without compromising sustainability.

In conclusion, 1-Chloro-3-methoxy-5-methylbenzene (CAS No. 82477-66-5) represents a versatile and valuable compound with applications spanning pharmaceuticals and materials science. Its unique structural features facilitate diverse chemical transformations, making it an indispensable tool for synthetic chemists. As research continues to uncover new applications and refine synthetic methodologies, this compound is poised to play an increasingly important role in advancing both academic research and industrial innovation.

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