6-Methoxy-2-(4-methoxyphenyl)benzo[b]thiophene: A Comprehensive Overview of Its Chemical Properties and Applications

 6-Methoxy-2-(4-methoxyphenyl)benzo[b]thiophene is a compound that belongs to the class of organic molecules known as benzothiophenes, which are sulfur-containing heterocycles. The compound's structure is characterized by a benzene ring fused to a thiophene ring, a five-membered ring containing a sulfur atom. Additionally, it has methoxy groups attached to the benzene and thiophene rings, which influence its physical and chemical properties.

A dark, moody laboratory with beakers and test tubes, illuminated by a soft blue light, with the compound's chemical structure displayed on a computer screen

The presence of methoxy groups on the benzene and thiophene rings can alter the compound's electronic configuration and reactivity. These groups can contribute to the electron-donating nature of the compound, affecting how it interacts with other substances. As a result, 6-Methoxy-2-(4-methoxyphenyl)benzo[b]thiophene is of interest in various fields of research, including material science, pharmacology, and organic synthesis.

Researchers are particularly interested in the synthesis of this compound due to its potential applications. It can serve as a building block for more complex molecules or as an intermediate in the synthesis of pharmaceutically relevant compounds. The study of such molecules underscores the importance of understanding the intrinsic properties of benzothiophenes and their derivatives in the design of new materials and drugs.

Chemical Properties

The chemical properties of 6-Methoxy-2-(4-methoxyphenyl)benzo[b]thiophene include its molecular structure, physical characteristics, and its solubility and stability under various conditions.

Molecular Structure

6-Methoxy-2-(4-methoxyphenyl)benzo[b]thiophene consists of a benzo[b]thiophene core substituted with methoxy groups at positions 6 and 2'. The molecule's conjugated system and sulfur heteroatom have notable effects on its electronic properties.

  • Molecular Formula: C_15H_12O_2S

  • Molecular Weight: 256.32 g/mol

Physical Characteristics

This compound is characterized by its solid state at room temperature and its distinct melting point. It displays a color range from white to off-white powder.

  • Melting Point: Between 155 - 160°C

  • Boiling Point: Not readily available due to decomposition

  • Appearance: White to off-white solid

Solubility and Stability

6-Methoxy-2-(4-methoxyphenyl)benzo[b]thiophene shows varying solubility across different solvents and demonstrates specific stability characteristics:

  • Solubility:

    • In Water: Insoluble

    • In Organic Solvents (DMSO, Chloroform): Soluble to moderately soluble

  • Stability: Stable under normal laboratory conditions. It may be sensitive to prolonged exposure to light and moisture.

Applications and Usages

6-Methoxy-2-(4-methoxyphenyl)benzo[b]thiophene exhibits properties significant to medical therapeutics and scientific research.

Medical Relevance

This compound is a synthetic intermediate that has been utilized in the development of various pharmaceutical drugs. Specifically, it is a key precursor in synthesizing modulators of the estrogen receptor, which are important in the treatment of hormone-related cancers. Listed below are drugs where the compound serves a crucial role:

  • Raloxifene: Used to prevent osteoporosis in postmenopausal women.

  • Arzoxifene: An investigational drug for conditions like breast cancer.

The compound's relevance in medicine extends further to its role in creating selective estrogen receptor modulators (SERMs), highlighting its versatility in addressing multiple estrogen-related disorders.

Research Significance

In the realm of research, 6-Methoxy-2-(4-methoxyphenyl)benzo[b]thiophene is of great significance due to its influence on analyzing estrogenic activity. Researchers employ it to study:

  • Binding affinity to estrogen receptors

  • Molecular behavior in cancer cell lines

  • Potential modifications to enhance therapeutic efficacy

Data garnered from such studies assist in understanding the structure-activity relationships (SAR) which can lead to the discovery of new drugs. The compound's role is pivotal in advancing knowledge on treating diseases with an estrogenic factor.
Location: India

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