1-Chloro-2-[(4-ethoxyphenyl)methyl]-4-iodobenzene
[CAS# 1103738-29-9]

Identification

• Classification: Organic raw materials >> Ether compounds and their derivatives >> Ether, ether alcohol
• Name: 1-Chloro-2-[(4-ethoxyphenyl)methyl]-4-iodobenzene
• Molecular Formula: C₁₅H₁₄ClIO
• Molecular Weight: 372.63
• CAS Registry Number: 1103738-29-9
• EC Number: 822-455-1
• SMILES: CCOC1=CC=C(C=C1)CC2=C(C=CC(=C2)I)Cl

Properties

• Solubility: Insoluble (1.6E^-3 g/L) (25 °C), Calc.^*
• Density: 1.531±0.06 g/cm³ (20 °C 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2013 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Discovery and Applications

1-Chloro-2-[(4-ethoxyphenyl)methyl]-4-iodobenzene is an organic compound that has gained recognition for its potential in various applications, particularly in the fields of medicinal chemistry and materials science. The compound features a benzene ring substituted with chlorine, iodine, and a 4-ethoxyphenylmethyl group, making it a valuable intermediate for the synthesis of more complex molecules. The discovery of this compound has paved the way for innovative applications in drug development and advanced materials.

The discovery of 1-Chloro-2-[(4-ethoxyphenyl)methyl]-4-iodobenzene was driven by the need to develop versatile intermediates that could be used in cross-coupling reactions, a fundamental process in organic synthesis. The presence of both chlorine and iodine atoms on the benzene ring provides unique reactivity, allowing the compound to participate in various coupling reactions, such as Suzuki-Miyaura and Stille couplings. These reactions are essential for forming carbon-carbon bonds, which are crucial in constructing complex organic molecules used in pharmaceuticals and other high-value chemicals.

One of the primary applications of 1-Chloro-2-[(4-ethoxyphenyl)methyl]-4-iodobenzene is in the synthesis of biologically active compounds. The compound's structure serves as a versatile platform for the introduction of different functional groups, enabling the creation of molecules with potential therapeutic effects. For instance, the ethoxyphenyl group can enhance the compound's lipophilicity, which is often desirable in drug design for improving the bioavailability of pharmaceuticals. Additionally, the iodine atom provides a handle for further functionalization, allowing chemists to explore a wide range of chemical space in the search for new drugs.

In medicinal chemistry, 1-Chloro-2-[(4-ethoxyphenyl)methyl]-4-iodobenzene has been used as a precursor in the development of kinase inhibitors, a class of drugs that target enzymes involved in cell signaling pathways. These inhibitors are crucial in treating various cancers and other diseases characterized by abnormal cell growth. The compound's structural features allow for the selective targeting of specific kinases, leading to the development of more effective and safer drugs.

Beyond its role in drug development, 1-Chloro-2-[(4-ethoxyphenyl)methyl]-4-iodobenzene has applications in materials science. Its ability to undergo further chemical modifications makes it a valuable building block for the synthesis of polymers and other advanced materials with tailored properties. For example, by incorporating this compound into polymer chains, researchers can design materials with specific electronic or optical characteristics, which are useful in electronic devices, sensors, and other high-tech applications.

The versatility of 1-Chloro-2-[(4-ethoxyphenyl)methyl]-4-iodobenzene as a synthetic intermediate highlights its importance in both medicinal chemistry and materials science. Its discovery has provided researchers with a powerful tool for developing new drugs and advanced materials, contributing to significant advancements in these fields. As research continues, this compound is expected to play an increasingly important role in the development of innovative solutions to complex scientific challenges.

References

2019. Design, synthesis and anticancer activities of halogenated Phenstatin analogs as microtubule destabilizing agent. Medicinal Chemistry Research.
DOI: 10.1007/s00044-019-02299-4

2017. Glycosyl Stille Cross-Coupling with Anomeric Nucleophiles - A General Solution to a Long-Standing Problem of Stereocontrolled Synthesis of C-Glycosides. Synlett.
DOI: 10.1055/s-0036-1589020