(3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydro-furan
[CAS# 915095-94-2]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: (3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydro-furan
• Molecular Formula: C₁₇H₁₆ClIO₂
• Molecular Weight: 414.66
• CAS Registry Number: 915095-94-2
• EC Number: 619-599-0
• SMILES: C1COC[C@H]1OC2=CC=C(C=C2)CC3=C(C=CC(=C3)I)Cl

Properties

• Solubility: Insoluble (1.7E^-3 g/L) (25 °C), Calc.^*
• Density: 1.578±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Boiling point: 476.0±45.0 °C (760 mmHg)

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

Safety Data

• Hazard Symbols: GHS09 Warning
• Risk Statements: H400-H410
• Safety Statements: P273-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410

Discovery and Applications

The chemical substance (3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydro-furan is a complex organic molecule known for its distinctive structure and functional properties. This compound consists of a tetrahydrofuran ring connected to a phenoxy group, which is further substituted with a phenyl group containing both chlorine and iodine atoms. The specific (3S) configuration at the tetrahydrofuran ring is essential for the molecule's properties and potential applications.

The synthesis of (3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydro-furan involves multiple chemical steps. The construction of the tetrahydrofuran ring typically requires cyclization reactions from suitable precursors. The phenoxy and substituted phenyl groups are introduced through halogenation and coupling reactions. Achieving the correct stereochemistry at the (3S) position requires precise control during synthesis, ensuring that the molecule exhibits its intended properties.

This compound's applications span several fields, including medicinal chemistry, materials science, and agrochemicals. In medicinal chemistry, (3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydro-furan is valued for its potential as a pharmacological agent. The halogen substituents on the phenyl ring can influence the molecule's interaction with biological targets, potentially enhancing its efficacy and selectivity. Researchers are exploring its use in developing new drugs with improved therapeutic profiles.

In materials science, the unique structure of (3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydro-furan makes it a candidate for designing advanced materials. The tetrahydrofuran ring and substituted phenyl groups can be utilized to create polymers or composites with specific properties, such as enhanced mechanical strength or electronic characteristics. These materials have potential applications in electronics, sensors, and other high-tech industries.

Additionally, (3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydro-furan may find uses in agrochemicals. The compound's structure allows for the development of novel pesticides or herbicides. By leveraging the phenyl and tetrahydrofuran groups, researchers can design agrochemical agents that are more effective against specific pests or plant diseases, contributing to improved crop protection and yield.

The discovery and application of (3S)-3-[4-[(2-Chloro-5-iodophenyl)methyl]phenoxy]tetrahydro-furan demonstrate its importance in advancing chemical research and technology. Its versatile applications in medicinal chemistry, materials science, and agrochemicals highlight its potential to contribute significantly to these fields.

References

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DOI: 10.1007/s00044-019-02299-4

2017. Empagliflozin. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-05-0133

2014. Synthesis of SGLT-2 Inhibitor Empagliflozin. Synfacts, 10(11).
DOI: 10.1055/s-0034-1379221