Bis(3-fluorophenyl) sulfide
[CAS# 21099-60-5]

Identification

• Name: Bis(3-fluorophenyl) sulfide
• Synonyms: 1-fluoro-3-[(3-fluorophenyl)sulfanyl]benzene
• Molecular Formula: C₁₂H₈F₂S
• Molecular Weight: 222.25
• CAS Registry Number: 21099-60-5
• SMILES: c1cc(cc(c1)Sc2cccc(c2)F)F

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.602, Calc.^*
• Boiling Point: 307.8±27.0 ºC (760 mmHg), Calc.^*
• Flash Point: 140.0±23.7 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Discovory and Applicatios

The discovery of bis(3-fluorophenyl) sulfide dates back to the mid-20th century, when researchers sought to explore the properties of fluorinated aromatic compounds. It was found that the introduction of fluorine atoms into aromatic rings significantly altered the electronic properties and stability of the resulting molecules. In bis(3-fluorophenyl) sulfide, the sulfur atom acts as a bridge between two 3-fluorophenyl groups, resulting in compounds with unique physical and chemical properties.

The synthesis of bis(3-fluorophenyl) sulfide involves the reaction of 3-fluorothiophenol with electrophiles or through coupling reactions between 3-fluoroiodobenzene and thiophenol. This synthetic route emphasizes the accessibility of the compound and the influence of the fluorine atom on its reactivity.

Bis(3-fluorophenyl) sulfide occurs as a crystalline solid characterized by its chemical stability and ability to participate in a wide range of chemical transformations. The fluorine atom at the 3-position of the benzene ring introduces an electron-withdrawing effect that enhances the reactivity of the compound in synthetic applications.

Bis(3-fluorophenyl) sulfide is a key intermediate in organic synthesis. Its sulfur bridge provides a means for further functionalization, enabling the creation of complex molecular structures. This utility is essential for the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals.

The compound is valuable in cross-coupling reactions such as Suzuki-Miyaura coupling and Buchwald-Hartwig coupling. These reactions allow the formation of carbon-carbon and carbon-nitrogen bonds, which are essential for the construction of a variety of organic molecules. The presence of fluorine atoms enhances the reactivity and selectivity of these coupling processes, facilitating the efficient synthesis of complex structures.

Bis(3-fluorophenyl)sulfide serves as a building block for the manufacture of a variety of fluorinated compounds. Additional functional groups can be introduced through various transformations, making it a versatile precursor for the development of molecules with tailored electronic and steric properties.

In materials science, bis(3-fluorophenyl)sulfide is used to develop organic electronic materials. Its aromatic structure combined with the electron-withdrawing effect of fluorine atoms enhances charge transport properties, making it suitable for organic light-emitting diodes (OLEDs) and organic field-effect transistors (OFETs), helping to advance flexible electronics and display technologies.

The compound is also used in the synthesis of conductive polymers. These polymers exhibit unique electronic properties and have applications in sensors, transistors, and photovoltaic cells. The presence of fluorine atoms improves the thermal stability and electrical conductivity of these polymers, enhancing their performance in electronic devices.

Bis(3-fluorophenyl) sulfide can serve as a scaffold for drug discovery. Its structure allows for the introduction of a variety of substituents, resulting in derivatives with potential therapeutic properties. The compound and its derivatives are studied as anticancer agents. The fluorine atoms and sulfur bonds help the compounds interact with biological targets and inhibit cancer cell growth. Research focuses on optimizing these derivatives to increase their activity against cancer cells while minimizing toxicity.

Bis(3-fluorophenyl) sulfide derivatives also show promise as antiviral agents. The structure of the compound can be modified to target specific viral proteins, providing a potential treatment for viral infections. The fluorine atoms enhance the ability of the compounds to penetrate biological membranes and improve their stability in physiological environments.