Bis(3,5-difluorophenyl)sulfoxide
[CAS# 2055858-27-8]

Identification

• Name: Bis(3,5-difluorophenyl)sulfoxide
• Synonyms: 1-(3,5-difluorophenyl)sulfinyl-3,5-difluorobenzene
• Molecular Formula: C₁₂H₆F₄OS
• Molecular Weight: 274.23
• CAS Registry Number: 2055858-27-8
• SMILES: C1=C(C=C(C=C1F)S(=O)C2=CC(=CC(=C2)F)F)F

Properties

• Density: 1.5±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.592, Calc.^*
• Boiling Point: 360.6±42.0 ºC (760 mmHg), Calc.^*
• Flash Point: 171.9±27.9 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335-H402-H412
• Precautionary Statements: P261-P264-P270-P271-P273-P280-P301+P312+P330-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501

Discovory and Applicatios

Bis(3,5-difluorophenyl)sulfoxide, also known as DFPSO, is a unique organosulfur compound. The discovery of bis(3,5-difluorophenyl)sulfoxide dates back to the mid-20th century, when efforts were devoted to exploring the unique chemical reactivity and potential uses of sulfoxides in various fields. Sulfoxides are characterized by a sulfur atom double-bonded to oxygen, as well as single-bonded to two carbon-containing groups. In DFPSO, these carbon-containing groups are 3,5-difluorophenyl rings, i.e., aromatic rings substituted with fluorine atoms at the 3- and 5-positions. The introduction of fluorine atoms enhances the electronic properties of the molecule, making it an important intermediate in organic synthesis and a valuable compound for creating materials with desirable properties.

DFPSO is synthesized by oxidation of bis(3,5-difluorophenyl)sulfide, usually using an oxidizing agent such as hydrogen peroxide or m-chloroperbenzoic acid (m-CPBA). This oxidation introduces the sulfoxide functional group, resulting in a compound with remarkable chemical stability and unique reactivity.

DFPSO is a versatile intermediate in organic synthesis. Its sulfoxide group provides handling for a variety of transformations, including reduction to sulfides or oxidation to sulfones. This versatility makes DFPSO a useful building block for the synthesis of complex molecules in pharmaceuticals and agrochemicals.

In asymmetric synthesis, DFPSO derivatives can be used as chiral auxiliaries. The sulfur center can coordinate with metal catalysts, helping to create a chiral environment that enables the selective synthesis of enantiomerically pure compounds. This application is critical for the development of drugs with specific biological activities and minimizing side effects.

DFPSO derivatives are explored for use as ligands in catalysis, especially in metal-catalyzed reactions. The sulfoxide group can coordinate with transition metals, enhancing the catalytic activity and selectivity of the reaction. This property is valuable for the development of efficient catalytic systems for a variety of organic transformations, including hydrogenations and cross-coupling reactions.

In materials science, DFPSO is used to develop organic electronic materials. Its unique electronic properties, influenced by the fluorine atom, are suitable for the manufacture of semiconductors and light-emitting materials. These materials are essential for the development of organic light-emitting diodes (OLEDs) and other flexible electronic devices, helping to advance display technology and wearable electronics.

DFPSO is incorporated into the synthesis of fluorinated polymers. These polymers exhibit exceptional thermal stability, chemical resistance, and good mechanical properties for use in coatings, membranes, and high-performance materials. The fluorine atoms enhance the polymer's resistance to degradation and improve its performance in harsh environments.

DFPSO can serve as a scaffold for drug development. It is capable of a variety of chemical modifications that allow the creation of derivatives with potential therapeutic properties. Researchers use DFPSO to design compounds that target different biological pathways, aiming to develop drugs with greater efficacy and selectivity.

DFPSO derivatives act as pharmacophores, the parts of molecules responsible for their biological activity. The fluorine atoms influence the interaction of the compound with the biological target, enhancing binding affinity and stability under physiological conditions. This property makes DFPSO derivatives valuable in the design of drugs to treat cancer, inflammation, and other diseases.

Studies on DFPSO derivatives have explored their potential as antimicrobial agents. The sulfoxide group and fluorine atoms contribute to the compounds' ability to penetrate bacterial cell membranes and inhibit essential enzymes, providing potential treatments for bacterial infections.