7,8-Difluoro-dibenzo[b,e]thiepin-11(6H)-one
[CAS# 2136287-66-4]

Identification

• Classification: Organic raw materials >> Ketone compound
• Name: 7,8-Difluoro-dibenzo[b,e]thiepin-11(6H)-one
• Molecular Formula: C₁₄H₈F₂OS
• Molecular Weight: 262.27
• CAS Registry Number: 2136287-66-4
• SMILES: C1C2=C(C=CC(=C2F)F)C(=O)C3=CC=CC=C3S1

Properties

• Solubility: Insoluble (1.3E^-3 g/L) (25 °C), Calc.^*
• Density: 1.393±0.06 g/cm³ (20 °C 760 Torr), Calc.^* (Expl.)
• Index of Refraction: 1.627, Calc.^*
• Boiling Point: 427.7±45.0 °C (760 mmHg), Calc.^*
• Flash Point: 212.5±28.7 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2018 ACD/Labs)

Safety Data

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

Discovery and Applications

7,8-Difluoro-dibenzo[b,e]thiepin-11(6H)-one is a chemical compound that belongs to the class of dibenzo[b,e]thiepin derivatives, which are heterocyclic compounds containing both sulfur and aromatic rings. This particular compound features two fluorine atoms at the 7 and 8 positions on the benzene ring, as well as a ketone functional group at the 11 position. The structure of 7,8-difluoro-dibenzo[b,e]thiepin-11(6H)-one contributes to its distinct chemical properties and makes it of interest for various scientific studies.

The discovery of 7,8-difluoro-dibenzo[b,e]thiepin-11(6H)-one is part of ongoing research into the synthesis and applications of dibenzo[b,e]thiepin derivatives. These compounds have drawn attention due to their diverse biological activities, which include neurochemical effects and potential therapeutic applications. The introduction of fluorine atoms into the structure of organic compounds can alter their reactivity, stability, and biological activity, making fluorinated derivatives particularly valuable in medicinal chemistry. In the case of 7,8-difluoro-dibenzo[b,e]thiepin-11(6H)-one, the addition of fluorine atoms enhances its potential as a drug candidate.

The synthesis of 7,8-difluoro-dibenzo[b,e]thiepin-11(6H)-one typically involves several steps, including the construction of the dibenzothiepin core and the introduction of fluorine atoms at specific positions. One common approach involves the fluorination of a dibenzothiepin intermediate, followed by the introduction of the ketone functional group at the 11 position. These reactions require careful control of reaction conditions to ensure high yields and the desired regioselectivity of fluorination. Techniques such as chromatography and crystallization are often used to purify the product after synthesis.

One of the key applications of 7,8-difluoro-dibenzo[b,e]thiepin-11(6H)-one is in the field of medicinal chemistry, particularly as a lead compound for the development of drugs targeting neurological disorders. The parent dibenzo[b,e]thiepin structure is known for its potential as an antidepressant, antipsychotic, and neuroprotective agent, and fluorination can enhance the pharmacological properties of the compound. Research into its biological activity has indicated that derivatives of dibenzo[b,e]thiepin, such as 7,8-difluoro-dibenzo[b,e]thiepin-11(6H)-one, may be effective in modulating neurotransmitter systems involved in mood disorders, schizophrenia, and neurodegenerative diseases.

In addition to its potential therapeutic applications, 7,8-difluoro-dibenzo[b,e]thiepin-11(6H)-one is of interest in the development of materials and organic electronics. The fluorination of aromatic compounds can modify their electronic properties, making them suitable for use in organic semiconductors and other electronic devices. The compound may also be studied for its interaction with light and its use in organic light-emitting diodes (OLEDs) or other optoelectronic applications.

In conclusion, 7,8-difluoro-dibenzo[b,e]thiepin-11(6H)-one is a promising compound with applications in medicinal chemistry and materials science. Its unique structure, featuring fluorine substitution and a ketone group, makes it an interesting candidate for drug development, particularly for neurological disorders. Ongoing research into its synthesis, biological activity, and electronic properties continues to reveal its potential across multiple fields.

References

2020. Synthesis of a Baloxavir Marboxil Fragment. *Synfacts*, 16(03).
DOI: 10.1055/s-0039-1691695