(5-Bromo-2-chlorophenyl)(4-fluorophenyl)methanone
[CAS# 915095-85-1]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Ketones
• Name: (5-Bromo-2-chlorophenyl)(4-fluorophenyl)methanone
• Molecular Formula: C₁₃H₇BrClFO
• Molecular Weight: 313.55
• CAS Registry Number: 915095-85-1
• SMILES: C1=CC(=CC=C1C(=O)C2=C(C=CC(=C2)Br)Cl)F

Properties

• Solubility: Insoluble (3.4E^-3 g/L) (25 °C), Calc.^*
• Density: 1.568±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Boiling point: 390.6±37.0 °C (760 mmHg)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2017 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Discovery and Applications

(5-Bromo-2-chlorophenyl)(4-fluorophenyl)methanone, often referred to in the literature by its IUPAC name, is a compound of considerable interest due to its unique combination of halogenated aromatic rings. This molecule features a central ketone group attached to two aromatic rings with distinct substituents: a bromine and a chlorine on one ring and a fluorine on the other. This structural arrangement imparts specific properties to the compound, making it valuable in various chemical and pharmaceutical applications.

The discovery of (5-Bromo-2-chlorophenyl)(4-fluorophenyl)methanone emerged from efforts to explore the chemical properties and applications of halogenated aromatic ketones. The introduction of halogen atoms into the phenyl rings of methanone derivatives often enhances their reactivity and modulates their electronic properties. In this case, the combination of bromine, chlorine, and fluorine atoms offers a platform for investigating the effects of halogen substitution on molecular behavior and reactivity.

The synthesis of (5-Bromo-2-chlorophenyl)(4-fluorophenyl)methanone typically involves the Friedel-Crafts acylation reaction, where a ketone group is introduced to an aromatic ring. The process requires the use of suitable catalysts and reagents to ensure selective and efficient formation of the desired product. The halogenation of the phenyl rings can be achieved through standard halogenation techniques, and the final product is obtained after purification steps to remove any by-products or unreacted materials.

In terms of applications, (5-Bromo-2-chlorophenyl)(4-fluorophenyl)methanone finds utility in several areas. In medicinal chemistry, the compound's halogenated structure is useful in the development of pharmaceutical agents. Halogen substituents often influence the biological activity of compounds, affecting their interactions with biological targets. For instance, fluorine and bromine atoms can impact the lipophilicity and metabolic stability of drugs, making such compounds valuable in designing new pharmaceuticals with optimized properties.

Moreover, (5-Bromo-2-chlorophenyl)(4-fluorophenyl)methanone serves as an intermediate in the synthesis of more complex organic molecules. The presence of the ketone group allows for further chemical modifications, enabling the introduction of additional functional groups. This property is beneficial in the creation of novel compounds with potential applications in various fields, including agrochemicals, materials science, and specialty chemicals.

In materials science, the compound's distinctive halogenated structure contributes to the development of new materials with tailored properties. For example, the incorporation of such molecules into polymer matrices or as building blocks in organic electronic devices can lead to materials with unique electronic or optical characteristics. The ability to fine-tune the electronic properties of the molecule through halogen substitution opens avenues for creating advanced materials with specific functionalities.

Overall, (5-Bromo-2-chlorophenyl)(4-fluorophenyl)methanone represents a valuable compound in both research and industrial applications. Its synthesis and application demonstrate the significance of halogenated aromatic ketones in advancing chemical sciences and developing new technologies.

References

2020. RETRACTED ARTICLE: A NEW HETEROCYCLIC COMPOUND: CRYSTAL STRUCTURE AND ANTICANCER ACTIVITY AGAINST HUMAN LUNG ADENOCARCINOMA CELLS. Journal of Structural Chemistry, 61(7).
DOI: 10.1134/s0022476620070215