(2-Chloro-5-iodophenyl)(4-fluorophenyl)methanone
[CAS# 915095-86-2]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: (2-Chloro-5-iodophenyl)(4-fluorophenyl)methanone
• Molecular Formula: C₁₃H₇ClFIO
• Molecular Weight: 360.55
• CAS Registry Number: 915095-86-2
• EC Number: 619-596-4
• SMILES: C1=CC(=CC=C1C(=O)C2=C(C=CC(=C2)I)Cl)F

Properties

• Density: 1.752
• Boiling point: 415 °C
• Flash point: 205 °C

Safety Data

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

Hazard Classification

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

Discovery and Applications

(2-Chloro-5-iodophenyl)(4-fluorophenyl)methanone is an important chemical compound featuring a methanone group bonded to two distinct aromatic rings. Each ring has different halogen substituents: one ring contains chlorine and iodine, while the other ring is fluorinated. This specific arrangement of halogen atoms imparts unique chemical and physical properties to the molecule, which are exploited in various applications.

The discovery of (2-Chloro-5-iodophenyl)(4-fluorophenyl)methanone stems from research aimed at developing new halogenated aromatic ketones. Halogenation of aromatic rings is a common strategy in organic synthesis to modify the reactivity, stability, and solubility of molecules. The introduction of chlorine, iodine, and fluorine atoms into the structure enhances its utility in several chemical domains due to the distinct electronic and steric effects of these halogens.

Synthesis of (2-Chloro-5-iodophenyl)(4-fluorophenyl)methanone typically involves the Friedel-Crafts acylation reaction, which is used to introduce the methanone group to the aromatic rings. This process requires precise control over reaction conditions and the use of specific catalysts to ensure the formation of the desired product. The halogenation of the phenyl rings can be achieved through standard halogenation techniques, which involve treating the starting materials with halogenating agents under controlled conditions.

In the pharmaceutical industry, (2-Chloro-5-iodophenyl)(4-fluorophenyl)methanone serves as a crucial intermediate in the synthesis of various bioactive compounds. The presence of multiple halogen atoms in the structure can significantly affect the biological activity of the resultant molecules. For example, the introduction of fluorine and iodine can alter the lipophilicity and metabolic stability of drug candidates, making them more effective or selective for their intended targets. The compound’s halogenated nature also plays a role in modulating the pharmacokinetics and pharmacodynamics of pharmaceuticals.

In materials science, the unique properties of (2-Chloro-5-iodophenyl)(4-fluorophenyl)methanone make it a valuable building block for the development of advanced materials. The halogenated aromatic ketone can be used to synthesize new polymers, organic light-emitting diodes (OLEDs), and other functional materials. The combination of different halogens in the molecule provides a way to fine-tune the electronic and optical properties of the materials, leading to improved performance in electronic devices and other applications.

In addition to its use in pharmaceuticals and materials science, (2-Chloro-5-iodophenyl)(4-fluorophenyl)methanone is utilized in agrochemicals and specialty chemicals. The compound’s ability to undergo further chemical modifications makes it suitable for the synthesis of novel agrochemical agents with enhanced efficacy and selectivity. Its halogenated structure also contributes to the development of specialty chemicals with specific properties tailored to various industrial needs.

Overall, (2-Chloro-5-iodophenyl)(4-fluorophenyl)methanone is a versatile compound with significant implications in synthetic chemistry, pharmaceuticals, and materials science. Its discovery and application highlight the importance of halogenated aromatic ketones in advancing chemical research and developing new technologies.

References

2019. Design, synthesis and anticancer activities of halogenated Phenstatin analogs as microtubule destabilizing agent. Medicinal Chemistry Research, 28(4).
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