4-Chloro-3,5-difluorobromobenzene
[CAS# 176673-72-6]

Identification

• Classification: Organic raw materials >> Aryl compounds
• Name: 4-Chloro-3,5-difluorobromobenzene
• Synonyms: 5-Bromo-2-chloro-1,3-difluorobenzene
• Molecular Formula: C₆H₂BrClF₂
• Molecular Weight: 227.43
• CAS Registry Number: 176673-72-6
• EC Number: 800-772-6
• SMILES: C1=C(C=C(C(=C1F)Cl)F)Br

Properties

• Density: 1.8±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.529, Calc.^*
• Boiling Point: 190.5±35.0 °C (760 mmHg), Calc.^*
• Flash Point: 69.0±25.9 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

4-Chloro-3,5-difluorobromobenzene is a halogenated aromatic compound that has gained attention due to its versatility in various chemical reactions and its potential applications in materials science, pharmaceuticals, and organic synthesis. The compound consists of a benzene ring substituted with chlorine, fluorine, and bromine atoms, making it a valuable intermediate for the synthesis of more complex molecules. Its discovery is part of the ongoing exploration of halogenated aromatic compounds, which are known for their unique electronic properties and reactivity.

The synthesis of 4-chloro-3,5-difluorobromobenzene is typically carried out through selective halogenation reactions, where the specific positions of the chlorine, fluorine, and bromine atoms are introduced onto the benzene ring. This method ensures that the compound possesses the desired functional groups, which are crucial for its reactivity in subsequent chemical processes. The presence of both electronegative halogens in different positions on the aromatic ring leads to significant changes in the electronic distribution of the molecule, making it highly reactive and useful in various synthetic pathways.

One of the primary applications of 4-chloro-3,5-difluorobromobenzene is in the field of organic synthesis, where it serves as an intermediate in the preparation of more complex organic compounds. The halogen atoms in the structure provide sites for nucleophilic substitution reactions, enabling the creation of a wide range of derivatives. For instance, this compound can be used to synthesize various biologically active molecules or functional materials, making it valuable in the pharmaceutical industry and materials science.

In the pharmaceutical industry, halogenated aromatic compounds like 4-chloro-3,5-difluorobromobenzene are often employed in the design of new drugs due to their ability to influence the biological activity of the resulting molecules. The strategic placement of halogen atoms can enhance the stability, lipophilicity, and receptor binding properties of drug candidates, making them more effective in therapeutic applications. Research into the development of halogenated pharmaceuticals has led to several important classes of drugs, and compounds like 4-chloro-3,5-difluorobromobenzene are often key intermediates in this process.

In addition to its pharmaceutical applications, 4-chloro-3,5-difluorobromobenzene is also used in materials science. Its halogenated structure makes it an excellent candidate for the preparation of organic semiconductors, which are essential components in the development of organic electronic devices, such as organic light-emitting diodes (OLEDs), organic photovoltaics (OPVs), and organic field-effect transistors (OFETs). The compound's unique electronic properties, stemming from the combination of chlorine, fluorine, and bromine atoms, contribute to its ability to facilitate charge transport and improve the efficiency of these devices.

Furthermore, 4-chloro-3,5-difluorobromobenzene is being explored in the synthesis of new materials with specific optical, electronic, or catalytic properties. Its halogenated nature allows for fine-tuning of its reactivity and functionality, making it a versatile building block in the creation of specialized compounds for various technological and industrial applications.

Overall, the discovery and development of 4-chloro-3,5-difluorobromobenzene highlight the importance of halogenated aromatic compounds in modern chemistry. Its applications in organic synthesis, pharmaceuticals, and materials science demonstrate its potential as a key intermediate in the creation of innovative solutions for a range of industries.

References

2024. Chiral multiple-resonance thermally activated delayed fluorescence materials based on chiral spiro-axis skeleton for efficient circularly polarized electroluminescence. Science China Chemistry.
DOI: 10.1007/s11426-024-2087-1