2-Chloro-3,4-difluorobenzoic acid
[CAS# 150444-93-2]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Carboxylic acid
• Name: 2-Chloro-3,4-difluorobenzoic acid
• Molecular Formula: C₇H₃ClF₂O₂
• Molecular Weight: 192.55
• CAS Registry Number: 150444-93-2
• SMILES: C1=CC(=C(C(=C1C(=O)O)Cl)F)F

Properties

• Density: 1.6±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.535, Calc.^*
• Boiling Point: 277.9±35.0 °C (760 mmHg), Calc.^*
• Flash Point: 121.9±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-P305+P351+P338

Discovery and Applications

2-Chloro-3,4-difluorobenzoic acid is an organic compound with a molecular structure consisting of a benzoic acid core substituted with chlorine and fluorine atoms at specific positions. It has gained significant attention in various fields of chemistry, particularly in the synthesis of pharmaceuticals, agrochemicals, and other functional materials. Its discovery and development have provided valuable insights into the design of molecules with specific chemical properties.

The compound was first synthesized in the laboratory during the late 20th century as part of a broader effort to create fluorine-containing benzoic acid derivatives. These derivatives were of interest due to their unique properties, which include increased chemical stability and altered solubility characteristics due to the electron-withdrawing effects of the fluorine and chlorine atoms. This made 2-chloro-3,4-difluorobenzoic acid an attractive candidate for a range of applications in both industrial and scientific contexts.

One of the key areas where 2-chloro-3,4-difluorobenzoic acid has found application is in the field of pharmaceutical chemistry. It serves as an intermediate in the synthesis of various bioactive molecules, particularly those with anti-inflammatory, antiviral, or anticancer properties. The presence of fluorine atoms in the molecule enhances the compound's metabolic stability and alters its interaction with biological targets, which is a crucial feature in drug design. Moreover, its functional groups allow for easy incorporation into larger molecular structures, making it a versatile building block for the synthesis of complex pharmaceuticals.

In addition to its use in pharmaceutical applications, 2-chloro-3,4-difluorobenzoic acid has been explored in the development of agrochemicals. It can act as a key component in the synthesis of herbicides and pesticides. The halogen atoms in the molecule contribute to its bioactivity and can enhance its ability to interact with biological systems, making it effective in controlling unwanted plant growth or pests. As the need for more selective and environmentally friendly agrochemicals grows, the role of compounds like 2-chloro-3,4-difluorobenzoic acid is expected to increase, given their potential for fine-tuning activity while minimizing environmental impact.

Moreover, 2-chloro-3,4-difluorobenzoic acid also has applications in material science, particularly in the design of functional materials such as liquid crystals, polymers, and coatings. The unique combination of halogens attached to the aromatic ring imparts specific electronic and steric properties that can be leveraged to develop materials with desired mechanical and thermal properties.

In research settings, 2-chloro-3,4-difluorobenzoic acid continues to be of interest for the exploration of new chemical reactions and synthetic methodologies. Its versatile reactivity allows chemists to modify the compound further to yield a variety of derivatives with specific characteristics, expanding its utility in both academic and industrial research.

Despite its varied applications, 2-chloro-3,4-difluorobenzoic acid must be handled with care, as both chlorine and fluorine are reactive elements. Proper safety precautions are essential when working with this compound, especially in the laboratory setting.

In conclusion, 2-chloro-3,4-difluorobenzoic acid is a valuable chemical compound with important applications in the fields of pharmaceuticals, agrochemicals, and materials science. Its discovery has contributed to the development of more efficient and targeted chemical processes, and its versatility continues to inspire research and innovation across a range of scientific disciplines.

References

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