3,4-Difluoroaniline

3,4-Difluoroaniline (CAS: 3863-11-4) is an important organic intermediate widely utilized in pharmaceutical, agrochemical, and material science applications. Its molecular formula is C₆H₅F₂N, with a molecular weight of 129.11 g/mol. The compound features a benzene ring substituted with two fluorine atoms at the 3- and 4-positions and an amino group (-NH₂) at the 1-position, creating an electron-deficient aromatic system.

Physical Properties

The compound appears as a clear colorless to pale yellow liquid at room temperature, with a melting point of 22°C and a boiling point of 77°C at 7 mmHg. It has a density of 1.302 g/mL at 25°C and a refractive index of n20/D 1.513. The calculated LogP value is approximately 1.48, indicating moderate lipophilicity, and the topological polar surface area is 26.02 Ų.

Key Applications

• Pharmaceutical Development: 3,4-Difluoroaniline serves as a crucial building block in drug synthesis, particularly for developing kinase inhibitors and antitumor agents. It has been used to prepare thiourea-containing sorafenib analogs and fluorinated benzothiazoles as potential anticancer compounds.

• Agrochemical Formulation: The compound is widely utilized in producing herbicides and fungicides, enhancing crop protection and yield.

• Material Science: It is explored for developing advanced polymers and coatings with enhanced chemical resistance. The compound is also used in synthesizing azomethine ligands for zinc(II) complexes studied for blue-emitting OLED applications.

Synthesis and Handling

The compound is typically synthesized by catalytic hydrogenation of 3,4-difluoronitrobenzene with over 93% yield. It should be stored in a dark place under an inert atmosphere at room temperature, protected from moisture and oxidizing agents.

Specifications

Commercial grades are available at 98-99% purity from suppliers such as AK Scientific, Aladdin, and Sigma-Aldrich. Typical packaging sizes range from 5g to 1kg for research and industrial applications.

In summary, 3,4-Difluoroaniline is a versatile and valuable intermediate for synthetic chemists, enabling efficient access to diverse chemical libraries in drug discovery, crop protection, and advanced materials development.