3,4-Difluoronitrobenzene

3,4-Difluoronitrobenzene (CAS: 369-34-6) is an important organic intermediate widely utilized in pharmaceutical, agrochemical, and material science applications. Its molecular formula is C₆H₃F₂NO₂, with a molecular weight of 159.09 g/mol.

Physical Properties

The compound appears as a colorless to light yellow transparent liquid. It has a melting point of -12°C, a boiling point of 76-80°C at 11 mmHg, and a density of 1.437 g/mL at 25°C. The calculated LogP value is approximately 2.1, indicating moderate lipophilicity, and the topological polar surface area is 45.8 Ų.

Structural Features

The molecule consists of a benzene ring with two fluorine atoms at the 1- and 2-positions (ortho to each other) and a nitro group at the 4-position. The systematic IUPAC name is 1,2-difluoro-4-nitrobenzene. This specific substitution pattern creates unique electronic properties, with the electron-withdrawing fluorine and nitro groups activating the ring toward nucleophilic aromatic substitution reactions.

Key Applications

Pharmaceutical Development: The compound serves as a crucial intermediate in the synthesis of various pharmaceuticals, including xanthones and acridones, which possess potential biological activities and fluorescence properties.

Agricultural Chemistry: It is used as an intermediate for pesticides and herbicides, contributing to crop protection products.

Material Science: The compound is employed in developing advanced materials, including polymers and coatings, due to its unique electronic properties and stability.

Organic Synthesis: Researchers leverage its reactivity to create complex molecules via nucleophilic aromatic substitution reactions.

Safety and Handling

The compound is classified as an irritant (GHS07). Hazard statements include H315 (causes skin irritation), H319 (causes serious eye irritation), and H335 (may cause respiratory irritation). It should be stored in a cool, dry, well-ventilated area away from oxidizing agents. Standard laboratory protective equipment including gloves and safety goggles should be used during handling.

Commercial Availability

3,4-Difluoronitrobenzene is commercially available at ≥98-99% purity from major suppliers such as Sigma-Aldrich, Chem-Impex, and Alfa Chemistry. Typical packaging sizes range from 10g to 50g for research use, with larger quantities available for industrial applications.

In summary, 3,4-Difluoronitrobenzene is a versatile and valuable building block for synthetic chemists, enabling efficient access to diverse chemical libraries in drug discovery, crop protection, and advanced materials development. Its well-defined physical properties and predictable reactivity make it an essential tool in both academic and industrial research settings.