17823-40-4 | 4-BROMO-2,3,5,6-TETRAFLUOROBENZONITRILE

CAS:17823-40-4 | 4-BROMO-2,3,5,6-TETRAFLUOROBENZONITRILE,Description

The compound 4-Bromo-2,3,5,6-tetrafluorobenzonitrile is a halogenated aromatic nitrile with potential applications in various chemical syntheses. It is characterized by the presence of a bromine atom and four fluorine atoms attached to a benzene ring, which also contains a nitrile group. This structure is a derivative of benzonitrile and is modified by the presence of halogen atoms that can influence its reactivity and physical properties.

Synthesis Analysis

The synthesis of derivatives of tetrafluorobenzene, such as 1,4-bis(dimesitylphosphino)-2,3,5,6-tetrafluorobenzene, involves aromatic nucleophilic substitution reactions. For instance, the reaction of lithium dimesitylphosphide with hexafluorobenzene leads to the formation of such compounds. Although the synthesis of 4-Bromo-2,3,5,6-tetrafluorobenzonitrile itself is not detailed in the provided papers, similar synthetic strategies involving halogenated reagents and coupling reactions are mentioned, such as the synthesis of 4′-bromo-2,3,5,6-tetrafluorobiphenyl-4-carbonitrile from 1,4′-bromoiodobenzene and 4-bromo-2,3,5,6-tetrafluorobenzonitrile.

Molecular Structure Analysis

The molecular structure of 4-Bromo-2,3,5,6-tetrafluorobenzonitrile has been determined through X-ray crystallography. The compound crystallizes in the orthorhombic space group P212121, with the two phenyl rings rotated with respect to each other. This rotation and the presence of halogen atoms significantly influence the molecular interactions and packing within the crystal lattice.

Chemical Reactions Analysis

The reactivity of halogenated benzonitriles is influenced by the electron-withdrawing effects of the halogen atoms and the nitrile group. These effects can enhance the electrophilic character of the compound, making it a suitable substrate for nucleophilic aromatic substitution reactions. The presence of a bromine atom also opens up possibilities for further functionalization through palladium-catalyzed cross-coupling reactions, as demonstrated by the synthesis of biphenyl derivatives.

Physical and Chemical Properties Analysis

The physical and chemical properties of 4-Bromo-2,3,5,6-tetrafluorobenzonitrile are influenced by the strong electron-withdrawing effects of the fluorine atoms and the nitrile group. These effects can lead to increased acidity of protons ortho to the nitrile group and may affect the compound's solubility and boiling point. The presence of halogen atoms also contributes to intermolecular interactions such as halogen bonding, which can be observed in the crystal packing of related compounds. The fluorine atoms can engage in C—H⋯F contacts, while the bromine atom can participate in Br⋯F and F⋯F contacts, forming an intermolecular network within the crystal structure.

Scientific Research Applications

• Chemical Synthesis
  • 4-Bromo-2,3,5,6-tetrafluorobenzonitrile is a polyfluoroarene and is used as an aryl fluorinated building block.

• Pharmaceutical Intermediate

  • 4-Bromo-2,3,5,6-tetrafluorobenzonitrile can be used as a pharmaceutical intermediate. This means it can be used in the synthesis of various pharmaceutical drugs. The specific drugs and the methods of synthesis would depend on the drug being synthesized.

• Protein-Protein Interactions Studies

  • 4-Bromo-2,3,5,6-tetrafluorobenzonitrile can be incorporated into probes used to study protein-protein interactions (PPIs), which are crucial for various cellular processes. By attaching the molecule to one protein, researchers can investigate its binding with other proteins, providing insights into potential drug targets and mechanisms of action.

• Quantum Mechanical Calculations

  • Quantum mechanical calculations of energies, geometries and vibrational wave numbers of 4-Bromo-2,3,5,6-tetrafluorobenzonitrile have been performed by DFT level of theory using B3LYP/6-31+G(d) and B3LYP/6-311++G(d,p) as basis sets. The optimized geometrical parameters obtained by B3LYP method show good agreement.

• Preparation of Fluoropyridyl Reagents

  • 4-Bromo-2,3,5,6-tetrafluorobenzonitrile was used in the preparation of 2,3,5,6-tetrafluoro-pyridylcadmium or 2,3,5,6-tetrafluoropyridylzinc reagent.

Safety And Hazards

4-Bromo-2,3,5,6-tetrafluorobenzonitrile is classified as Acute Tox. 4 Dermal, Acute Tox. 4 Inhalation, Acute Tox. 4 Oral, Eye Irrit. 2, Skin Irrit. 2, and STOT SE 3. It is recommended to use personal protective equipment such as a dust mask type N95 (US), eyeshields, and gloves when handling this compound.

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