13Diiodobenzene

1,3-Diiodobenzene is an organic compound with the chemical formula C6H4I2. It is a derivative of benzene where two iodine atoms are substituted at the meta positions of the benzene ring. It exists as a solid at room temperature. The synthesis of 1,3-diiodobenzene can be achieved through various methods, often involving the iodination of benzene or related precursors. One common approach is the Sandmeyer reaction, where an aniline derivative is diazotized and then treated with potassium iodide. Alternatively, direct iodination of benzene under specific conditions can yield diiodinated products, with separation required to isolate the meta isomer. 1,3-Diiodobenzene is sparingly soluble in water but soluble in common organic solvents. Its reactivity is primarily associated with the carbon-iodine bonds, which can participate in various organic transformations. These include cross-coupling reactions, such as Suzuki or Sonogashira couplings, where the iodine atoms serve as leaving groups to form new carbon-carbon bonds. It can also undergo nucleophilic aromatic substitution under forcing conditions, although this is less common than reactions involving transition metal catalysis. Applications of 1,3-diiodobenzene are mainly found in academic research as a building block for more complex molecules. Its ability to undergo diverse coupling reactions makes it useful in the synthesis of functionalized aromatic systems, polymers, and materials science applications where precise control over molecular architecture is desired. Due to the presence of heavy iodine atoms, it may also find niche applications in areas requiring radiopaque properties, though this is not a primary use.