Iodobenzene (CAS 591-50-4) is a fundamental organic compound with a rich history of synthesis and a diverse array of properties that underpin its widespread use. NINGBO INNO PHARMCHEM CO.,LTD. provides insights into the preparation and characteristics that define this essential chemical.

The traditional and most common method for synthesizing Iodobenzene involves the diazotization of aniline followed by a Sandmeyer-type reaction with potassium iodide. In this process, aniline is first treated with sodium nitrite in the presence of an acid (like hydrochloric acid) at low temperatures to form a diazonium salt. This intermediate is then reacted with potassium iodide, leading to the substitution of the diazonium group with an iodine atom, yielding Iodobenzene. This method is generally efficient, with yields often around 77%, and is a standard laboratory procedure.

Physically, Iodobenzene is characterized as a colorless to pale yellow liquid with a distinct odor. Its molecular formula is C6H5I, and it has a molecular weight of 204.01 g/mol. Key physical properties include a melting point of approximately -29 °C and a boiling point of around 188 °C. It is largely insoluble in water but readily soluble in organic solvents such as ethanol, ether, and chloroform. A notable characteristic is its photosensitivity; it tends to turn yellow upon prolonged exposure to light, necessitating storage in amber bottles or in a cool, dark place.

Chemically, the strength of the carbon-iodine bond is weaker than its carbon-bromine or carbon-chlorine counterparts. This makes Iodobenzene more reactive in nucleophilic substitution reactions and in organometallic chemistry. As previously mentioned, its facile reaction with magnesium to form phenylmagnesium iodide is a testament to this enhanced reactivity, making it a preferred precursor for Grignard reagents. Furthermore, its participation in palladium-catalyzed cross-coupling reactions, such as the Suzuki, Heck, and Sonogashira reactions, highlights its importance in modern synthetic organic chemistry.

For professionals looking to buy Iodobenzene, understanding these synthetic routes and inherent properties is crucial for selecting the right grade and ensuring optimal results in their applications. Whether for intricate organic synthesis or precise analytical calibration, the preparation and properties of Iodobenzene are key to its value.