Iodobenzene, with the CAS number 591-50-4, is an organic compound. Its molecular formula is C₆H₅I, and the molecular weight is approximately 204.01 g/mol. It appears as a colorless to slightly yellow liquid with a characteristic odor. Iodobenzene is insoluble in water but soluble in many organic solvents such as ethanol, ether, and benzene. It has a boiling point of around 188 - 189 °C and a melting point of -31 °C. The refractive index of iodobenzene is about 1.6200.
1. Organic Synthesis: Iodobenzene serves as a crucial starting material in a wide range of organic synthesis reactions. It is often used in the preparation of various aryl compounds through reactions like the Suzuki - Miyaura coupling, Sonogashira coupling, and Heck reaction. These coupling reactions are important for forming carbon - carbon bonds and are widely applied in the synthesis of pharmaceuticals, agrochemicals, and advanced materials.
2. Pharmaceutical Industry: It is used in the synthesis of certain drugs. The iodine atom in iodobenzene can be replaced or transformed to introduce specific functional groups, which is beneficial for the design and synthesis of new drug molecules with desired biological activities.
3. Material Science: In the field of material science, iodobenzene can be used in the synthesis of polymers and organic semiconductors. The unique properties of the aryl - iodine bond allow for the controlled modification of polymer structures, which can improve the electrical, optical, and mechanical properties of materials.
When using iodobenzene, it should be handled in a well - ventilated area or under a fume hood due to its volatility and potential health hazards. Wear appropriate personal protective equipment, including gloves, safety glasses, and a lab coat.
1. Storage: Store iodobenzene in a cool, dry place away from heat sources and direct sunlight. Keep the container tightly closed when not in use to prevent evaporation and contamination.
2. Transfer: When transferring iodobenzene, use suitable glassware and pipettes. Avoid spillage. In case of a spill, immediately clean it up using appropriate absorbent materials and follow proper waste disposal procedures.
3. Reaction Conditions: In organic synthesis reactions, the reaction conditions need to be carefully controlled. For example, in coupling reactions, specific catalysts, bases, and solvents are required. The reaction temperature and reaction time also need to be optimized according to the specific reaction requirements.
1. Pharmaceutical Synthesis: A research group was working on the synthesis of a new anti - cancer drug. They used iodobenzene as a key building block in the Suzuki - Miyaura coupling reaction. By coupling iodobenzene with a boronic acid derivative under the catalysis of a palladium - based catalyst and in the presence of a base, they successfully synthesized an intermediate compound. This intermediate was further modified and transformed to obtain the target anti - cancer drug. The use of iodobenzene in this reaction was crucial for introducing the aryl group into the molecule, which was essential for the drug's biological activity.
2. Polymer Synthesis: In a project related to the development of organic light - emitting diodes (OLEDs), researchers used iodobenzene in the synthesis of a conjugated polymer. They carried out a polymerization reaction using iodobenzene and a diyne monomer through a Sonogashira coupling reaction. The resulting polymer had good solubility and excellent optical properties. When used as the emissive layer in OLEDs, it exhibited high - efficiency light emission, demonstrating the potential of iodobenzene in the field of material science.
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