2-Fluoro-5-iodobenzonitrile: Properties, Applications, and Synthesis
2-Fluoro-5-iodobenzonitrile, also known as 5-Iodo-2-fluorobenzonitrile, is an organic compound with the molecular formula C7H3FIN. It is widely used in the pharmaceutical industry as a key intermediate in the synthesis of various drugs. This article discusses the properties, applications, and synthesis of 2-Fluoro-5-iodobenzonitrile.
Properties of 2-Fluoro-5-iodobenzonitrile
2-Fluoro-5-iodobenzonitrile is a white to light yellow crystalline powder with a melting point of 124-128°C. It is soluble in organic solvents such as methanol, ethanol, and acetone but insoluble in water. The compound has a molecular weight of 301.01 g/mol and a density of 2.038 g/cm3.
Applications of 2-Fluoro-5-iodobenzonitrile
2-Fluoro-5-iodobenzonitrile is an important intermediate in the synthesis of various drugs, including anti-cancer drugs, anti-inflammatory agents, and antipsychotics.
Anti-cancer drugs: Several anti-cancer drugs such as Fludarabine, Idarubicin, and Doxorubicin use 2-Fluoro-5-iodobenzonitrile as a key intermediate in their synthesis. These drugs are used for the treatment of various types of cancers such as leukemia, lymphoma, breast, and lung cancer.
Anti-inflammatory agents: The compound is also used in the synthesis of several anti-inflammatory agents such as Ibuprofen and Naproxen. These drugs are used for the treatment of pain and inflammation caused by conditions such as arthritis and menstrual cramps.
Antipsychotics: 2-Fluoro-5-iodobenzonitrile is also used in the synthesis of antipsychotic drugs such as Clozapine and Olanzapine. These drugs are used for the treatment of mental illnesses such as schizophrenia and bipolar disorder.
Synthesis of 2-Fluoro-5-iodobenzonitrile
2-Fluoro-5-iodobenzonitrile can be synthesized by various methods, including the following:
Method 1: The synthesis of 2-Fluoro-5-iodobenzonitrile can be achieved by the reaction of 2-Fluorobenzonitrile with iodine in the presence of a base such as potassium hydroxide. The reaction is carried out in an organic solvent such as acetone or DMF.
Method 2: Another method involves the reaction of 2-Fluoro-5-nitrobenzonitrile with potassium iodide and sodium borohydride in the presence of a catalyst such as palladium on carbon. The reaction is carried out in an organic solvent such as ethanol or methanol.
Method 3: 2-Fluoro-5-iodobenzonitrile can also be synthesized by the reaction of 2-Fluoro-5-bromobenzonitrile with sodium iodide in the presence of a catalyst such as copper(I) iodide. The reaction is carried out in an organic solvent such as DMF or DMSO.
Conclusion
2-Fluoro-5-iodobenzonitrile is an important intermediate in the synthesis of various drugs used in the pharmaceutical industry. The compound possesses several important properties such as high solubility in organic solvents and a relatively high density. The synthesis of 2-Fluoro-5-iodobenzonitrile can be achieved by several methods, including the reaction of 2-Fluorobenzonitrile with iodine and the reduction of 2-Fluoro-5-nitrobenzonitrile with potassium iodide and sodium borohydride.
