Benzyl iodide

Benzyl iodide, also known as iodomethylbenzene, is a chemical compound with the formula C₆H₅CH₂I. It is a colorless liquid, although it can appear yellowish due to impurities. Benzyl iodide is used primarily in organic synthesis, serving as a source of the benzyl group in various chemical reactions.

Properties

Benzyl iodide has a molecular weight of 218.01 g/mol and boils at 200-202 °C. It is less dense than water, with a density of 1.808 g/cm³. Being an alkyl halide, it is reactive, especially in the presence of base, and is considered a good alkylating agent.

Synthesis

Benzyl iodide can be synthesized through several methods. One common approach involves the reaction of benzyl chloride with sodium iodide in acetone, which substitutes the chlorine atom with an iodine atom. Another method is the direct iodination of toluene with iodine in the presence of oxidizing agents like nitric acid.

Applications

In organic chemistry, benzyl iodide is used as a reagent to introduce the benzyl group into other molecules. Its applications include:

• Synthesis of benzyl esters and ethers by reaction with alcohols and phenols.
• Preparation of benzyl-protected amines and alcohols, which are important intermediates in the synthesis of pharmaceuticals and fine chemicals.
• Use in phase-transfer catalysis as an alkylating agent.

Safety

Benzyl iodide is a hazardous material. It is corrosive to skin and eyes and can cause severe burns. Inhalation or ingestion of benzyl iodide can lead to iodide poisoning, which manifests as skin lesions, pulmonary edema, and kidney damage. Proper safety equipment, such as gloves and goggles, should be used when handling this chemical.

See Also

• Alkyl halide
• Organic synthesis
• Benzyl group
• Phase-transfer catalysis