Benzyl iodide is an organic compound with the chemical formula C7H7I. It consists of a benzyl group (C₆H₅CH₂-) attached to an iodine atom. The compound consists of a benzene ring with an attached iodidemethyl group. The substance is an alkyl halide and is a constitutional isomer of the iodotoluenes. It is a colorless to pale yellow liquid that has a sweet odor.
Properties
Benzyl iodide forms colorless to yellow needles, melting at 24.5 °C. As a liquid, the compound has the high refractive index of 1.6334. Benzyl iodide is also a powerful lachrymator.
- Chemical formula: C7H7I
- Molar mass: 218.037 g·mol−1
- Appearance: Low-melting crystals or colorless liquid
- Melting point: 24.5 °C
- Boiling point: 218 °C (424 °F; 491 K)
- Solubility in water: Insoluble
Preparation:
Benzyl iodide can be synthesized through various methods, such as:
Reaction of benzyl alcohol with iodine: C6H5CH2OH+I2→C6H5CH2I+HI
Reaction of benzyl chloride with sodium iodide (Finkelstein reaction): C6H5CH2Cl+NaI→C6H5CH2I+NaCl
Uses
- Organic Synthesis: Benzyl iodide is often used in organic chemistry as an alkylating agent in reactions such as nucleophilic substitution (SN2).
- Synthesis of Benzyl Derivatives: It is used to prepare other benzyl compounds, such as benzyl ethers, esters, or amines.
- Industrial Applications: It finds application in the manufacture of pharmaceuticals, perfumes, and other chemical products.
Reactivity
- Benzyl iodide undergoes nucleophilic substitution reactions easily due to the leaving group (I⁻). It can react with various nucleophiles such as amines, alcohols, thiols, or even water under certain conditions.
- It is also used in Wurtz-type reactions for the synthesis of higher alkanes.
Safety Considerations
- Irritant: It can cause irritation to the skin, eyes, and respiratory system, so appropriate safety measures should be taken when handling it.
- Toxicity: Inhalation or ingestion of benzyl iodide can be harmful.
