Tetranbutylammoniumiodid

Tetranbutylammoniumiodid, often abbreviated as TBA I, is a quaternary ammonium salt with the chemical formula (CH3CH2CH2CH2)4NI. It is a white crystalline solid that is soluble in many organic solvents and water. This compound is widely used in organic synthesis as a phase-transfer catalyst and as a source of iodide ions. Its bulky tetrabutylammonium cation helps to solubilize the iodide anion in organic phases, facilitating reactions that would otherwise be slow or impossible. TBA I can also be used as a nucleophilic iodide source in substitution reactions. It is a common reagent in halide exchange reactions, such as the Finkelstein reaction, and in the synthesis of alkyl iodides from alkyl halides or tosylates. The thermal stability of tetrabutylammoniumiodid is moderate, and it can decompose at elevated temperatures. Care should be taken during handling and storage to avoid moisture, as it is hygroscopic. Its applications extend to areas such as polymer synthesis and electrochemistry. The compound is typically synthesized by reacting tetrabutylammonium hydroxide with hydroiodic acid or by reacting tetrabutylammonium bromide with sodium iodide.