Alumiiniumdiisobutüülhüdriid

Alumiiniumdiisobutüülhüdriid, also known as diisobutylaluminum hydride (DIBAL-H) or simply DIBAL, is an organoaluminum compound with the chemical formula [(CH3)2CHCH2]2AlH. It is a colorless liquid at room temperature and is commonly used as a reducing agent in organic synthesis. DIBAL-H is a powerful and versatile reagent, capable of reducing a wide range of functional groups, including esters, nitriles, aldehydes, and ketones, to alcohols or aldehydes depending on the reaction conditions and stoichiometry.

The preparation of DIBAL-H typically involves the reaction of triisobutylaluminum with hydrogen gas under pressure. Its reactivity stems from the polar aluminum-hydrogen bond, where the aluminum atom acts as a Lewis acid and the hydride ion acts as a nucleophile. It is often employed at low temperatures to control its reactivity and prevent over-reduction. Solvents commonly used with DIBAL-H include toluene, hexane, and tetrahydrofuran.

In industrial applications, DIBAL-H is utilized in the production of various chemicals, including polymers, pharmaceuticals, and fine chemicals. Its ability to perform selective reductions makes it a valuable tool for chemists aiming to synthesize complex molecules. Care must be taken when handling DIBAL-H due to its pyrophoric nature, meaning it can ignite spontaneously in air, and its reactivity with moisture. It is typically supplied as a solution in an inert solvent.