Diisobutüülalumiiniumhüdriid

Diisobutüülalumiiniumhüdriid, commonly abbreviated as DIBAL-H, is an organoaluminium compound with the chemical formula ((CH₃)₂CHCH₂)₂AlH. It is a pyrophoric, colorless liquid, though it is often handled as a solution in organic solvents like hexane, toluene, or tetrahydrofuran. DIBAL-H is a strong reducing agent and is widely used in organic synthesis.

Its primary application is the reduction of various functional groups. It can reduce esters to aldehydes at low temperatures or to primary alcohols at higher temperatures. Nitriles are reduced to imines, which can then be hydrolyzed to aldehydes. Carboxylic acids can also be reduced to primary alcohols. DIBAL-H is also employed in the hydroalumination of alkenes and alkynes, leading to the formation of organoaluminium intermediates that can be further functionalized.

The selectivity of DIBAL-H as a reducing agent makes it a valuable tool in complex molecule synthesis. Its ability to stop the reduction at the aldehyde stage is particularly useful for preparing compounds that are sensitive to over-reduction. Due to its reactive nature, DIBAL-H must be handled with care in an inert atmosphere, typically under nitrogen or argon, to prevent contact with air and moisture, which can lead to ignition or decomposition.