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Diisobutyl aluminum hydride, also known as DIBAL-H, is a chemical compound with the formula (CH3)2CHCH2CH2AlH2. It is an organoaluminum compound and is commonly used as a reducing agent in organic synthesis.
DIBAL-H is a powerful reducing agent that can selectively reduce a variety of functional groups, including esters, amides, nitriles, and ketones, to their corresponding alcohols. It is particularly useful for reducing esters to aldehydes, which can be further reduced to primary alcohols.
DIBAL-H is a pyrophoric compound, meaning it reacts violently with air and moisture. Therefore, it must be handled with extreme caution and under an inert atmosphere, such as nitrogen or argon. It is typically supplied as a solution in anhydrous hydrocarbon solvents, such as hexanes or toluene, to prevent contact with air and moisture.
In addition to its reducing properties, DIBAL-H can also act as a Lewis acid, meaning it can coordinate with electron-rich compounds to form complexes. This property makes it useful in various synthetic reactions, such as the formation of carbon-carbon bonds or the activation of certain functional groups.
Overall, diisobutyl aluminum hydride is a versatile and powerful reagent in organic synthesis, widely used for selective reductions and other synthetic transformations.
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