To use all functions of this page, please activate cookies in your browser.
With an accout for my.chemeurope.com you can always see everything at a glance – and you can configure your own website and individual newsletter.
- My watch list
- My saved searches
- My saved topics
- My newsletter
Diisobutylaluminium hydride, DIBAL, DIBAL-H or DIBAH, is a reducing agent with the formula (i-Bu2AlH)2, where i-Bu represents isobutyl (-CH2CH(CH3)2). This organoaluminium compound was investigated originally as a co-catalyst for the polymerization of alkenes.
Additional recommended knowledge
Like most organoaluminum compounds, the compound’s structure is more than that suggested by its empirical formula. It is dimeric, consisting of a pair of tetrahedral aluminium centers sharing bridging hydride ligands. Hydrides are small and, for aluminium derivatives, are highly basic, thus they bridge in preference to the alkyl groups.
Although DIBAH can be purchased commercially as a colorless liquid, it is more commonly purchased and dispensed as a solution in organic solvents such as toluene.
Use in organic synthesis
DIBAH is useful in organic synthesis for a variety of reductions, including converting esters and nitriles to aldehydes. By contrast, LiAlH4 reduces esters and acyl chlorides to primary alcohols, and NaBH4 fails to reduce most esters. DIBAH reacts slowly with electron poor compounds, and more quickly with electron rich compounds. Thus, it is an electrophilic reducing agent whereas LiAlH4 can be thought of as a nucleophilic reducing agent.
DIBAH, like most alkylaluminium compounds, reacts violently with air and water, potentially leading to fires.
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Diisobutylaluminium_hydride". A list of authors is available in Wikipedia.|