Diisobutylaluminium hydride

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Diisobutylaluminium hydride

IUPAC name[hide] Diisobutylaluminum hydride Other names[hide] DIBAH; DIBAL; DiBAlH; DIBAL-H; DIBALH

CAS number ChemSpider Jmol-3D images

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Identifiers 1191-15-7 10430352 Image 1 SMILES

InChI
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Properties C16H38Al2 (dimer) 142.22 (monomer) colorless liquid 0.798 g/cm3 18 C 116118 C/1 mmHg hydrocarbon solvents Hazards Main hazards ignites in air (what is this?) (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 C, 100 kPa) Infobox references Molecular formula Molar mass Appearance Density Melting point Boiling point Solubility in water

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.[1]

Contents
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1 Properties 2 Use in organic synthesis 3 Safety 4 References 5 External links

Properties
Like most organoaluminum compounds, the compounds structure is probably more than that suggested by its empirical formula. A variety of techniques, not including X-ray crystallography, suggest that the compound exists as a dimer and a trimer, consisting of tetrahedral aluminium centers sharing bridging hydride ligands.[2] Hydrides are small and, for aluminium derivatives, are highly basic, thus they bridge in preference to the alkyl groups. DIBAH can be prepared by heating triisobutylaluminium (itself a dimer) to induce betahydride elimination:[3] (i-Bu3Al)2 (i-Bu2AlH)2 + 2 (CH3)2C=CH2 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. DIBAH efficiently reduces - unsaturated esters to the corresponding allylic alcohol.[4] By contrast, LiAlH4 reduces esters and acyl chlorides to primary alcohols, and nitriles to primary amines [use Feiser work-up procedure]. 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.

Safety
DIBAH, like most alkylaluminium compounds, reacts violently with air and water, potentially leading to fires.