Diisobutylaluminium hydride
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IUPAC name
Diisobutylaluminium hydride
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Other names
DIBAH; DIBAL; DiBAlH; DIBAL-H; DIBALH
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Identifiers | |
3D model (
JSmol ) |
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ChemSpider | |
ECHA InfoCard
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100.013.391 |
EC Number |
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PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C8H19Al (monomer) C16H38Al2 (dimer) | |
Molar mass | 142.22 g/mol (monomer) 284.44 g/mol (dimer) |
Appearance | Colorless liquid |
Density | 0.798 g/cm3 |
Melting point | −80 °C (−112 °F; 193 K) |
Boiling point | 116 to 118 °C (241 to 244 °F; 389 to 391 K) at 1 mmHg |
Reacts with water | |
Solubility | Soluble in hydrocarbons, THF, and ether |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
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ignites in air |
GHS labelling: | |
Danger | |
H220, H225, H250, H260, H314 | |
P210, P222, P223, P231+P232, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P302+P334, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P335+P334, P363, P370+P378, P377, P381, P402+P404, P403, P403+P235, P405, P422, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Diisobutylaluminium hydride (DIBALH, DIBAL, DIBAL-H or DIBAH) is a
Properties
Like most organoaluminum compounds, the compound's structure is most probably more than that suggested by its
DIBAL can be prepared by heating
- (i-Bu3Al)2 → (i-Bu2AlH)2 + 2 (CH3)2C=CH2
Although DIBAL can be purchased commercially as a colorless liquid, it is more commonly purchased and dispensed as a solution in an organic solvent such as toluene or hexane.
Use in organic synthesis
DIBAL is useful in
Although DIBAL reliably reduces nitriles to aldehydes, the reduction of esters to aldehydes is infamous for often producing large quantities of alcohols. Nevertheless, it is possible to avoid these unwanted byproducts through careful control of the reaction conditions using continuous flow chemistry.[4]
DIBALH was investigated originally as a
Safety
DIBAL, like most alkylaluminium compounds, reacts violently with air and water, potentially leading to explosion.[6]
References
- ^ ISBN 0471936235.
- .
- ISBN 0-12-234950-4.
- PMID 22206502.
- .
- ^ Thermo Fisher Scientific, Regulatory Affairs (January 3, 2005). "Safety Data Sheet Diisobutylaluminum hydride". Thermo Fisher Scientific. Retrieved October 9, 2023.
External links
- Stockman, R. (2001). "Dibal reduction of an amino acid derived methyl ester; Garner's Aldehyde". ChemSpider Synthetic Pages. doi:10.1039/SP161. SyntheticPage 161.[permanent dead link]
- "Oxidation And Reduction Reactions in Organic Chemistry". University of Southern Maine, Department of Chemistry. Archived from the original on 2011-06-11.
- "Diisobutyl Aluminum hydride (DIBAL-H) and Other Isobutyl Aluminum Alkyls (DIBAL-BOT, TIBAL) as Specialty Organic Synthesis Reagents" (PDF). Akzo-Nobel. Archived from the original (PDF) on 2011-04-08. Retrieved 2011-02-23.