Diisobutylaluminium hydride

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Diisobutylaluminium hydride
Names
IUPAC name
Diisobutylaluminium hydride
Other names
DIBAH; DIBAL; DiBAlH; DIBAL-H; DIBALH
Identifiers
3D model (
JSmol
)
ChemSpider
ECHA InfoCard
100.013.391 Edit this at Wikidata
EC Number
  • 214-729-9
UNII
  • InChI=1S/2C4H9.Al.H/c2*1-4(2)3;;/h2*4H,1H2,2-3H3;; checkY
    Key: AZWXAPCAJCYGIA-UHFFFAOYSA-N checkY
  • InChI=1/2C4H9.Al.H/c2*1-4(2)3;;/h2*4H,1H2,2-3H3;;/rC8H19Al/c1-7(2)5-9-6-8(3)4/h7-9H,5-6H2,1-4H3
    Key: AZWXAPCAJCYGIA-DFAADSFOAF
  • CC(C)C[AlH]CC(C)C
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
ignites in air
GHS labelling:
GHS02: FlammableGHS05: Corrosive
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).
checkY verify (what is checkY☒N ?)

Diisobutylaluminium hydride (DIBALH, DIBAL, DIBAL-H or DIBAH) is a

organoaluminium compound is a reagent in organic synthesis.[1]

Properties

Like most organoaluminum compounds, the compound's structure is most probably more than that suggested by its

alkyl
groups.

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

nucleophilic
reducing agent.

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

cocatalyst for the polymerization of alkenes.[5]

Safety

DIBAL, like most alkylaluminium compounds, reacts violently with air and water, potentially leading to explosion.[6]

References

  1. ^ .
  2. .
  3. .
  4. .
  5. .
  6. ^ Thermo Fisher Scientific, Regulatory Affairs (January 3, 2005). "Safety Data Sheet Diisobutylaluminum hydride". Thermo Fisher Scientific. Retrieved October 9, 2023.

External links