256870
Diisobutylaluminum hydride solution
1.0 M in toluene
Synonym(s):
DIBAL, DIBAL-H
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About This Item
Linear Formula:
[(CH3)2CHCH2]2AlH
CAS Number:
Molecular Weight:
142.22
PubChem Substance ID:
UNSPSC Code:
12352001
Beilstein/REAXYS Number:
4123663
MDL number:
SMILES string
CC(C)C[AlH]CC(C)C
InChI
1S/2C4H9.Al.H/c2*1-4(2)3;;/h2*4H,1H2,2-3H3;;
InChI key
AZWXAPCAJCYGIA-UHFFFAOYSA-N
reaction suitability
reagent type: reductant
concentration
1.0 M in toluene
density
0.858 g/mL at 25 °C
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Application
Used in Pd-catalyzed reductive debromination of secondary alkyl bromides. O-Debenzylation and ring opening of perbenzylated furanosides. Convenient in situ generation of HZrCp2Cl from ZrCp2Cl2 and DIBAL-H.
Other Notes
Angled septum-inlet adapter Z118206 or straight septum-inlet adapter, 6mm I.D. inlet, Z118141 or straight septum-inlet adapter, 13mm I.D. inlet, Z118192 is recommended.
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J Marco-Contelles et al.
Carbohydrate research, 335(1), 63-70 (2001-09-13)
The reaction of DIBALH with bis(heteroannulated)-pyranosides containing the perhydrofuro[2,3-b]pyran moiety is described. The hydride attack at the anomeric carbon (C-9a) resulted in the exclusive tetrahydrofuran ring opening. The selectivity of this reaction has been evaluated as other benzylidene acetals built
Y Kitade et al.
Nucleic acids symposium series, (27)(27), 107-108 (1992-01-01)
Reaction of purine nucleosides, such as 2',3'-isopropylideneinosine (1a) and 2',3'-isopropylideneadenosine (1c), with diisobutylaluminum hydride (DIBAL) in dry tetrahydrofurane resulted in the formation of the corresponding 9-(2',3'-isopropylideneribity)purines (2) in good yields. Oxidation of the ribityl derivatives (2) with NalO4 and subsequent
Hidetsura Cho et al.
The Journal of organic chemistry, 75(3), 627-636 (2009-12-31)
A systematic investigation of the reductive ring-expansion reaction of cyclic ketoximes fused to aromatic rings with diisobutylaluminum hydride (DIBALH) is described. This reaction regioselectively afforded a variety of five- to eight-membered bicyclic heterocycles or tricyclic heterocycles containing nitrogen neighboring an
D J Kopecky et al.
The Journal of organic chemistry, 65(1), 191-198 (2000-05-18)
An optimized protocol for the DIBALH reductive acetylation of acyclic esters and diesters is described. This reductive acetylation procedure allows a wide variety of esters to be converted into the corresponding alpha-acetoxy ethers in good to excellent yields. It was
Damien Webb et al.
Organic letters, 14(2), 568-571 (2011-12-31)
A continuous flow system for the multiparameter (flow rate, temperature, residence time, stoichiometry) optimization of the DIBALH reduction of esters to aldehydes is described. Incorporating an in-line quench (MeOH), these transformations are generally complete in fewer than 60 s. Mixing
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