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Sigma-Aldrich

Diisobutylaluminum hydride solution

25 wt. % in toluene

Synonym(s):

DIBAL, DIBAL-H

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About This Item

Linear Formula:
[(CH3)2CHCH2]2AlH
CAS Number:
1191-15-7
Molecular Weight:
142.22
Beilstein/REAXYS Number:
4123663
MDL number:
MFCD00008928
UNSPSC Code:
12352001
PubChem Substance ID:
24851561
NACRES:
NA.22

form

liquid

Quality Level

200

reaction suitability

reagent type: reductant

concentration

25 wt. % in toluene

density

0.846 g/mL at 25 °C

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

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General description

Diisobutylaluminum hydride solution is a strong reducing agent used to convert arylpropiolate esters to their propargyl alcohols.

Diisobutylaluminum hydride reducing agent is commonly used for the reduction of an ester to aldehyde.

Application

Diisobutylaluminum hydride solution (25 wt. % in toluene) has been used for the reduction of imides:
  • N

  • -(cis-2-Vinylcyclohexyl)succinimide to 1-(cis-2-vinylcyclohexyl)-5-hydroxy-2-pyrrolidinone
  • N-(But-4-en-1-y1)-2(E)-(carbethoxymethylidene)-5-oxo-pyrrolidine to N-(but-4-en-1-yl)- 2(E)-(carbethoxymethylidene)-5-hydroxypyrrolidine
  • N-(Hept-1-en-4-y1)-2(E)-(carbethoxymethylidene)-5-oxo-pyrrolidine to N-(hept-1-en-4-y1)-2(E)-(carbethoxymethylidene)-5-hydroxypyrrolidine
  • N-(cis-2-Vinylcyclohexyl)-2-(carbethoxymethylidene)-5-oxopyrrolidine to rel-(3aR,SS,5aS,SaR)-1( E)-(carbethoxymethylidene)-5-(formyloxy)dodecahydropyrrolo[1,2-a]quinoline

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.

Packaging

The 25 g Sure/Seal™ bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.
View returnable container options.

Legal Information

Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

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Danger

Hazard Classifications

Aquatic Chronic 3 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Pyr. Liq. 1 - Repr. 2 - Skin Corr. 1B - STOT RE 2 Inhalation - STOT SE 3 - Water-react 1

target_organs

Central nervous system

supp_hazards

EUH014

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

wgk_germany

WGK 3

flash_point_f

39.2 °F - closed cup

flash_point_c

4 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
STBK5956
STBK4293
STBK2818
SHBN0408
STBJ7750

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Vinylogous N-acyliminium ion cyclizations: application to the synthesis of depentylperhydrogephyrotoxin.
Hart DJ
The Journal of Organic Chemistry, 46(2), 367-373 (1981)
Chemoselective Reduction of Esters to Aldehydes by Potassium Diisobutyl-t-butoxyaluminum Hydride (PDBBA).
Chae MJ, et al.
Bull. Korean Chem. Soc., 28(12), 2517-2517 (2007)
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
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
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