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Safety Information

190306

Sigma-Aldrich

Diisobutylaluminum hydride solution

1.0 M in hexanes

Synonym(s):

DIBAL, DIBAL-H

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About This Item

Linear Formula:
[(CH3)2CHCH2]2AlH
CAS Number:
Molecular Weight:
142.22
Beilstein:
4123663
MDL number:
UNSPSC Code:
12352001
PubChem Substance ID:
NACRES:
NA.22

form

liquid

Quality Level

reaction suitability

reagent type: reductant

concentration

1.0 M in hexanes

density

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

Application

Diisobutylaluminum hydride solution (1.0 M in hexanes) can be used in the synthesis of potassium diisobutyl-t-butoxyaluminum hydride (PDBBA), a novel reducing agent for the chemoselective conversion of esters in the presence of nitriles. The DIBAL-triethylamine complex can reduce α-oxoketene dithioacetal to the saturated ketone.
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.

Signal Word

Danger

Hazard Classifications

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

Target Organs

Central nervous system, Nervous system

Supplementary Hazards

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 3

Flash Point(F)

-9.4 °F - closed cup

Flash Point(C)

-23 °C - closed cup


Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Class I Designated Chemical Substances

FSL

Group 3: Spontaneously combustible substances and water- reactive materials
Materials containing Alkyl aluminum
Hazardous rank II
2nd spontaneously combustible materials and water reactive materials

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

190306-8L:4548173250243
190306-20L:
190306-18L:4548173112220
190306-4X100ML:4548173907307
190306-2L:
190306-800ML:4548173112237
190306-PZ:
190306-VAR:
190306-100ML:4548173112213
190306-BULK:


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alpha.-Oxoketene dithioacetal chemistry. 2. Conjugate reductions with electrophilic reducing agents.
Gammill R
The Journal of Organic Chemistry, 46(17), 3555-3558 (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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