Diisobutylaluminum hydride solution

Name: Diisobutylaluminum hydride solution
Brand: ALDRICH

1.0 M in heptane

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

UNSPSC Code:

12352001

NACRES:

NA.22

PubChem Substance ID:

24852857

MDL number:

MFCD00008928

Beilstein/REAXYS Number:

4123663

eCl@ss:

38120609

Form:

liquid

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Properties

form

liquid

Quality Segment

200

reaction suitability

reagent type: reductant

concentration

1.0 M in heptane

density

0.731 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

Description

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.

Diisobutylaluminum hydride (DIBAL-H) is a common reducing agent to reduce aldehydes, ketones, esters, acids and acid chlorides to the corresponding alcohols. Some of the applications are:

Synthesis of α-acetoxy ethers by reduction and subsequent acetylation of esters.
Synthesis of coniferyl, sinapyl, and p-coumaryl alcohol by selective reduction of corresponding cinnamate esters.
Reduction of secondary phosphine oxides (SPOs) to the corresponding phosphines.
DIBAL-H can also be used in the hydroalumination of alkene and alkynes.