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214973

Diisobutylaluminum hydride solution

Name: Diisobutylaluminum hydride solution
Brand: ALDRICH

1.0 M in methylene chloride

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

NACRES:

NA.22

PubChem Substance ID:

24852858

eCl@ss:

38120609

UNSPSC Code:

12352001

MDL number:

MFCD00008928

Beilstein/REAXYS Number:

4123663

Form:

liquid

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Properties

form

liquid

Quality Level

200

reaction suitability

reagent type: reductant

concentration

1.0 M in methylene chloride

density

1.23 g/mL at 25 °C

storage temp.

2-8°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

General description

Diisobutylaluminum hydride is a reducing agent for many functional groups commonly used in organic synthesis.

Application

Diisobutylaluminum hydride solution (1 M in dichloromethane) has been used in the conversion of esters into α-fluoro-α,β-unsaturated esters in the presence of fluorocarboalkoxy-substituted dialkyl phosphonate anions via Horner-Wadsworth-Emmons reaction. It can be used in the multi-step synthesis of (S)-2-methyl tetrahydropyridine-N-oxide, a key structural moiety of bio-active compounds like himbacine and solenopsin-A.

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.