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214973

Sigma-Aldrich

Diisobutylaluminum hydride solution

1.0 M in methylene chloride

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Synonym(s):
DIBAL, DIBAL-H
Linear Formula:
[(CH3)2CHCH2]2AlH
CAS Number:
Molecular Weight:
142.22
Beilstein/REAXYS Number:
4123663
MDL number:
eCl@ss:
38120609
PubChem Substance ID:
NACRES:
NA.22

form

liquid

Quality Level

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

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This Item
214981192724214949
Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

100

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

storage temp.

-

density

1.23 g/mL at 25 °C

density

0.866 g/mL at 25 °C

density

0.846 g/mL at 25 °C

density

0.781 g/mL at 25 °C

form

liquid

form

liquid

form

liquid

form

liquid

concentration

1.0 M in methylene chloride

concentration

1.0 M in THF

concentration

25 wt. % in toluene

concentration

1.0 M in cyclohexane

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.

signalword

Danger

Hazard Classifications

Carc. 2 - Eye Dam. 1 - Pyr. Liq. 1 - Skin Corr. 1B - STOT SE 3 - Water-react 1

target_organs

Central nervous system

supp_hazards

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

wgk_germany

WGK 2


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Customers Also Viewed

Diisobutylaluminum Hydride.
Galatsis P
e-EROS Encyclopedia of Reagents for Organic Synthesis (2008)
Reduction-olefination of esters: a new and efficient synthesis of. alpha.-fluoro. alpha.,. beta.-unsaturated esters.
Thenappan A
The Journal of Organic Chemistry, 55(15), 4639-4642 (1990)
An enantioselective route to trans-2, 6-disubstituted piperidines
Chackalamannil S
Tetrahedron, 53(32), 11203-11210 (1997)
Reaction of diisobutylaluminum hydride with selected organic compounds containing representative functional groups
Yoon N M
The Journal of Organic Chemistry, 50(14), 2443-2450 (1985)
Carl A Busacca et al.
The Journal of organic chemistry, 73(4), 1524-1531 (2008-01-17)
The reduction of tertiary phosphine oxides (TPOs) and sulfides with diisobutylaluminum hydride (DIBAL-H) has been studied in detail. An extensive solvent screen has revealed that hindered aliphatic ethers, such as MTBE, are optimum for this reaction at ambient temperature. Many

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