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Merck

192724

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
UNSPSC Code:
12352001
NACRES:
NA.22
PubChem Substance ID:
24851561
MDL number:
MFCD00008928
Beilstein/REAXYS Number:
4123663

Key Documents

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Product Name

Diisobutylaluminum hydride solution, 25 wt. % in toluene

InChI

1S/2C4H9.Al.H/c2*1-4(2)3;;/h2*4H,1H2,2-3H3;;

SMILES string

CC(C)C[AlH]CC(C)C

InChI key

AZWXAPCAJCYGIA-UHFFFAOYSA-N

form

liquid

reaction suitability

reagent type: reductant

concentration

25 wt. % in toluene

density

0.846 g/mL at 25 °C

Quality Level

200

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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.

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.

Packaging

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

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
SHBS9133
SHBS2946
SHBS2190
STBL0932
STBK5956

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Preparation of arylpropiolate esters from trichlorocyclopropenium cation and elaboration of the esters to unsymmetrical 1, 4-pentadiyn-3-ones and unsymmetrical tellurapyranones
Wadsworth, et al.
The Journal of Organic Chemistry, 52, 3662-3668 (1987)
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)
Takashi Tomioka et al.
The Journal of organic chemistry, 76(11), 4669-4674 (2011-04-30)
Stepwise, selective DIBAL reduction of the acetonide diester derived from tartaric acid followed by the Horner-Emmons reaction effectively provided desymmetrized hydroxy mono-olefination products in a one-pot operation.
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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