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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
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form

liquid

Quality Segment

200

reaction suitability

reagent type: reductant

concentration

25 wt. % in toluene

density

0.846 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

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.

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 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

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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signalword

Danger

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

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

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