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:
Molecular Weight:
142.22
UNSPSC Code:
12352001
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
4123663
form
liquid
Quality Level
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.
Diisobutylaluminum hydride reducing agent is commonly used for the reduction of an ester to aldehyde.
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.
Packaging
The 25 g Sure/Seal™ bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.
Legal Information
Sure/Seal is a trademark of Sigma-Aldrich Co. LLC
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Danger
target_organs
Central nervous system
supp_hazards
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
Regulatory Information
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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)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 192724-15KG | 04061838760623 |
| 192724-100G | 04061838125330 |
| 192724-700G | 04061838760630 |
| 192724-PZ | 04061823819220 |
| 192724-4X25G | 04061833301401 |
| 192724-7KG | 04061838118455 |