190306
Diisobutylaluminum hydride solution
1.0 M in hexanes
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
form
liquid
Quality Level
reaction suitability
reagent type: reductant
concentration
1.0 M in hexanes
density
0.701 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 reducing agent is commonly used for the reduction of an ester to aldehyde.
Application
Diisobutylaluminum hydride solution (1.0 M in hexanes) can be used in the synthesis of potassium diisobutyl-t-butoxyaluminum hydride (PDBBA), a novel reducing agent for the chemoselective conversion of esters in the presence of nitriles. The DIBAL-triethylamine complex can reduce α-oxoketene dithioacetal to the saturated ketone.
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.
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signalword
Danger
target_organs
Central nervous system, Nervous system
supp_hazards
Storage Class
4.2 - Pyrophoric and self-heating hazardous materials
wgk
WGK 3
flash_point_f
-9.4 °F - closed cup
flash_point_c
-23 °C - closed cup
Hazard Classifications
Aquatic Chronic 2 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Pyr. Liq. 1 - Repr. 2 - Skin Corr. 1B - STOT RE 1 Inhalation - STOT SE 3 - Water-react. 1
Regulatory Information
危险化学品
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alpha.-Oxoketene dithioacetal chemistry. 2. Conjugate reductions with electrophilic reducing agents.
Gammill R
The Journal of Organic Chemistry, 46(17), 3555-3558 (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.
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 190306-PZ | 04061823819169 |
| 190306-800ML | 04061838759764 |
| 190306-100ML | 04061838759757 |
| 190306-4X100ML | 04061838118448 |