214965
Diisobutylaluminum hydride solution
1.0 M in heptane
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
eCl@ss:
38120609
Form:
liquid
form
liquid
Quality Level
reaction suitability
reagent type: reductant
concentration
1.0 M in heptane
density
0.731 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
Application
Diisobutylaluminum hydride (DIBAL-H) is a common reducing agent to reduce aldehydes, ketones, esters, acids and acid chlorides to the corresponding alcohols. Some of the applications are:
- Synthesis of α-acetoxy ethers by reduction and subsequent acetylation of esters.
- Synthesis of coniferyl, sinapyl, and p-coumaryl alcohol by selective reduction of corresponding cinnamate esters.
- Reduction of secondary phosphine oxides (SPOs) to the corresponding phosphines.
- DIBAL-H can also be used in the hydroalumination of alkene and alkynes.
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
supp_hazards
Storage Class
4.2 - Pyrophoric and self-heating hazardous materials
wgk
WGK 2
flash_point_f
30.2 °F
flash_point_c
-1 °C
Hazard Classifications
Aquatic Acute 1 - Aquatic Chronic 1 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Pyr. Liq. 1 - Skin Corr. 1B - STOT SE 3 - Water-react. 1
Regulatory Information
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Applications of diisobutylaluminium hydride (DIBAH) and triisobutylaluminium (TIBA) as reducing agents in organic synthesis.
Winterfeldt E
Synthesis, 1975(09), 617-630 (1975)
General Synthesis of α-Acetoxy Ethers from Esters by DIBALH Reduction and Acetylation.
Dahanukar V H and Rychnovsky S D
The Journal of Organic Chemistry, 61(23), 8317-8320 (1996)
A Superior method for the reduction of secondary phosphine oxides.
Busacca C A, et al.
Organic Letters, 7(19), 4277-4280 (2005)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 214965-800ML | 04061838125637 |
| 214965-100ML | 04061838773258 |