214981
Diisobutylaluminum hydride solution
1.0 M in THF
Synonym(s):
DIBAL, DIBAL-H
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About This Item
Linear Formula:
[(CH3)2CHCH2]2AlH
CAS Number:
Molecular Weight:
142.22
NACRES:
NA.22
PubChem Substance ID:
eCl@ss:
38120609
UNSPSC Code:
12352001
MDL number:
Beilstein/REAXYS Number:
4123663
Form:
liquid
form
liquid
Quality Level
reaction suitability
reagent type: reductant
concentration
1.0 M in THF
bp
65 °C
density
0.866 g/mL at 25 °C
storage temp.
2-8°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 solution (1M in THF) is a powerful reducing agent. It can be used in the following reactions:
- Synthesis of trans-alkene isosteres of protected dipeptides.
- To generate bis(1,5-cyclooctadiene)nickel(0) (Ni(cod)2) in situ, which can catalyze the conjugate addition of ethenyltributyltin to 2-propenal to form tert-butyldimethyl[((E)-1,4pentadienyl)oxy]silane.
- Reduction of the arylpropiolate esters to give the corresponding propargyl alcohol.
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
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signalword
Danger
target_organs
Central nervous system, Respiratory system
supp_hazards
Storage Class
4.2 - Pyrophoric and self-heating hazardous materials
wgk
WGK 1
flash_point_f
1.4 °F - closed cup
flash_point_c
-17 °C - closed cup
ppe
Faceshields, Gloves, Goggles
Hazard Classifications
Acute Tox. 4 Oral - Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Pyr. Liq. 1 - Skin Corr. 1B - STOT SE 3 - Water-react. 1
Regulatory Information
危险化学品
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A stereocontrolled synthesis of trans-alkene isosteres of dipeptides.
Spaltenstein A, et al.
Tetrahedron Letters, 27(19), 2095-2098 (1986)
Hidetsura Cho et al.
The Journal of organic chemistry, 75(3), 627-636 (2009-12-31)
A systematic investigation of the reductive ring-expansion reaction of cyclic ketoximes fused to aromatic rings with diisobutylaluminum hydride (DIBALH) is described. This reaction regioselectively afforded a variety of five- to eight-membered bicyclic heterocycles or tricyclic heterocycles containing nitrogen neighboring an
D J Kopecky et al.
The Journal of organic chemistry, 65(1), 191-198 (2000-05-18)
An optimized protocol for the DIBALH reductive acetylation of acyclic esters and diesters is described. This reductive acetylation procedure allows a wide variety of esters to be converted into the corresponding alpha-acetoxy ethers in good to excellent yields. It was
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 214981-100ML | 04061838773289 |
| 214981-18L-C | 04061838230997 |
| 214981-18L-KL | 04061838134998 |
| 214981-4X25ML | 04065268447376 |
| 214981-800ML | 04061838773296 |
| 214981-PZ | 04061823819763 |