215007
Diisobutylaluminum hydride solution
1.0 M 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
NACRES:
NA.22
PubChem Substance ID:
eCl@ss:
38120609
UNSPSC Code:
12352001
MDL number:
Beilstein/REAXYS Number:
4123663
form
liquid
Quality Level
reaction suitability
reagent type: reductant
concentration
1.0 M in toluene
density
0.858 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 solution (1M in toluene) has been used for the reduction of aziridine esters to the corresponding aldehydes. It has also been used in the synthesis of dialkylaluminum alkoxides from alcohols.
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 mL 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
flash_point_f
39.2 °F - closed cup
flash_point_c
4 °C - closed cup
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
易制毒化学品（3类）
危险化学品
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Synthesis of peptide macrocycles using unprotected amino aldehydes.
Rotstein BH, et al.
Nature Protocols, 5(11), 1813-1813 (2010)
Macromolecular engineering of polyactones and polyactides. 12. Study of the depolymerization reactions of poly (. epsilon.-caprolactone) with functional aluminum alkoxide end groups.
Dubois P, et al.
Macromolecules, 26(17), 4407-4412 (1993)
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
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 215007-18L-KL | 04061838231017 |
| 215007-4X100ML | 04061838125651 |
| 215007-PZ | 04061826597262 |
| 215007-18L-C | 04061838125644 |
| 215007-100ML | 04061838773319 |
| 215007-4X25ML | 04061838773326 |
| 215007-800ML | 04061838773333 |