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215007

Sigma-Aldrich

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:
1191-15-7
Molecular Weight:
142.22
Beilstein:
4123663
MDL number:
MFCD00008928
UNSPSC Code:
12352001
eCl@ss:
38120609
PubChem Substance ID:
24852861
NACRES:
NA.22

form

liquid

Quality Level

200

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

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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.
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Legal Information

Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

Signal Word

Danger

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

Target Organs

Central nervous system

Supplementary Hazards

EUH014

Storage Class Code

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Class I Designated Chemical Substances

FSL

Group 3: Spontaneously combustible substances and water- reactive materials
Materials containing Alkyl aluminum
Hazardous rank II
2nd spontaneously combustible materials and water reactive materials

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

215007-800ML:4548173116679
215007-4X100ML:
215007-PZ:
215007-VAR:
215007-8L:4548173116686
215007-18L:4548173116662
215007-100ML:4548173116655
215007-BULK:
215007-18L-C:
215007-20L:
215007-4X25ML:4548173309101
215007-4X10ML:
215007-18L-KL:

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR6962
SHBS0559
SHBS0567
SHBR5665
STBK5190

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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
J Marco-Contelles et al.
Carbohydrate research, 335(1), 63-70 (2001-09-13)
The reaction of DIBALH with bis(heteroannulated)-pyranosides containing the perhydrofuro[2,3-b]pyran moiety is described. The hydride attack at the anomeric carbon (C-9a) resulted in the exclusive tetrahydrofuran ring opening. The selectivity of this reaction has been evaluated as other benzylidene acetals built
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
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