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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

Certificates of Analysis (COA)

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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)
Synthesis of peptide macrocycles using unprotected amino aldehydes.
Rotstein BH, et al.
Nature Protocols, 5(11), 1813-1813 (2010)
K Hirota et al.
Nucleic acids symposium series, (34)(34), 15-16 (1995-01-01)
It is reported that the diisobutylaluminum hydride (DIBALH) reduction of inosine and adenosine derivatives (1a and 1d) causes cleavage of the ribose moiety to give the corresponding 9-ribitylhypoxanthine (2a) and 9-ribityladenine (2d), respectively. The substitution effect of purine nucleosides on
Carl A Busacca et al.
The Journal of organic chemistry, 73(4), 1524-1531 (2008-01-17)
The reduction of tertiary phosphine oxides (TPOs) and sulfides with diisobutylaluminum hydride (DIBAL-H) has been studied in detail. An extensive solvent screen has revealed that hindered aliphatic ethers, such as MTBE, are optimum for this reaction at ambient temperature. Many
A direct entry to substituted N-methoxyamines from N-methoxyamides via N-oxyiminium ions.
Kenji Shirokane et al.
Angewandte Chemie (International ed. in English), 49(36), 6369-6372 (2010-07-31)
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