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Merck

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

Key Documents

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Product Name

Diisobutylaluminum hydride solution, 1.0 M in toluene

InChI

1S/2C4H9.Al.H/c2*1-4(2)3;;/h2*4H,1H2,2-3H3;;

SMILES string

CC(C)C[AlH]CC(C)C

InChI key

AZWXAPCAJCYGIA-UHFFFAOYSA-N

form

liquid

reaction suitability

reagent type: reductant

concentration

1.0 M in toluene

density

0.858 g/mL at 25 °C

Quality Level

200

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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

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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

supp_hazards

EUH014

Storage Class

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

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Certificates of Analysis (COA)

Lot/Batch Number
SHBT4594
SHBT1585
SHBT1584
SHBS3614
SHBR6962

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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)
Takashi Tomioka et al.
The Journal of organic chemistry, 76(11), 4669-4674 (2011-04-30)
Stepwise, selective DIBAL reduction of the acetonide diester derived from tartaric acid followed by the Horner-Emmons reaction effectively provided desymmetrized hydroxy mono-olefination products in a one-pot operation.
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
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