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214949

Sigma-Aldrich

Diisobutylaluminum hydride solution

1.0 M in cyclohexane

Synonym(s):

DIBAL, DIBAL-H

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About This Item

Linear Formula:
[(CH3)2CHCH2]2AlH
CAS Number:
Molecular Weight:
142.22
Beilstein:
4123663
MDL number:
UNSPSC Code:
12352001
eCl@ss:
38120609
PubChem Substance ID:
NACRES:
NA.22

form

liquid

reaction suitability

reagent type: reductant

concentration

1.0 M in cyclohexane

density

0.781 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 (DIBAL-H) can be used as a reducing agent in the:
  • Hydrogenation of ester modified hydroxyl-terminated polybutadiene (HTPB) using cobalt catalyst.
  • Synthesis of primary 6-OH alcohols by regioselective ring opening of 4,6-benzylidene acetals of hexopyranosides using triphenylcarbenium tetrafluoroborate as a catalyst.
  • Conversion of an ester to 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.

Signal Word

Danger

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Pyr. Liq. 1 - Skin Corr. 1B - STOT SE 3 - Water-react 1

Target Organs

Central nervous system

Supplementary Hazards

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 3

Flash Point(F)

1.4 °F - closed cup

Flash Point(C)

-17 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Synthesis and transannular Diels-Alder reaction of a cis-trans-trans and a trans-cis-cis 13-membered macrocyclic trienone
Marinier A, et al.
Canadian Journal of Chemistry, 67(10), 1609-1617 (1989)
Triphenylcarbenium Tetrafluoroborate as an Efficient Catalyst in the Regioselective Reductive Ring Opening of Benzylidene Acetals of Carbohydrates
Thota N, et al.
ChemistrySelect, 4(27), 7976-7980 (2019)
Determination of the hydrogenation degree of telechelic polybutadiene by 1HNMR
Lira CH, et al.
Magnetic Resonance in Chemistry, 5, 22-22 (2006)
Thomas Lecourt et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 10(12), 2960-2971 (2004-06-24)
To explain the remarkable regioselective de-O-benzylating properties of diisobutylaluminium hydride (DIBAL-H) and triisobutylaluminium (TIBAL) towards polybenzylated sugars or cyclodextrins, we propose a plausible mechanistic rationale critically involving the kinetic formation of a product-generating 2:1 Al-benzylated sugar complex. For the reaction
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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