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Diisobutylaluminum hydride solution

1.0 M in cyclohexane

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Synonym(s):
DIBAL, DIBAL-H
Linear Formula:
[(CH3)2CHCH2]2AlH
CAS Number:
Molecular Weight:
142.22
Beilstein/REAXYS Number:
4123663
MDL number:
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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1 of 4

This Item
214981214965190306
Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

200

density

0.781 g/mL at 25 °C

density

0.866 g/mL at 25 °C

density

0.731 g/mL at 25 °C

density

0.701 g/mL at 25 °C

form

liquid

form

liquid

form

liquid

form

liquid

concentration

1.0 M in cyclohexane

concentration

1.0 M in THF

concentration

1.0 M in heptane

concentration

1.0 M in hexanes

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.

signalword

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

supp_hazards

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

wgk_germany

WGK 3

flash_point_f

1.4 °F - closed cup

flash_point_c

-17 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter


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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)
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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