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214981

Sigma-Aldrich

Diisobutylaluminum hydride solution

1.0 M in THF

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/REAXYS Number:
4123663
MDL number:
MFCD00008928
UNSPSC Code:
12352001
eCl@ss:
38120609
PubChem Substance ID:
24852859
NACRES:
NA.22

form

liquid

Quality Level

200

reaction suitability

reagent type: reductant

concentration

1.0 M in THF

bp

65 °C

density

0.866 g/mL at 25 °C

storage temp.

2-8°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 THF) is a powerful reducing agent. It can be used in the following reactions:
  • Synthesis of trans-alkene isosteres of protected dipeptides.
  • To generate bis(1,5-cyclooctadiene)nickel(0) (Ni(cod)2) in situ, which can catalyze the conjugate addition of ethenyltributyltin to 2-propenal to form tert-butyldimethyl[((E)-1,4pentadienyl)oxy]silane.
  • Reduction of the arylpropiolate esters to give the corresponding propargyl 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.

Packaging

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Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Pyr. Liq. 1 - Skin Corr. 1B - STOT SE 3 - Water-react 1

target_organs

Central nervous system, Respiratory system

supp_hazards

EUH014,EUH019

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

wgk_germany

WGK 1

flash_point_f

1.4 °F - closed cup

flash_point_c

-17 °C - closed cup

ppe

Faceshields, Gloves, Goggles

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR2434
SHBR0979
SHBR0978
STBK5189
STBK1428

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A stereocontrolled synthesis of trans-alkene isosteres of dipeptides.
Spaltenstein A, et al.
Tetrahedron Letters, 27(19), 2095-2098 (1986)
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
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
Y Kitade et al.
Nucleic acids symposium series, (27)(27), 107-108 (1992-01-01)
Reaction of purine nucleosides, such as 2',3'-isopropylideneinosine (1a) and 2',3'-isopropylideneadenosine (1c), with diisobutylaluminum hydride (DIBAL) in dry tetrahydrofurane resulted in the formation of the corresponding 9-(2',3'-isopropylideneribity)purines (2) in good yields. Oxidation of the ribityl derivatives (2) with NalO4 and subsequent
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