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MilliporeSigma

214981

Sigma-Aldrich

Hidruro de diisobutilaluminio solution

1.0 M in THF

Sinónimos:

DIBAL, DIBAL-H

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About This Item

Fórmula lineal:
[(CH3)2CHCH2]2AlH
Número de CAS:
Peso molecular:
142.22
Beilstein/REAXYS Number:
4123663
MDL number:
UNSPSC Code:
12352001
eCl@ss:
38120609
PubChem Substance ID:
NACRES:
NA.22

form

liquid

Quality Level

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.

Utilizada en la desbromación reductiva catalizada por Pd de los alquil bromuros secundarios. O-desbencilación y apertura del anillo de los furanósidos perbencilados. Cómoda generación in situ de HZrCp2Cl a partir de ZrCp2Cl2 y DIBAL-H.

signalword

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

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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A stereocontrolled synthesis of trans-alkene isosteres of dipeptides.
Spaltenstein A, et al.
Tetrahedron Letters, 27(19), 2095-2098 (1986)
Damien Webb et al.
Organic letters, 14(2), 568-571 (2011-12-31)
A continuous flow system for the multiparameter (flow rate, temperature, residence time, stoichiometry) optimization of the DIBALH reduction of esters to aldehydes is described. Incorporating an in-line quench (MeOH), these transformations are generally complete in fewer than 60 s. Mixing
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
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
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

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