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Sigma-Aldrich

Diisobutylaluminum hydride solution

Diisobutylaluminum hydride solution

1.0 M in THF

Sinônimo(s):

DIBAL, DIBAL-H

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About This Item

Fórmula linear:
[(CH3)2CHCH2]2AlH
Número CAS:
Peso molecular:
142.22
Beilstein:
4123663
Número MDL:
Código UNSPSC:
12352001
eCl@ss:
38120609
ID de substância PubChem:
NACRES:
NA.22
Preço e disponibilidade não estão disponíveis no momento.

Formulário

liquid

Nível de qualidade

adequação da reação

reagent type: reductant

concentração

1.0 M in THF

p.e.

65 °C

densidade

0.866 g/mL at 25 °C

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

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

InChI

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

chave InChI

AZWXAPCAJCYGIA-UHFFFAOYSA-N

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Aplicação

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.

Palavra indicadora

Danger

Classificações de perigo

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

Órgãos-alvo

Central nervous system, Respiratory system

Perigos de suplementos

Código de classe de armazenamento

4.2 - Pyrophoric and self-heating hazardous materials

Classe de risco de água (WGK)

WGK 1

Ponto de fulgor (°F)

1.4 °F - closed cup

Ponto de fulgor (°C)

-17 °C - closed cup

Equipamento de proteção individual

Faceshields, Gloves, Goggles


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Nickel-catalyzed, chlorotrialkylsilane-assisted conjugate addition of alkenyltributyltin reagents to. alpha.,. beta.-unsaturated aldehydes. Evidence for a [1-[(trialkylsilyl) oxy] allyl] nickel (II) mechanism.
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Journal of the American Chemical Society, 114(13), 5160-5165 (1992)
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
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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    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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