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190306

Sigma-Aldrich

Diisobutylaluminum hydride solution

1.0 M in hexanes

Sinônimo(s):

DIBAL, DIBAL-H

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About This Item

Fórmula linear:
[(CH3)2CHCH2]2AlH
Número CAS:
1191-15-7
Peso molecular:
142.22
Beilstein:
4123663
Número MDL:
MFCD00008928
Código UNSPSC:
12352001
ID de substância PubChem:
24851429
NACRES:
NA.22
Preço e disponibilidade não estão disponíveis no momento.

Formulário

liquid

Nível de qualidade

200

adequação da reação

reagent type: reductant

concentração

1.0 M in hexanes

densidade

0.701 g/mL at 25 °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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Descrição geral

Diisobutylaluminum hydride reducing agent is commonly used for the reduction of an ester to aldehyde.[1]

Aplicação

Diisobutylaluminum hydride solution (1.0 M in hexanes) can be used in the synthesis of potassium diisobutyl-t-butoxyaluminum hydride (PDBBA), a novel reducing agent for the chemoselective conversion of esters in the presence of nitriles.[1] The DIBAL-triethylamine complex can reduce α-oxoketene dithioacetal to the saturated ketone.[2]
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

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

Órgãos-alvo

Central nervous system, Nervous system

Perigos de suplementos

EUH014

Código de classe de armazenamento

4.2 - Pyrophoric and self-heating hazardous materials

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

-9.4 °F - closed cup

Ponto de fulgor (°C)

-23 °C - closed cup

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Certificados de análise (COA)

Lot/Batch Number
SHBS6725
SHBR6650
STBL3842
STBL4784
STBL2310

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alpha.-Oxoketene dithioacetal chemistry. 2. Conjugate reductions with electrophilic reducing agents.
Gammill R
The Journal of Organic Chemistry, 46(17), 3555-3558 (1981)
Chemoselective Reduction of Esters to Aldehydes by Potassium Diisobutyl-t-butoxyaluminum Hydride (PDBBA).
Chae MJ, et al.
Bull. Korean Chem. Soc., 28(12), 2517-2517 (2007)
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
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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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    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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