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190306

Sigma-Aldrich

Idruro di diisobutilalluminio

1.0 M in hexanes

Sinonimo/i:

DIBAL, DIBAL-H

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About This Item

Formula condensata:
[(CH3)2CHCH2]2AlH
Numero CAS:
1191-15-7
Peso molecolare:
142.22
Beilstein:
4123663
Numero MDL:
MFCD00008928
Codice UNSPSC:
12352001
ID PubChem:
24851429
NACRES:
NA.22
Prezzi e disponibilità al momento non sono disponibili

Stato

liquid

Livello qualitativo

200

Impiego in reazioni chimiche

reagent type: reductant

Concentrazione

1.0 M in hexanes

Densità

0.701 g/mL at 25 °C

Stringa SMILE

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

InChI

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

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Categorie correlate

Descrizione generale

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

Applicazioni

Utilizzato nella debrominazione riduttiva degli alchil bromuri secondari catalizzata da Pd. O-debenzilazione e apertura dell′anello di furanosidi perbenzilati. Comoda generazione in situ di HZrCp2Cl da ZrCp2Cl2 e DIBAL-H.
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]

Avvertenze

Danger

Classi di pericolo

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

Organi bersaglio

Central nervous system, Nervous system

Rischi supp

EUH014

Codice della classe di stoccaggio

4.2 - Pyrophoric and self-heating hazardous materials

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

-9.4 °F - closed cup

Punto d’infiammabilità (°C)

-23 °C - closed cup

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Certificati d'analisi (COA)

Lot/Batch Number
SHBS6725
SHBR6650
STBL3842
STBL4784
STBL2310

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Supelco

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Sigma-Aldrich

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Copper(I) iodide for synthesis

Sigma-Aldrich

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1-Pentyne 99%

Sigma-Aldrich

256560

1-Pentyne

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)
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
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
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Questions

1–2 of 2 Questions  

  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

      Helpful?

  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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