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214981

Sigma-Aldrich

Diisobutylaluminiumhydrid -Lösung

Diisobutylaluminum hydride solution

1.0 M in THF

Synonym(e):

DIBAH, DIBAL

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About This Item

Lineare Formel:
[(CH3)2CHCH2]2AlH
CAS-Nummer:
Molekulargewicht:
142.22
Beilstein:
4123663
MDL-Nummer:
UNSPSC-Code:
12352001
eCl@ss:
38120609
PubChem Substanz-ID:
NACRES:
NA.22
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Form

liquid

Qualitätsniveau

Eignung der Reaktion

reagent type: reductant

Konzentration

1.0 M in THF

bp

65 °C

Dichte

0.866 g/mL at 25 °C

Lagertemp.

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;;

InChIKey

AZWXAPCAJCYGIA-UHFFFAOYSA-N

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Anwendung

Diisobutylaluminiumhydrid-Lösung (1 M in THF) ist ein leistungsstarkes Reduktionsmittel. Es kann in den folgenden Reaktionen eingesetzt werden:
  • Synthese von trans-Alkenisosteren geschützter Dipeptide.
  • Zur Erzeugung von Bis(1,5-cyclooctadien)nickel(0) (Ni(cod)2) in situ, welche die Konjungataddition von Ethenyltributyltin an 2-Propenal katalysieren kann, um tert-Butyldimethyl[((E)-1,4-pentadienyl)oxy]silan zu bilden.
  • Reduktion von Arylpropiolatestern, um den entsprechenden Propargylalkohol zu erhalten.

Wird in der Pd-katalysierten reduktiven Debrominierung sekundärer Alkylbromide eingesetzt. O-Debenzylierung und Ringöffnung perbenzylierter Furanoside. Praktische In-situ-Bildung von HZrCp2Cl aus ZrCp2Cl2 und DIBAL-H.

Verpackung

Signalwort

Danger

Gefahreneinstufungen

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

Zielorgane

Central nervous system, Respiratory system

Zusätzliche Gefahrenhinweise

Lagerklassenschlüssel

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 1

Flammpunkt (°F)

1.4 °F - closed cup

Flammpunkt (°C)

-17 °C - closed cup

Persönliche Schutzausrüstung

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

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    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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    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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