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Sigma-Aldrich

Diisobutylaluminum hydride

reagent grade

Synonym(s):

DIBAL, DIBAL-H

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About This Item

Linear Formula:
[(CH3)2CHCH2]2AlH
CAS Number:
Molecular Weight:
142.22
Beilstein:
4123663
EC Number:
MDL number:
UNSPSC Code:
12352001
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

grade

reagent grade

reaction suitability

reagent type: reductant

bp

116-118 °C/1 mmHg (lit.)

density

0.798 g/mL at 25 °C (lit.)

SMILES string

[H][Al](CC(C)C)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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General description

Diisobutylaluminum hydride is commonly used as a reducing agent in organic synthesis.[1]

Application

Diisobutylaluminum hydride can be used in the following protocols:
  • As a promotor of Tishchenko reaction of aldehydes.[2]
  • Conversion of benzylidene acetals of 1,2-and 1,3-glycols to the corresponding monobenzyl ethers of the glycols.[3]
  • To generate a novel chiral reducing agent based on (S)-proline for the asymmetric reduction of prochiral ketones.[4]

Packaging

Supplied in a Sure/Pac cylinder and has a 1/4-turn bronze ball valve with a female 1/4" NPT outlet thread (Z122661) installed. Before using the cylinder, ensure that the valve is closed, then remove carbon steel plug that seals the outlet valve.

Compatible with the following:
For instructions please refer to technical bulletin AL-136: The Aldrich Sure/Pac Cylinder System

Legal Information

Aldrich is a registered trademark of Sigma-Aldrich Co. LLC
Sure/Pac is a trademark of Sigma-Aldrich Co. LLC

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Pictograms

FlameCorrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Eye Dam. 1 - Pyr. Liq. 1 - Skin Corr. 1B - Water-react 1

Supplementary Hazards

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

nwg

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number

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Asymmetric reduction of prochiral keto esters with a chiral reducing agent prepared from tin (II) chloride, chiral diamine, and diisobutylaluminum hydride.
Mukaiyama T, et al.
Chemistry Letters (Jpn), 14(6), 813-816 (1985)
Daisuke Ando et al.
Journal of agricultural and food chemistry, 66(39), 10154-10162 (2018-09-13)
The metabolic fate of a new fungicide, mandestrobin, labeled with 14C at the phenoxy or benzyl ring was examined in wheat after a single spray application at 300 g/ha. Mandestrobin penetrated into foliage over time, with both radiolabels showing similar
Tishchenko reactions of aldehydes promoted by diisobutylaluminum hydride and its application to the macrocyclic lactone formation.
Hon YS, et al.
Tetrahedron, 63(46), 11325-11340 (2007)
A facile cleavage of benzylidene acetals with diisobutylaluminum hydride.
Takano S, et al.
Chemistry Letters (Jpn), 12(10), 1593-1596 (1983)
Reaction of diisobutylaluminum hydride with selected organic compounds containing representative functional groups
Yoon N M
The Journal of Organic Chemistry, 50(14), 2443-2450 (1985)

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

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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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