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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:
1191-15-7
Molecular Weight:
142.22
Beilstein:
4123663
EC Number:
214-729-9
MDL number:
MFCD00008928
UNSPSC Code:
12352001
PubChem Substance ID:
24855552
NACRES:
NA.22

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.

Application

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

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
GHS02,GHS05

Signal Word

Danger

Hazard Statements

H250,H260,H314

Hazard Classifications

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

Supplementary Hazards

EUH014

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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