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Merck
CN

256811

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
UNSPSC Code:
12352001
NACRES:
NA.22
PubChem Substance ID:
24855552
EC Number:
214-729-9
Beilstein/REAXYS Number:
4123663
MDL number:
MFCD00008928

Key Documents

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Product Name

Diisobutylaluminum hydride, reagent grade

InChI key

AZWXAPCAJCYGIA-UHFFFAOYSA-N

InChI

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

SMILES string

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

grade

reagent grade

reaction suitability

reagent type: reductant

bp

116-118 °C/1 mmHg (lit.)

density

0.798 g/mL at 25 °C (lit.)

Quality Level

100

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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.

General description

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

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

pictograms

FlameCorrosion
GHS02,GHS05

signalword

Danger

Hazard Classifications

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

supp_hazards

EUH014

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

wgk

nwg

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SHBT2641
SHBS4352
SHBS3773
SHBQ0206
SHBM9369

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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)
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)
A facile cleavage of benzylidene acetals with diisobutylaluminum hydride.
Takano S, et al.
Chemistry Letters (Jpn), 12(10), 1593-1596 (1983)
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
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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