256811
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
Recommended Products
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:
Compatible with the following:
- Aldrich® Sure/Pac™ station for liquefied gases Z566446
- PTFE Sealing tape Z104388 or Z221880
- Straight septum-inlet adapter Z118141 with septa Z565687 or Z565695.
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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recommended
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septum inlet adapter
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Signal Word
Danger
Hazard Statements
Precautionary 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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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)
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
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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