256811

Sigma-Aldrich

Diisobutylaluminum hydride

reagent grade

Synonym(s):
DIBAL, DIBAL-H
Linear Formula:
(CH3)2CHCH22AlH
CAS Number:
Molecular Weight:
142.22
Beilstein/REAXYS Number:
4123663
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

grade

reagent grade

bp

116-118 °C/1 mmHg (lit.)

density

0.798 g/mL at 25 °C (lit.)

SMILES string

HAl(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

100 g in Sure-Pac™
1 kg in Sure-Pac™

Recommended products

Angled septum-inlet adapter Z118206 or straight septum-inlet adapter, 6mm I.D. inlet, Z118141 or straight septum-inlet adapter, 13mm I.D. inlet, Z118192 is recommended.

Pictograms

FlameCorrosion

Signal Word

Danger

Hazard Statements

Supp Hazards

EUH014

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

F,C

Risk Statement

14/15-17-35

Safety Statement

26-36/37/39-43-45

RIDADR

UN 3394 4.3(4.2) / PGI

WGK Germany

nwg

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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)
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)
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...

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