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214965

Sigma-Aldrich

Diisobutylaluminum hydride solution

1.0 M in heptane

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
MDL number:
MFCD00008928
UNSPSC Code:
12352001
PubChem Substance ID:
24852857
NACRES:
NA.22

form

liquid

Quality Level

200

reaction suitability

reagent type: reductant

concentration

1.0 M in heptane

density

0.731 g/mL at 25 °C

SMILES string

CC(C)C[AlH]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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Application

Diisobutylaluminum hydride (DIBAL-H) is a common reducing agent to reduce aldehydes, ketones, esters, acids and acid chlorides to the corresponding alcohols. Some of the applications are:
  • Synthesis of α-acetoxy ethers by reduction and subsequent acetylation of esters.
  • Synthesis of coniferyl, sinapyl, and p-coumaryl alcohol by selective reduction of corresponding cinnamate esters.
  • Reduction of secondary phosphine oxides (SPOs) to the corresponding phosphines.
  • DIBAL-H can also be used in the hydroalumination of alkene and alkynes.

Used in Pd-catalyzed reductive debromination of secondary alkyl bromides. O-Debenzylation and ring opening of perbenzylated furanosides. Convenient in situ generation of HZrCp2Cl from ZrCp2Cl2 and DIBAL-H.

Signal Word

Danger

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Pyr. Liq. 1 - Skin Corr. 1B - STOT SE 3 - Water-react 1

Target Organs

Central nervous system

Supplementary Hazards

EUH014

WGK

WGK 2

Flash Point(F)

30.2 °F

Flash Point(C)

-1 °C

Regulatory Information

新产品

Certificates of Analysis (COA)

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General Synthesis of α-Acetoxy Ethers from Esters by DIBALH Reduction and Acetylation.
Dahanukar V H and Rychnovsky S D
The Journal of Organic Chemistry, 61(23), 8317-8320 (1996)
Applications of diisobutylaluminium hydride (DIBAH) and triisobutylaluminium (TIBA) as reducing agents in organic synthesis.
Winterfeldt E
Synthesis, 1975(09), 617-630 (1975)
A Superior method for the reduction of secondary phosphine oxides.
Busacca C A, et al.
Organic Letters, 7(19), 4277-4280 (2005)
Facile large-scale synthesis of coniferyl, sinapyl, and p-coumaryl alcohol.
Quideau S and Ralph J.
Journal of Agricultural and Food Chemistry, 40(7), 1108-1110 (1992)
Organometallic compounds of Group III. XIX. Regiospecificity and stereochemistry in the hydralumination of unsymmetrical acetylenes. Controlled cis or trans reduction of 1-alkynyl derivatives.
Eisch J J and Foxton M W
The Journal of Organic Chemistry, 36(23), 3520-3526 (1971)
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