DIBAL-H

(Diisobutylaluminum hydride)

Other Names:

DIBALH

DIBAL

General Information:

Structure:

CAS Number: 1191-15-7

Molecular Weight: 142.22 g/mol

Appearance: Colorless liquid

Diisobutylaluminum hydride (DIBAL-H) is an organoaluminum reagent typically used for the reduction esters or nitriles to aldehydes. DIBAL-H is usually obtained and used as a 1.0 M solution in a wide variety of solvents (ex. DCM, THF, hexanes, heptane, toluene, and cyclohexane). Some of the advantages of using DIBAL-H over other organoaluminum reagents include its greater selectivity, its ease of handing as a liquid, and its miscibility with a wide range of solvents (including hydrocarbons and aromatic solvents).

Common Uses:

Reagent for reducing esters to aldehydes

Reagent for reducing esters to alcohols

Procedure excerpt:

To a stirred solution of the SM (5 g, 21.8 mmol) in toluene (50 mL) was added DIBAL-H (43.6 mL, 43.6 mmol) at 0 C. The reaction mixture was stirred . . .

[full procedure]

Reagent for reducing nitriles to aldehydes

Procedure excerpt:

. . . purged with N2 and cooled to -64 C. Under N2 atmsophere, was added DIBAL-H (1.0M in hexane, 2.6 mL, 2.6 mmol). The mixture was stirred at -64 C for 2 h. While maintaining . . .

[full procedure]

Reagent for reducing nitriles to amines

Safety:

Diisobutylaluminum hydride (DIBAL-H) reacts violently with water and moisture in the air (pyrophoric).

References:

1) Patent Reference: WO2015140133, page 106, (11.7 MB)

2) Patent Reference: WO2015129926, page 111, (21.5 MB)

3) www.akzonobel.com: Diisobutylaluminum hydride (DIBAL-H) and Other Isobutyl Aluminum Alkyls (DIBAL-BOT, TIBAL) as Specialty Organic Synthesis Reagents (link)

4) Burke, S. D.; Danheiser, R. L.; Handbook of Reagents for Organic Synthesis, Oxidizing and Reducing Agents

5) Wikipedia: Diisobutylaluminium hydride (link)

6) www.sigmaaldrich.com: Diisobutylaluminum hydride solution - 1.0 M in methylene chloride (link)