Diisobutylaluminium hydride Chemical Properties

Melting point:

-70 °C

Boiling point:

65 °C

Density 

1.23 g/mL at 25 °C

vapor pressure 

13.3Pa at 90℃

Flash point:

40 °F

storage temp. 

2-8°C

solubility 

Miscible with organic solvents.

form 

Solution

Specific Gravity

0.860

color 

Clear

Water Solubility 

vigorous reaction

Hydrolytic Sensitivity

8: reacts rapidly with moisture, water, protic solvents

Sensitive 

Air Sensitive/Heat Sensitive

BRN 

4123663

Exposure limits

ACGIH: TWA 20 ppm
OSHA: Ceiling 300 ppm; TWA 200 ppm
NIOSH: IDLH 500 ppm; TWA 100 ppm(375 mg/m3); STEL 150 ppm(560 mg/m3)

InChIKey

AZWXAPCAJCYGIA-UHFFFAOYSA-N

LogP

4.22

CAS DataBase Reference

1191-15-7(CAS DataBase Reference)

NIST Chemistry Reference

Diisobutylaluminum hydride(1191-15-7)

EPA Substance Registry System

Diisobutylaluminum hydride (1191-15-7)

Safety Information

Hazard Codes 

F,T,C,N

Risk Statements 

14/15-17-35-40-67-65-63-48/20-11-34-19-62-51/53-23/24/25-20/21/22-15-14-50/53-37-22

Safety Statements 

26-43-45-62-46-36/37/39-29-16-61-27-9

RIDADR 

UN 3399 4.3/PG 1

WGK Germany 

2

RTECS 

BD0710000

F 

1-4.3-10

TSCA 

Yes

HazardClass 

4.3

PackingGroup 

I

HS Code 

29319090

Hazardous Substances Data

1191-15-7(Hazardous Substances Data)

MSDS

• Language:English Provider:Diisobutylaluminium hydride
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Diisobutylaluminium hydride Usage And Synthesis

Description

Diisobutylaluminium hydride (DIBALH, DIBAL, DIBAL-H or DIBAH) is a reducing agent with the formula (i-Bu2AlH)2, where i-Bu represents isobutyl (-CH2CH(CH3)2). It can be used for various homogeneous reductions such as alkynes to alkenes, esters or nitriles to aldehydes. It is available commercially as the neat reagent and as a solution in several different solvents (hexane, dichloromethane, tetrahydrofuran, etc.). The neat reagent is a liquid and is supplied in metal cylinders. It is pyrophoric and highly reactive and therefore must be handled with great care. The molar solutions in organic solvents are more stable and easier to handle provided that the normal precautions are taken for working with air-sensitive compounds. They must all be handled in an atmosphere free from oxygen and water. Commonly used solvents for diisobutylaluminium hydride are dichloromethane, diglyme, dioxane and tetrahydrofuran. Even when the substrate is not completely soluble in these solvents successful reductions can be accomplished.

Chemical Properties

Diisobutylaluminium hydride, also known as Dibal. colorless liquid. Viscosity 18.0mPa-s(25℃). Reacts violently with water to form hydrogen and isobutane. Tetrahydrofuran is not suitable as Dibal solvent, because the two react to produce coordination compounds. Diisobutylaluminium hydride is a useful reducing agent in organic synthesis. It can reduce ketones, carboxylic acids and esters to the corresponding alcohols. Dibal can also reduce lactones to o-hydroxy lactones.

Uses

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

Uses

Diisobutylaluminum hydride is used as reducing agent in pharmaceuticals. It is also used as raw material in organic synthesis, agrochemicals and dyestuffs.

Uses

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.

Flammability and Explosibility

Spontaneously flammable in air (pyrophoric)

Safety Profile

Mddly toxic by inhalation. Dangerous fire hazard; iptes spontaneously in air. To fight fire, do not use water, foam, or halogenated extinguisking agents. See also HYDRIDES and ALUMINUM COMPOUNDS.

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