Diisobutylhydroaluminum

Base Information

• Chemical Name: Diisobutylhydroaluminum
• CAS No.: 1191-15-7
• Molecular Formula: C8H19Al
• Molecular Weight: 142.22
• Hs Code.: 29319090
• DSSTox Substance ID: DTXSID4041866
• Wikidata: Q420788
• Mol file: 1191-15-7.mol

Synonyms:DiBAlH;Al-Alchili;iBu2AlH;(iBu)2AlH;hydrido(diisobutyl)aluminum;UNII-H2EJ47H11A;DTXSID4041866;Diisobutylaluminum hydride 1M in Hexane;Diisobutylaluminum hydride, reagent grade;EC 214-729-9;Q420788

Chemical Property of Diisobutylhydroaluminum

Chemical Property:

• Appearance/Colour: Clear solution
• Vapor Pressure: 13.3Pa at 90℃
• Melting Point: -70 °C
• Boiling Point: 110 °C
• Flash Point: 4 °C
• PSA: 0.00000
• Density: 0.848 g/cm³
• LogP: 3.33250
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive/Heat Sensitive
• Solubility.: Miscible with organic solvents.
• Water Solubility.: vigorous reaction
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 4
• Exact Mass: 142.1302140
• Heavy Atom Count: 9
• Complexity: 49.6

Purity/Quality:

98% ^*data from raw suppliers

Di-i-butylaluminum hydride (20% in hexanes) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,F,C,N
• Hazard Codes: F,T,C,N
• 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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)C[AlH]CC(C)C
• 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.
• 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. Diisobutylaluminum hydride is used as reducing agent in pharmaceuticals. It is also used as raw material in organic synthesis, agrochemicals and dyestuffs. 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.

Technology Process of Diisobutylhydroaluminum

There total 6 articles about Diisobutylhydroaluminum which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

→ diisobutylaluminium hydride (1191-15-7)

Guidance literature:

Reference yield:

diethyl ether (60-29-7,927820-24-4) + water (7732-18-5) → diisobutylaluminium hydride (1191-15-7)

Guidance literature:

With hydrogenchloride; diisobutylaluminium hydride; In tetrahydrofuran; methanol;

Reference yield:

[rac-1,2-ethylene-bis(η5-4,5,6,7-tetrahydroindenyl)]dichloridezirconium(IV) + diisobutylaluminum chloride (1779-25-5) → rac-C2H4(4,5,6,7-tetrahydroindenyl)2ZrCl(μ-H)2Al(i-Bu)2 + rac-C2H4(4,5,6,7-tetrahydroindenyl)2ZrH(μ-H)2Al(i-Bu)2 + diisobutylaluminium hydride (1191-15-7)

Guidance literature:

In ⁽²⁾H₈-toluene; toluene-d7, 1 equiv of Al-compound, 25°C; not sepd., detected by NMR spectra;

DOI:10.1021/ja8054723

upstream raw materials:

triisobutylaluminum

diethyl ether

water

diisobutylaluminum chloride

Downstream raw materials:

(4S,5R)-4-(cyclohexylmethyl)-2-oxo-5-oxazolidinecarboxaldehyde

(3S)-3-((S)-4-methyl-2-phenylsulfonylaminovalerylamino)-2-tetrahydrofuranol

diisobutylaluminum chloride

N-(diisobutylaluminum)benzaldehyde imine

Refernces

• 1、 -. "Inhibitors of histone deacetylase". . . Retrieved 2008/06/13.
• 2、 -. "Pyronin antibacterials, process and novel intermediates thereto". . . Retrieved 2008/06/13.