1191-15-7 Usage
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
Different sources of media describe the Uses of 1191-15-7 differently. You can refer to the following data:
1. 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.
2. Diisobutylaluminum hydride is used as reducing agent in pharmaceuticals. It is also used as raw material in organic synthesis, agrochemicals and dyestuffs.
3. 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
Spontaneouslyflammableinair(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.
Check Digit Verification of cas no
The CAS Registry Mumber 1191-15-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,1,9 and 1 respectively; the second part has 2 digits, 1 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 1191-15:
(6*1)+(5*1)+(4*9)+(3*1)+(2*1)+(1*5)=57
57 % 10 = 7
So 1191-15-7 is a valid CAS Registry Number.
InChI:InChI=1/2C4H9.Al.H/c2*1-4(2)3;;/h2*4H,1H2,2-3H3;;/q;;+1;-1/rC8H18Al.H/c1-7(2)5-9-6-8(3)4;/h7-8H,5-6H2,1-4H3;/q+1;-1
1191-15-7Relevant articles and documents
Alkylaluminum-complexed zirconocene hydrides: Identification of hydride-bridged species by NMR spectroscopy
Baldwin, Steven M.,Bereaw, John E.,Brintzinger, Hans H.
, p. 17423 - 17433 (2009/06/08)
Reactions of unbridged zirconocene dichlorides, (RnC 5H5-n)2ZrCl2 (n=0, 1, or 2), with diisobutylaluminum hydride (HAI'Bu2) result in the formation of tetranuclear trihydride clusters of the type (RnC5H 5-n)2Zr(μ-H)3(Al iBu2)3(μ-CI) 2, which contain three [Al iBu2] units. Ring-bridged ansa-zirconocene dichlorides, Me2E(RnC5H 4-n)2ZrCl2 with E=C or Si, on the other hand, are found to form binuclear dihydride complexes of the type Me2E(R nC5H4-n)2Zr(CI)(μ-H) 2Al iBu2 with only one [AIBu2] unit. The dichotomy between unbridged and bridged zirconocene derivatives with regard to tetranuclear versus binuclear product formation is proposed to be connected to different degrees of rotational freedom of their C5-ring ligands. Alkylaluminum-complexed zirconocene dihydrides, previously observed in zirconocene-based precatalyst systems activated by methylalumoxane (MAO) upon addition of HAI'Bu2 or Al iBu3, are proposed to be species of the type Me2Si(ind)2Zr(Me)(μ-H) 2Al iBu2, stabilized by interaction of their terminal Me group with a Lewis acidic site of MAO.
Pyronin antibacterials, process and novel intermediates thereto
-
, (2008/06/13)
The present invention provides convergent processes for preparing myxopyronins and corallopyronins, compounds useful as antibacterial therapeutics. The present invention also provides novel compositions of matter which are useful for the preparation of pyronin antibiotics.
Aminediol protease inhibitors
-
, (2008/06/13)
Novel aminediol compounds, pharmaceutical compositions containing these compounds, and methods of using these compounds in inhibiting retroviral protease, particularly useful in the treatment and/or prevention of HIV infection (AIDS).