1191-15-7 Usage
Description
Diisobutylaluminium hydride (DIBALH, DIBAL, DIBAL-H, or DIBAH) is a colorless liquid with the chemical formula (i-Bu2AlH)2, where i-Bu represents isobutyl (-CH2CH(CH3)2). It is a highly reactive reducing agent used for various homogeneous reductions, such as converting alkynes to alkenes, esters, or nitriles to aldehydes. It is pyrophoric and must be handled with great care in an atmosphere free from oxygen and water.
Uses
Diisobutylaluminium hydride is used as a reducing agent in various applications across different industries. Some of its uses include:
1. Used in Organic Synthesis:
Diisobutylaluminium hydride is used as a reducing agent for the following protocols:
As a promotor of Tishchenko reaction of aldehydes.
Conversion of benzylidene acetals of 1,2and 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. Used in Pharmaceutical Industry:
Diisobutylaluminium hydride is used as a reducing agent in the synthesis of various pharmaceutical compounds.
3. Used in Agrochemicals and Dye Industry:
Diisobutylaluminium hydride is used as a raw material in the synthesis of agrochemicals and dyestuffs.
4. Used in the Synthesis of α-Acetoxy Ethers:
Diisobutylaluminium hydride is used to reduce and subsequently acetylate esters to produce α-acetoxy ethers.
5. Used in the Synthesis of Coniferyl, Sinapyl, and p-Coumaryl Alcohol:
Diisobutylaluminium hydride is used for the selective reduction of corresponding cinnamate esters to synthesize coniferyl, sinapyl, and p-coumaryl alcohol.
6. Used in the Reduction of Secondary Phosphine Oxides (SPOs):
Diisobutylaluminium hydride is used to reduce SPOs to the corresponding phosphines.
7. Used in the Hydroalumination of Alkene and Alkynes:
Diisobutylaluminium hydride can also be used in the hydroalumination of alkene and alkynes.
Chemical Properties:
Diisobutylaluminium hydride, also known as Dibal, has a viscosity of 18.0 mPa-s at 25℃. It reacts violently with water to form hydrogen and isobutane. Tetrahydrofuran is not suitable as a Dibal solvent, as the two react to produce coordination compounds. Dibal is a useful reducing agent in organic synthesis, capable of reducing ketones, carboxylic acids, and esters to the corresponding alcohols. It can also reduce lactones to o-hydroxy lactones.
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).