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Merck
모든 사진(3)

Key Documents

190306

Sigma-Aldrich

Diisobutylaluminum hydride solution

1.0 M in hexanes

동의어(들):

DIBAL, DIBAL-H

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About This Item

Linear Formula:
[(CH3)2CHCH2]2AlH
CAS Number:
Molecular Weight:
142.22
Beilstein:
4123663
MDL number:
UNSPSC 코드:
12352001
PubChem Substance ID:
NACRES:
NA.22

형태

liquid

Quality Level

반응 적합성

reagent type: reductant

농도

1.0 M in hexanes

density

0.701 g/mL at 25 °C

SMILES string

CC(C)C[AlH]CC(C)C

InChI

1S/2C4H9.Al.H/c2*1-4(2)3;;/h2*4H,1H2,2-3H3;;

InChI key

AZWXAPCAJCYGIA-UHFFFAOYSA-N

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일반 설명

Diisobutylaluminum hydride reducing agent is commonly used for the reduction of an ester to aldehyde.

애플리케이션

Diisobutylaluminum hydride solution (1.0 M in hexanes) can be used in the synthesis of potassium diisobutyl-t-butoxyaluminum hydride (PDBBA), a novel reducing agent for the chemoselective conversion of esters in the presence of nitriles. The DIBAL-triethylamine complex can reduce α-oxoketene dithioacetal to the saturated ketone.
Used in Pd-catalyzed reductive debromination of secondary alkyl bromides. O-Debenzylation and ring opening of perbenzylated furanosides. Convenient in situ generation of HZrCp2Cl from ZrCp2Cl2 and DIBAL-H.

신호어

Danger

Hazard Classifications

Aquatic Chronic 2 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Pyr. Liq. 1 - Repr. 2 - Skin Corr. 1B - STOT RE 1 Inhalation - STOT SE 3 - Water-react 1

표적 기관

Central nervous system, Nervous system

보충제 위험성

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 3

Flash Point (°F)

-9.4 °F - closed cup

Flash Point (°C)

-23 °C - closed cup


시험 성적서(COA)

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문서 라이브러리 방문

이미 열람한 고객

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alpha.-Oxoketene dithioacetal chemistry. 2. Conjugate reductions with electrophilic reducing agents.
Gammill R
The Journal of Organic Chemistry, 46(17), 3555-3558 (1981)
Chemoselective Reduction of Esters to Aldehydes by Potassium Diisobutyl-t-butoxyaluminum Hydride (PDBBA).
Chae MJ, et al.
Bull. Korean Chem. Soc., 28(12), 2517-2517 (2007)
Thomas Lecourt et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 10(12), 2960-2971 (2004-06-24)
To explain the remarkable regioselective de-O-benzylating properties of diisobutylaluminium hydride (DIBAL-H) and triisobutylaluminium (TIBAL) towards polybenzylated sugars or cyclodextrins, we propose a plausible mechanistic rationale critically involving the kinetic formation of a product-generating 2:1 Al-benzylated sugar complex. For the reaction
Takashi Tomioka et al.
The Journal of organic chemistry, 76(11), 4669-4674 (2011-04-30)
Stepwise, selective DIBAL reduction of the acetonide diester derived from tartaric acid followed by the Horner-Emmons reaction effectively provided desymmetrized hydroxy mono-olefination products in a one-pot operation.
Carl A Busacca et al.
The Journal of organic chemistry, 73(4), 1524-1531 (2008-01-17)
The reduction of tertiary phosphine oxides (TPOs) and sulfides with diisobutylaluminum hydride (DIBAL-H) has been studied in detail. An extensive solvent screen has revealed that hindered aliphatic ethers, such as MTBE, are optimum for this reaction at ambient temperature. Many

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