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Merck
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214981

Sigma-Aldrich

Diisobutylaluminum hydride solution

1.0 M in THF

동의어(들):

DIBAL, DIBAL-H

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모든 사진(2)

About This Item

Linear Formula:
[(CH3)2CHCH2]2AlH
CAS Number:
1191-15-7
Molecular Weight:
142.22
Beilstein:
4123663
MDL number:
MFCD00008928
UNSPSC 코드:
12352001
eCl@ss:
38120609
PubChem Substance ID:
24852859
NACRES:
NA.22

양식

liquid

Quality Level

200

반응 적합성

reagent type: reductant

농도

1.0 M in THF

bp

65 °C

density

0.866 g/mL at 25 °C

저장 온도

2-8°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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애플리케이션

Diisobutylaluminum hydride solution (1M in THF) is a powerful reducing agent. It can be used in the following reactions:
  • Synthesis of trans-alkene isosteres of protected dipeptides.
  • To generate bis(1,5-cyclooctadiene)nickel(0) (Ni(cod)2) in situ, which can catalyze the conjugate addition of ethenyltributyltin to 2-propenal to form tert-butyldimethyl[((E)-1,4pentadienyl)oxy]silane.
  • Reduction of the arylpropiolate esters to give the corresponding propargyl alcohol.

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.

포장

View returnable container options.

신호어

Danger

유해 및 위험 성명서

H225,H250,H260,H302,H314,H335,H336,H351

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Pyr. Liq. 1 - Skin Corr. 1B - STOT SE 3 - Water-react 1

표적 기관

Central nervous system, Respiratory system

보충제 위험성

EUH014,EUH019

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 1

Flash Point (°F)

1.4 °F - closed cup

Flash Point (°C)

-17 °C - closed cup

개인 보호 장비

Faceshields, Gloves, Goggles

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시험 성적서(COA)

Lot/Batch Number
SHBR2434
SHBR0979
SHBR0978
STBK5189
STBK1428

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문서 라이브러리 방문

A stereocontrolled synthesis of trans-alkene isosteres of dipeptides.
Spaltenstein A, et al.
Tetrahedron Letters, 27(19), 2095-2098 (1986)
D J Kopecky et al.
The Journal of organic chemistry, 65(1), 191-198 (2000-05-18)
An optimized protocol for the DIBALH reductive acetylation of acyclic esters and diesters is described. This reductive acetylation procedure allows a wide variety of esters to be converted into the corresponding alpha-acetoxy ethers in good to excellent yields. It was
Y Kitade et al.
Nucleic acids symposium series, (27)(27), 107-108 (1992-01-01)
Reaction of purine nucleosides, such as 2',3'-isopropylideneinosine (1a) and 2',3'-isopropylideneadenosine (1c), with diisobutylaluminum hydride (DIBAL) in dry tetrahydrofurane resulted in the formation of the corresponding 9-(2',3'-isopropylideneribity)purines (2) in good yields. Oxidation of the ribityl derivatives (2) with NalO4 and subsequent
J Marco-Contelles et al.
Carbohydrate research, 335(1), 63-70 (2001-09-13)
The reaction of DIBALH with bis(heteroannulated)-pyranosides containing the perhydrofuro[2,3-b]pyran moiety is described. The hydride attack at the anomeric carbon (C-9a) resulted in the exclusive tetrahydrofuran ring opening. The selectivity of this reaction has been evaluated as other benzylidene acetals built
Hidetsura Cho et al.
The Journal of organic chemistry, 75(3), 627-636 (2009-12-31)
A systematic investigation of the reductive ring-expansion reaction of cyclic ketoximes fused to aromatic rings with diisobutylaluminum hydride (DIBALH) is described. This reaction regioselectively afforded a variety of five- to eight-membered bicyclic heterocycles or tricyclic heterocycles containing nitrogen neighboring an
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