192724

Diisobutylaluminum hydride solution

25 wt. % in toluene

• Synonym(s): DIBAL, DIBAL-H
• Linear Formula: [(CH₃)₂CHCH₂]₂AlH
• CAS Number: 1191-15-7
• Molecular Weight: 142.22
• Beilstein: 4123663
• MDL number: MFCD00008928
• UNSPSC Code: 12352001
• PubChem Substance ID: 24851561
• NACRES: NA.22

Properties

• form: liquid
• Quality Level: 200
• reaction suitability: reagent type: reductant
• concentration: 25 wt. % in toluene
• density: 0.846 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

Description

General description

Diisobutylaluminum hydride solution is a strong reducing agent used to convert arylpropiolate esters to their propargyl alcohols.[1]

Diisobutylaluminum hydride reducing agent is commonly used for the reduction of an ester to aldehyde.[2]

Application

Diisobutylaluminum hydride solution (25 wt. % in toluene) has been used for the reduction of imides:[3]

• N

• -(cis-2-Vinylcyclohexyl)succinimide to 1-(cis-2-vinylcyclohexyl)-5-hydroxy-2-pyrrolidinone
• N-(But-4-en-1-y1)-2(E)-(carbethoxymethylidene)-5-oxo-pyrrolidine to N-(but-4-en-1-yl)- 2(E)-(carbethoxymethylidene)-5-hydroxypyrrolidine
• N-(Hept-1-en-4-y1)-2(E)-(carbethoxymethylidene)-5-oxo-pyrrolidine to N-(hept-1-en-4-y1)-2(E)-(carbethoxymethylidene)-5-hydroxypyrrolidine
• N-(cis-2-Vinylcyclohexyl)-2-(carbethoxymethylidene)-5-oxopyrrolidine to rel-(3aR,SS,5aS,SaR)-1( E)-(carbethoxymethylidene)-5-(formyloxy)dodecahydropyrrolo[1,2-a]quinoline

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.

Packaging

The 25 g Sure/Seal^™ bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.

View returnable container options.

Legal Information

Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

Safety Information

• Pictograms: GHS02,GHS08,GHS05,GHS07
• Signal Word: Danger
• Hazard Statements: H225,H250,H260,H304,H314,H336,H361d,H373,H412
• Precautionary Statements: P210 - P231 + P232 - P280 - P301 + P330 + P331 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P370 + P378
• Hazard Classifications: Aquatic Chronic 3 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Pyr. Liq. 1 - Repr. 2 - Skin Corr. 1B - STOT RE 2 Inhalation - STOT SE 3 - Water-react 1
• Target Organs: Central nervous system
• Supplementary Hazards: EUH014
• Storage Class Code: 4.2 - Pyrophoric and self-heating hazardous materials
• WGK: WGK 3
• Flash Point(F): 39.2 °F - closed cup
• Flash Point(C): 4 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves