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/REAXYS Number: 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.

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

Application

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

• 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
• signalword: Danger
• hcodes: H225,H250,H260,H304,H314,H336,H361d,H373,H412
• pcodes: 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
• supp_hazards: EUH014
• Storage Class: 4.2 - Pyrophoric and self-heating hazardous materials
• wgk_germany: WGK 3
• flash_point_f: 39.2 °F - closed cup
• flash_point_c: 4 °C - closed cup
• ppe: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter