214973

Diisobutylaluminum hydride solution

1.0 M in methylene chloride

• Synonym(s): DIBAL, DIBAL-H
• Linear Formula: [(CH₃)₂CHCH₂]₂AlH
• CAS Number: 1191-15-7
• Molecular Weight: 142.22
• NACRES: NA.22
• PubChem Substance ID: 24852858
• eCl@ss: 38120609
• UNSPSC Code: 12352001
• MDL number: MFCD00008928
• Beilstein/REAXYS Number: 4123663
• Form: liquid

Properties

• InChI: 1S/2C4H9.Al.H/c2*1-4(2)3;;/h2*4H,1H2,2-3H3;;
• SMILES string: CC(C)C[AlH]CC(C)C
• InChI key: AZWXAPCAJCYGIA-UHFFFAOYSA-N
• form: liquid
• reaction suitability: reagent type: reductant
• concentration: 1.0 M in methylene chloride
• density: 1.23 g/mL at 25 °C
• storage temp.: 2-8°C
• Quality Level: 200

Description

General description

Diisobutylaluminum hydride is a reducing agent for many functional groups commonly used in organic synthesis.[1][2]

Application

Diisobutylaluminum hydride solution (1 M in dichloromethane) has been used in the conversion of esters into α-fluoro-α,β-unsaturated esters in the presence of fluorocarboalkoxy-substituted dialkyl phosphonate anions via Horner-Wadsworth-Emmons reaction.[3] It can be used in the multi-step synthesis of (S)-2-methyl tetrahydropyridine-N-oxide, a key structural moiety of bio-active compounds like himbacine and solenopsin-A.[4]

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.

Safety Information

• pictograms: GHS02,GHS08,GHS05,GHS07
• signalword: Danger
• hcodes: H250,H260,H314,H336,H351
• pcodes: P231 + P232 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P370 + P378
• Hazard Classifications: Carc. 2 - Eye Dam. 1 - Pyr. Liq. 1 - Skin Corr. 1B - 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: WGK 2