214965

Diisobutylaluminum hydride solution

1.0 M in heptane

• 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: 24852857
• NACRES: NA.22

Properties

• form: liquid
• Quality Level: 200
• reaction suitability: reagent type: reductant
• concentration: 1.0 M in heptane
• density: 0.731 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

Application

Diisobutylaluminum hydride (DIBAL-H) is a common reducing agent to reduce aldehydes, ketones, esters, acids and acid chlorides to the corresponding alcohols.[1] Some of the applications are:

• Synthesis of α-acetoxy ethers by reduction and subsequent acetylation of esters.[2]
• Synthesis of coniferyl, sinapyl, and p-coumaryl alcohol by selective reduction of corresponding cinnamate esters.[3]
• Reduction of secondary phosphine oxides (SPOs) to the corresponding phosphines.[4]
• DIBAL-H can also be used in the hydroalumination of alkene and alkynes.[5]

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,GHS09
• signalword: Danger
• hcodes: H225,H250,H260,H304,H314,H336,H410
• pcodes: P210 - P231 + P232 - P280 - P301 + P330 + P331 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 - P370 + P378
• Hazard Classifications: Aquatic Acute 1 - Aquatic Chronic 1 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - 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_germany: WGK 2
• flash_point_f: 30.2 °F
• flash_point_c: -1 °C