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214973 Sigma-Aldrich

Diisobutylaluminum hydride solution

1.0 M in methylene chloride

Synonym: DIBAL-H, DIBAL

  • CAS Number 1191-15-7

  • Linear Formula [(CH3)2CHCH2]2AlH

  • Molecular Weight 142.22

  •  Beilstein/REAXYS Number 4123663

  •  MDL number MFCD00008928

  •  eCl@ss 38120609

  •  PubChem Substance ID 24852858

  •  NACRES NA.22

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Properties

Related Categories Aluminum Hydrides, Chemical Synthesis, Reduction, Synthetic Reagents
Quality Level   200
concentration   1.0 M in methylene chloride
density   1.23 g/mL at 25 °C
storage temp.   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

Description

General description

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

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. 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.

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

1 L in Sure/Seal™

100, 800 mL in Sure/Seal™

Safety & Documentation

Safety Information

Signal word 
Danger
Hazard statements 
Target organs 
Central nervous system
Supplemental Hazard Statements 
EUH014
RIDADR 
UN 3394 4.3(4.2) / PGI
WGK Germany 
WGK 2

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

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Peer-Reviewed Papers
15

References

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