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192724 Sigma-Aldrich

Diisobutylaluminum hydride solution

25 wt. % in toluene

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

  •  PubChem Substance ID 24851561

  •  NACRES NA.22

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Properties

Related Categories 25mL Sure/Seal Reagents, Aluminum Hydrides, Chemical Synthesis, Organometallic Reagents, Reduction,
Quality Level   200
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 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

4×25, 100, 700 g in Sure/Seal™

7, 15 kg in Kilo-Lab™

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

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Legal Information

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

Safety & Documentation

Safety Information

Signal word 
Danger
Target organs 
Central nervous system
Supplemental Hazard Statements 
EUH014
RIDADR 
UN 3394 4.3(4.2) / PGI
WGK Germany 
WGK 2
Flash Point(F) 
39.2 °F - closed cup
Flash Point(C) 
4 °C - closed cup

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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