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686344 Sigma-Aldrich

4,4,5,5-Tetramethyl-1,3,2-dioxaphospholane 2-oxide

95%

Synonym: 2-Oxo-4,4,5,5-tetramethyl-1,3,2-dioxaphospholane, 4,4,5,5-Tetramethyl-1,3,2-dioxaphospholan-2-ol, HASPO-1, Phosphonic acid pinacol ester, Pinacol phosphonate

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Properties

Related Categories Catalysis and Inorganic Chemistry, Chemical Synthesis, Phosphine Compounds, Phosphine Ligands
assay   95%
mp   99-106 °C
functional group   phosphine
reaction suitability   reaction type: Buchwald-Hartwig Cross Coupling Reaction
  reaction type: Heck Reaction
  reaction type: Hiyama Coupling
  reaction type: Negishi Coupling
  reaction type: Sonogashira Coupling
  reaction type: Stille Coupling
  reaction type: Suzuki-Miyaura Coupling
  reagent type: ligand
SMILES string   CC1(C)O[PH](=O)OC1(C)C
InChI   1S/C6H13O3P/c1-5(2)6(3,4)9-10(7)8-5/h10H,1-4H3
InChI key   QPONEGYFSLRCLJ-UHFFFAOYSA-N

Description

Application

• Preligand in palladium-catalyzed Kumada cross-coupling reactions of aryl tosylates with Grignard reagents
• Catalyst for reversible chain transfer polymerizations

Reactant for:
• Synthesis of oxapalladacycle as catalyst for Markovnikov-type addition
• Preparation of palladium(II) complexes as catalysts for Heck cross-coupling reactions
• Preparation of palladium catalysts for asymmetric hydrogenation of a-keto phosphonates
• Hydrophosphorylation of alkenes, dienes and enynes in the presence of rhodium catalysts

Air-stable preligand for Pd-catalyzed Kumada-type cross-couplings.

Packaging

1 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
3

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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