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668494 Sigma-Aldrich

(−)-1,2-Bis[(2R,5R)-2,5-diethylphospholano]benzene

kanata purity

Synonym: (2R,2′R,5R,5′R)-2,2′-5,5′-Tetraethyl-1,1′-(o-phenylene)diphospholane, (R,R)-Ethyl-DUPHOS

  • CAS Number 136705-64-1

  • Empirical Formula (Hill Notation) C22H36P2

  • Molecular Weight 362.47

  •  Beilstein/REAXYS Number 4814174

  •  MDL number MFCD00142335

  •  PubChem Substance ID 24884987

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, DuPhos/BPE, Privileged Ligands and Complexes More...
Quality Level   100
refractive index   n20/D 1.6
density   1.01 g/mL at 25 °C
SMILES string   CC[C@@H]1CC[C@@H](CC)P1c2ccccc2P3[C@H](CC)CC[C@H]3CC
InChI   1S/C22H36P2/c1-5-17-13-14-18(6-2)23(17)21-11-9-10-12-22(21)24-19(7-3)15-16-20(24)8-4/h9-12,17-20H,5-8,13-16H2,1-4H3/t17-,18-,19-,20-/m1/s1
InChI key   GVVCHDNSTMEUCS-UAFMIMERSA-N

Description

Application

(−)-1,2-Bis[(2R,5R)-2,5-diethylphospholano]benzene is a chiral ligand that can be used to prepare the Duphos-Rhodium metal complex, which is used as a catalyst in asymmetric hydrogenation reactions.

DuPhos and BPE Ligands: Highly Efficient Privileged Ligands

Packaging

100 mg in clear glass bottle

500 mg in amber glass bottle

Legal Information

Sold in collaboration with Kanata Chemical Technologies Inc. for research purposes only. These compounds were made and sold under license from E.I. du Pont de Nemours and Company, which license does not include the right to use the compounds in producing products for sale in the pharmaceutical field.

Safety & Documentation

Safety Information

Hazard statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles

Articles

DuPhos and BPE Phospholane Ligands and Complexes

In the early 1990s, Burk and coworkers developed new electron-rich C2 symmetric bis(phospholane) ligands. The modular nature of these ligands allowed for variation of both phosphane substituent and b...
William Sommer and Daniel Weibel
ChemFiles 2008, 8.2, 34.
Keywords: Aminations, Asymmetric catalysis, Asymmetric synthesis, Building blocks, Catalysis, Crotylborations, Hydrogenations, Ligands, Reductions, Reductive aminations

Related Content

DuPhos and BPE Ligands: Highly Efficient Privileged Ligands

Introduction Asymmetric hydrogenation reactions represent the ideal process for the commercial manufacture of single-enantiomer compounds, because of the ease by which these robust procedures can be ...
Keywords: Addition reactions, Alkylations, Amidations, Aminations, Asymmetric synthesis, Building blocks, Catalysis, Cycloadditions, Electronics, Hydrogenations, Ligands, Pharmaceutical, Purification, Reductions, Reductive aminations, transformation

Peer-Reviewed Papers
15

References

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