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678635 Sigma-Aldrich

1,2-Bis[(2R,5R)-2,5-dimethylphospholano]benzene monooxide

kanata purity

Synonym: (2R,5R)-1-{2-[(2R,5R)-2,5-Dimethylphospholan-1-yl]phenyl}-2,5-dimethylphospholane 1-oxide, R,R-Me-BozPhos

  • CAS Number 638132-66-8

  • Empirical Formula (Hill Notation) C18H28OP2

  • Molecular Weight 322.36

  •  MDL number MFCD09750450

  •  PubChem Substance ID 24885440

  •  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
optical activity   [α]22/D -171°, c = 1 in chloroform
mp   116-122 °C
SMILES string   C[C@@H]1CC[C@@H](C)P1(C2=CC=CC=C2P3[C@H](C)CC[C@H]3C)=O
InChI   1S/C18H28OP2/c1-13-9-10-14(2)20(13)17-7-5-6-8-18(17)21(19)15(3)11-12-16(21)4/h5-8,13-16H,9-12H2,1-4H3/t13-,14-,15-,16-/m1/s1
InChI key   ORZVYNTUPREFTI-KLHDSHLOSA-N

Description

General description

1,2-Bis[(2R,5R)-2,5-dimethylphospholano]benzene monooxide is a chiral ligand whose copper complexes are used extensively in many organic reactions such as addition to imines, nitroalkenes, and reduction of β,β-disubstituted vinyl sulfones.

Application

1,2-Bis[(2R,5R)-2,5-dimethylphospholano]benzene monoxide can be used:
• As a ligand in the preparation of dihydroquinolones and dihydroisoquinolones through palladium-catalyzed C-H functionalization of cyclopropane derivatives.
• As an organocatalyst in the [4+1] annulation reactions of 2-enoylpyridine pyridine N-oxides and olefins with Morita-Baylis-Hillman (MBH) carbonates to yield dihydrofurans derivatives enantioselectively.
• As a ligand in the copper-catalyzed synthesis of chiral nitroalkanes via the addition of dialkylzinc to β-nitroalkenes.

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

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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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

Peer-Reviewed Papers
15

References

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