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  • 682869 - (11bS,11′bS)-4,4′-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis-dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin

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682869 Sigma-Aldrich

(11bS,11′bS)-4,4′-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis-dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin

Synonym: S,S-Reetz X-Diphosphonite

  • CAS Number 349114-57-4

  • Empirical Formula (Hill Notation) C55H36O5P2

  • Molecular Weight 838.82

  •  MDL number MFCD09842740

  •  PubChem Substance ID 329760513

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Hydrogenation, Privileged Ligands and Complexes,
Quality Level   100
optical activity   [α]22/D -245°, c = 1 in chloroform
mp   195-207 °C (dec.)
SMILES string   CC1(C)c2cccc(P3Oc4ccc5ccccc5c4-c6c(O3)ccc7ccccc67)c2Oc8c(cccc18)P9Oc%10ccc%11ccccc%11c%10-c%12c(O9)ccc%13ccccc%12%13
InChI   1S/C55H36O5P2/c1-55(2)41-21-11-23-47(61-57-43-29-25-33-13-3-7-17-37(33)49(43)50-38-18-8-4-14-34(38)26-30-44(50)58-61)53(41)56-54-42(55)22-12-24-48(54)62-59-45-31-27-35-15-5-9-19-39(35)51(45)52-40-20-10-6-16-36(40)28-32-46(52)60-62/h3-32H,1-2H3
InChI key   DXZANFKSPAISOB-UHFFFAOYSA-N

Description

Application

• Catalyst for asymmetric hydrogenation of quinolines catalyzed by iridium complexes of BINOL-derived diphosphonites
• Ligand in asymmetric Ni-catalyzed hydrocyanation of styrene and other vinylarenes

This diphosphonite ligand has been successfully employed in Noyori-type asymmetric transfer hydrogenation of prochiral ketones.

Packaging

100, 500 mg in amber glass bottle

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

Reetz Ligands

In 1998, Reetz et al. reported the synthesis of a new generation of ligand for enantioselective, catalyzed hydrogenation. Based on BINOL-derived diphosphonite molecules, these ligands showed good ena...
William Sommer and Daniel Weibel
Aldrich ChemFiles 2008, 8.2, 54.
Keywords: Addition reactions, Asymmetric synthesis, Catalysis, Chemfiles, Hydrogenations, Ligands

Peer-Reviewed Papers
15

References

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