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DPEphos

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Chemical compound
DPEphos
DPEphos structure
Names
Preferred IUPAC name bis(diphenylphosphane)
Other names DPEphos, Bis ether
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.203.278 Edit this at Wikidata
EC Number
  • 678-206-0
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C36H28OP2/c1-5-17-29(18-6-1)38(30-19-7-2-8-20-30)35-27-15-13-25-33(35)37-34-26-14-16-28-36(34)39(31-21-9-3-10-22-31)32-23-11-4-12-24-32/h1-28HKey: RYXZOQOZERSHHQ-UHFFFAOYSA-N
SMILES
  • C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3OC4=CC=CC=C4P(C5=CC=CC=C5)C6=CC=CC=C6
Properties
Chemical formula C36H28OP2
Molar mass 538.567 g·mol
Appearance white powder
Melting point 175–176 °C (347–349 °F; 448–449 K)
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H302, H315, H319, H335, H413
Precautionary statements P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Bis ether, also known as DPEphos, is a wide bite angle diphosphine ligand used in inorganic and organometallic chemistry. The name DPEphos is derived from diphenyl ether (DPE) which makes up the ligand's backbone. It is similar to Xantphos, another diphosphine ligand, but is more flexible and has a smaller bite angle (104 vs 108°). It is synthesized from chlorodiphenylphosphine and DPE.

References

  1. Birkholz (née Gensow), Mandy-Nicole; Freixa, Zoraida; van Leeuwen, Piet W. N. M. (2009). "Bite angle effects of diphosphines in C–C and C–X bond forming cross coupling reactions". Chemical Society Reviews. 38 (4): 1099–118. doi:10.1039/B806211K. PMID 19421583.
  2. Kranenburg, Mirko; van der Burgt, Yuri E. M.; Kamer, Paul C. J.; van Leeuwen, Piet W. N. M.; Goubitz, Kees; Fraanje, Jan (June 1995). "New Diphosphine Ligands Based on Heterocyclic Aromatics Inducing Very High Regioselectivity in Rhodium-Catalyzed Hydroformylation: Effect of the Bite Angle" (PDF). Organometallics. 14 (6): 3081–3089. doi:10.1021/om00006a057.
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