Xantphos

Xantphos

Names
IUPAC name 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene
Other names Xantphos
Identifiers
CAS Registry Number	161265-03-8 N
ChemSpider	551930 Y
InChI InChI=1S/C39H32OP2/c1-39(2)33-25-15-27-35(41(29-17-7-3-8-18-29)30-19-9-4-10-20-30)37(33)40-38-34(39)26-16-28-36(38)42(31-21-11-5-12-22-31)32-23-13-6-14-24-32/h3-28H,1-2H3 Y Key: CXNIUSPIQKWYAI-UHFFFAOYSA-N Y InChI=1/C39H32OP2/c1-39(2)33-25-15-27-35(41(29-17-7-3-8-18-29)30-19-9-4-10-20-30)37(33)40-38-34(39)26-16-28-36(38)42(31-21-11-5-12-22-31)32-23-13-6-14-24-32/h3-28H,1-2H3 Key: CXNIUSPIQKWYAI-UHFFFAOYAQ
Jmol-3D images	Image
PubChem	636044
SMILES O6c1c(cccc1P(c2ccccc2)c3ccccc3)C(c7cccc(P(c4ccccc4)c5ccccc5)c67)(C)C
Properties
Chemical formula	C39H32OP2
Molar mass	578.62 g/mol
Appearance	colorless solid
Density	1.34 g/mL
Melting point	224 to 228 °C (435 to 442 °F; 497 to 501 K)
Solubility in water	organic solvents
Hazards
Main hazards	flammable
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
Infobox references

Xantphos is an organophosphorus compound derived from the heterocycle xanthene. It is used as a bidentate ligand and is noteworthy for having a particularly wide bite angle. Such ligands are useful in the hydroformylation of alkenes.^[1] Illustrative of its wide bite angle, it forms both cis and trans adducts of platinum(II) chloride. A related bidentate ligand with a greater bite angle is spanphos.

The ligand is prepared by double directed lithiation of 9,9-dimethylxanthene with sec-butyllithium followed by treatment with chlorodiphenylphosphine.^[2]

References

1. ↑ Piet W. N. M. van Leeuwen, Paul C. J. Kamer, Joost N. H. Reek, and Peter Dierkes (2000). "Ligand Bite Angle Effects in Metal-catalyzed C-C Bond Formation". Chemical Reviews 100 (8): 2741–2769. doi:10.1021/cr9902704. PMID 11749304. 
2. ↑ Mirko Kranenburg, Yuri E. M. van der Burgt, Paul C. J. Kamer, Piet W. N. M. van Leeuwen, Kees Goubitz, and Jan Fraanje (1995). "New Diphosphine Ligands Based on Heterocyclic Aromatics Inducing Very High Regioselectivity in Rhodium-Catalyzed Hydroformylation: Effect of the Bite Angle". Organometallics 14 (6): 3081–3089. doi:10.1021/om00006a057.