Xantphos

Not to be confused with XPhos.

Xantphos is an organophosphorus compound derived from the heterocycle xanthene. It is used as a bidentate diphosphine ligand and is noteworthy for having a particularly wide bite angle (108°).^[1] Such ligands are useful in the hydroformylation of alkenes.^[2] Illustrative of its wide bite angle, it forms both cis and trans adducts of platinum(II) chloride. In the latter context, xantphos is classified as a trans-spanning ligand. A related bidentate ligand with a greater bite angle is spanphos.

Xantphos

Ph stands for phenyl
Names
Preferred IUPAC name (9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane)
Other names Xantphos
Identifiers
CAS Number	161265-03-8 Y
3D model (JSmol)	Interactive image
ChemSpider	551930 Y
ECHA InfoCard	100.118.008
PubChem CID	636044
UNII	NMU72MOG9B Y
CompTox Dashboard (EPA)	DTXSID20348350
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
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
Occupational safety and health (OHS/OSH):
Main hazards	flammable
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

The ligand is prepared by double directed lithiation of 9,9-dimethylxanthene with sec-butyllithium followed by treatment with chlorodiphenylphosphine.^[3]