Tricyclohexylphosphine

Tricyclohexylphosphine
Names
	Preferred IUPAC name Tricyclohexylphosphane
	Other names P(Cy)3; PCy3
Identifiers
CAS Number	2622-14-2 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	68315 ;
ECHA InfoCard	100.018.246
PubChem CID	75806;
CompTox Dashboard (EPA)	DTXSID9062562 ;
	InChI InChI=1S/C18H33P/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h16-18H,1-15H2 Key: WLPUWLXVBWGYMZ-UHFFFAOYSA-N ; InChI=1/C18H33P/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h16-18H,1-15H2 Key: WLPUWLXVBWGYMZ-UHFFFAOYAM;
	SMILES C1(CCCCC1)P(C2CCCCC2)C3CCCCC3; C1CCC(CC1)P(C2CCCCC2)C3CCCCC3;
Properties
Chemical formula	C18H33P
Molar mass	280.43 g mol−1
Appearance	white solid
Melting point	82 °C (180 °F; 355 K)
Solubility in water	organic solvents
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	toxic
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Tricyclohexylphosphine is the tertiary phosphine with the formula P(C₆H₁₁)₃. Commonly used as a ligand in organometallic chemistry, it is often abbreviated to PCy₃, where Cy stands for cyclohexyl. It is characterized by both high basicity (pK_a = 9.7)^[1] and a large ligand cone angle (170°).^[2]^[3]

Important complexes containing P(Cy)₃ ligands include the 2005 Nobel Prize-winning Grubbs' catalyst and the homogeneous hydrogenation catalyst Crabtree's catalyst.

References

^ Streuli, C. A. (1960). "Determination of Basicity of Substituted Phosphines by Nonaqueous Titrimetry". Anal. Chem. 32: 985–987. doi:10.1021/ac60164a027.
^ Bush, R. C.; Angelici, R. J. (1988). "Phosphine basicities as determined by enthalpies of protonation". Inorg. Chem. 27 (4): 681–686. doi:10.1021/ic00277a022.
^ Immirzi, A.; Musco, A. (1977). "A Method to Measure the Size of Phosphorus Ligands in Coordination Complexes". Inorg. Chim. Acta. 25: L41–42. doi:10.1016/S0020-1693(00)95635-4.