Tricyclohexylphosphine

Tricyclohexylphosphine
Names
	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
Main hazards	toxic
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	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.

Grubbs' catalyst (first generation)
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.

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[1] Streuli, C. A. (1960). "Determination of Basicity of Substituted Phosphines by Nonaqueous Titrimetry". Anal. Chem. 32: 985–987. doi:10.1021/ac60164a027.

[2] 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.

[3] 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.