Tricyclohexylphosphine

Tricyclohexylphosphine

Names
IUPAC name Tricyclohexylphosphane
Other names P(Cy)3 PCy3
Identifiers
CAS Number	2622-14-2
ChemSpider	68315
Jmol interactive 3D	Image Image
PubChem	75806
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.

References

1. C. A. Streuli, "Determination of Basicity of Substituted Phosphines by Nonaqueous Titrimetry", Analytical Chemistry 1960, volume 32, pages 985-987.doi:10.1021/ac60164a027
2. R. C. Bush and R. J. Angelici (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". Inorganica Chimica Acta 25: L41–42. doi:10.1016/S0020-1693(00)95635-4.

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  Grubbs catalyst (1st generation)

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  Crabtree's catalyst