Tricyclohexylphosphine

Tricyclohexylphosphine
IUPAC name tricyclohexylphosphane
Other names tricyclohexylphosphine P(Cy)3 PCy3
Identifiers
CAS number	2622-14-2
Jmol-3D images	Image 1
SMILES C1(CCCCC1)P(C2CCCCC2)C3CCCCC3
InChI InChI=1/C18H33P/c1/h16-18H,1-15H2
Properties
Molecular formula	C18H33P
Molar mass	280.43 g mol−1
Melting point	82 °C
Hazards
Main hazards	toxic
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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) and a large ligand cone angle.^[1]

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

References

1. ^ 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. 

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  Grubbs catalyst (1st generation)

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  Crabtree's catalyst