tricyclohexylphosphine
{{chembox
|Verifiedfields = changed
|Watchedfields = changed
|verifiedrevid = 424994779
|ImageFile = Tricyclohexylphosphine-2D-skeletal.png
|ImageFile1 = Tricyclohexylphosphine-from-xtal-1991-3D-balls.png
|ImageFile2 = Tricyclohexylphosphine-from-xtal-1991-3D-vdW.png
|PIN = Tricyclohexylphosphane
|OtherNames = P(Cy)3
PCy3
|Section1={{Chembox Identifiers
|CASNo_Ref = {{cascite|correct|CAS}}
|CASNo = 2622-14-2
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 34HJS55VCG
|SMILES = C1(CCCCC1)P(C2CCCCC2)C3CCCCC3
|PubChem = 75806
|ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
|ChemSpiderID = 68315
|SMILES2 = C1CCC(CC1)P(C2CCCCC2)C3CCCCC3
|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
|InChIKey = WLPUWLXVBWGYMZ-UHFFFAOYAM
|StdInChI_Ref = {{stdinchicite|changed|chemspider}}
|StdInChI = 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
|StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
|StdInChIKey = WLPUWLXVBWGYMZ-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
|Formula = C18H33P
|MolarMass = 280.43 g mol−1
|Appearance = white solid
|MeltingPtC = 82
|Solubility = organic solvents
}}
|Section3={{Chembox Hazards
|MainHazards = toxic
}}
}}
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 (pKa = 9.7){{cite journal|first=C. A.|last=Streuli|title=Determination of Basicity of Substituted Phosphines by Nonaqueous Titrimetry|journal=Anal. Chem.|date=1960|volume=32|issue=8 |pages=985–987|doi=10.1021/ac60164a027}} and a large ligand cone angle (170°).{{cite journal | first1 = R. C. | last1 = Bush | first2 = R. J. | last2 = Angelici | title = Phosphine basicities as determined by enthalpies of protonation | year = 1988 | journal = Inorg. Chem. | volume = 27 | issue = 4 | pages = 681–686 | doi = 10.1021/ic00277a022}}{{cite journal | last1 = Immirzi | first1 = A. | last2 = Musco | first2 = A. | title = A Method to Measure the Size of Phosphorus Ligands in Coordination Complexes | doi = 10.1016/S0020-1693(00)95635-4 | year = 1977 | journal = Inorg. Chim. Acta | volume = 25 | pages = L41–42}}
Important complexes containing P(Cy)3 ligands include the 2005 Nobel Prize-winning Grubbs' catalyst and the homogeneous hydrogenation catalyst Crabtree's catalyst.
Image:Grubbs_Catalyst_1st_Generation.svg|Grubbs' catalyst (first generation)
Image:Crabtree.png|Crabtree's catalyst