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Tricyclohexylphosphine information


Tricyclohexylphosphine
Names
Preferred IUPAC name
Tricyclohexylphosphane
Other names
P(Cy)3
PCy3
Identifiers
CAS Number
  • 2622-14-2 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
ChemSpider
  • 68315 ☒N
ECHA InfoCard 100.018.246 Edit this at Wikidata
PubChem CID
  • 75806
UNII
  • 34HJS55VCG checkY
CompTox Dashboard (EPA)
  • DTXSID9062562 Edit this at Wikidata
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 ☒N
    Key: WLPUWLXVBWGYMZ-UHFFFAOYSA-N ☒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).
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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 (pKa = 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.

  1. ^ Streuli, C. A. (1960). "Determination of Basicity of Substituted Phosphines by Nonaqueous Titrimetry". Anal. Chem. 32 (8): 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.

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Tricyclohexylphosphine

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Tricyclohexylphosphine is the tertiary phosphine with the formula P(C6H11)3. Commonly used as a ligand in organometallic chemistry, it is often abbreviated...

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Steric effects

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4-di-tert-butylphenyl)phosphite, a widely used stabilizer in polymers. Tricyclohexylphosphine, a bulky phosphine ligand used in homogeneous catalysis and, with...

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Grubbs catalyst

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catalyst. It is synthesized from RuCl2(PPh3)3, phenyldiazomethane, and tricyclohexylphosphine in a one-pot synthesis. The first-generation Grubbs catalyst was...

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Cyclooctadiene iridium chloride dimer

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5-Cyclooctadiene)(Pyridine)-(Tricyclohexylphosphine)Iridium(I)Hexafluorophosphate". [η4-1,5-Cyclooctadiene)(Pyridine)(Tricyclohexylphosphine)Iridium(I)Hexafluorophosphate...

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Ligand

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macrocyclic ligand see also the N,N′,N″-trimethylated analogue Tricyclohexylphosphine P(C6H11)3 or PCy3 neutral monodentate Triethylenetetramine (trien)...

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Frustrated Lewis pair

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example, many FLPs split hydrogen molecules. Thus, a mixture of tricyclohexylphosphine (PCy3) and tris(pentafluorophenyl)borane reacts with hydrogen to...

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Triisopropylphosphine

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cone angle of 160. Pi-Pr3 is similar to the more frequently used tricyclohexylphosphine. The triisopropyl derivative however, is a liquid at room temperature...

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Boronic acid

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in this reaction is tris(dibenzylideneacetone)dipalladium(0) / tricyclohexylphosphine. Another conjugate addition is that of gramine with phenylboronic...

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Olefin metathesis

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metathesis catalyst, (PPh3)2Cl2Ru=CHCH=CPh2: The corresponding tricyclohexylphosphine complex (PCy3)2Cl2Ru=CHCH=CPh2 was also shown to be active. This...

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Tributylphosphine

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aldehydes to branched-chain aldehydes in the product mixture. However, tricyclohexylphosphine is even more effective for this purpose (although more expensive)...

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Phosphine telluride

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like trioctylphoshine telluride, tributylphosphine telluride and tricyclohexylphosphine telluride are reagents used in the preparation of metal telluride...

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Metal carbido complex

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crystallographically and are distinguishable by their Cs symmetry. Addition of tricyclohexylphosphine to the carbene complex (PPh3)2(Cl)2Ru=C(CHCO2Me)2 results in olefin...

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Indium trihydride

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below −30 °C or in dilute solution. The 1:1 and 1:2 complexes with tricyclohexylphosphine (PCy3) have been characterised crystallographically. The average...

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Zhan catalyst

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Dichloro((5-((dimethylamino)sulfonyl)-2-(1-methylethoxy-O)phenyl)methylene-C)(tricyclohexylphosphine)ruthenium(IV) Identifiers CAS Number 918871-44-0 3D model (JSmol)...

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Organonickel chemistry

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with two equivalents of diphenylacetylene with NiCOD2 and tricyclohexylphosphine first to nickelapyrroline and with a second insertion a nickeldihydroazepine...

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Organoruthenium chemistry

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While monodentate phosphine ligands such as triphenylphosphine and tricyclohexylphosphine are most common, bidentate phosphine ligands can also be useful...

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Metal carbon dioxide complex

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1992). "A bonding-reactivity relationship for (carbon dioxide)bis(tricyclohexylphosphine)nickel: a comparative solid-state-solution nuclear magnetic resonance...

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