261971

Sigma-Aldrich

Tricyclohexylphosphine

Synonym(s):
P(Cy)3, PCy3
Linear Formula:
(C6H11)3P
CAS Number:
Molecular Weight:
280.43
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

reaction suitability

reaction type: Cross Couplings
reagent type: ligand
reaction type: Heck Reaction

reagent type: ligand
reaction type: Hiyama Coupling

reagent type: ligand
reaction type: Sonogashira Coupling

reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

mp

81-83 °C (lit.)

functional group

phosphine

SMILES string

C1CCC(CC1)P(C2CCCCC2)C3CCCCC3

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

InChI key

WLPUWLXVBWGYMZ-UHFFFAOYSA-N

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Packaging

1, 5, 25, 250 g in glass bottle

Application

Ligand used in the Pd-catalyzed coupling of malononitrile with aryl halides. Bulky phosphine ligand used with a Pd(0)-triolefinic macrocycle catalyst for Suzuki coupling of aryl bromides and chlorides.
This ligand is applied with Ni as a key intermediate in the formation of cylcopentane compounds.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Sensuke Ogoshi et al.
Journal of the American Chemical Society, 128(16), 5350-5351 (2006-04-20)
Cyclopropyl phenyl ketone underwent oxidative addition to Ni(PCy3) generated from Ni(cod)2 and PCy3 to give a nickeladihydropyran, which is a key intermediate for the Ni(0)-catalyzed homo- or heterocycloaddition to give cyclopentane compounds having two carbonyl substituents at the 1,3-position.
Synlett, 3167-3167 (2006)
Synlett, 3001-3001 (2006)
Adrian Tlahuext-Aca et al.
Dalton transactions (Cambridge, England : 2003), 43(42), 15997-16005 (2014-09-19)
Ni(0)-catalyzed dehydrogenation of benzylic-type imines was performed to yield asymmetrical tetra-substituted imidazoles and 2-imidazolines. This was achieved with a single operational step while maintaining good selectivity and atom economy. The catalytic system shows low to moderate tolerance for fluoro-, trifluoromethyl-...
Sebastijan Kovačič et al.
Macromolecular rapid communications, 36(17), 1605-1611 (2015-07-15)
Metal-organic frameworks (MOFs) nanoparticles in combination with a nonionic surfactant (Pluronic L-121) are used to stabilize dicyclopentadiene (DCPD)-in-water high internal phase emulsions (HIPEs). The resulting HIPEs containing the MIL-100(Fe) nanoparticles (MIL: Materials of Institut Lavoisier) at the interface between the...

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