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261971

Tricyclohexylphosphine

Name: Tricyclohexylphosphine
Brand: ALDRICH

Synonym(s):

PCy₃, P(Cy)₃

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About This Item

Linear Formula:

(C₆H₁₁)₃P

CAS Number:

2622-14-2

Molecular Weight:

280.43

EC Number:

220-069-2

MDL number:

MFCD00003853

UNSPSC Code:

12350000

PubChem Substance ID:

24855848

NACRES:

NA.22

form

solid

Quality Level

100

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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Related Categories

Phosphine Ligands

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

GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Precautionary Statements

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Formation of nickeladihydropyran by oxidative addition of cyclopropyl ketone. Key intermediate in nickel-catalyzed cycloaddition.

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)

Synthesis of tetra-substituted imidazoles and 2-imidazolines by Ni(0)-catalyzed dehydrogenation of benzylic-type imines.

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-

Synthesis and Catalytic Performance of Hierarchically Porous MIL-100(Fe)@polyHIPE Hybrid Membranes.

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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