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592285

Sigma-Aldrich

Tricyclohexylphosphine solution

1 M in toluene

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Synonym(s):
NSC 158657, PCy3
Linear Formula:
(C6H11)3P
CAS Number:
2622-14-2
Molecular Weight:
280.43
Beilstein:
957171
MDL number:
MFCD00003853
UNSPSC Code:
12350000
PubChem Substance ID:
24881380
NACRES:
NA.22

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: ligand
reaction type: Cross Couplings

concentration

1 M in toluene

density

0.901 g/mL at 25 °C

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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Application

Catalyst for:
  • Carbonylative Suzuki-coupling of benzyl halides with potassium aryltrifluoroborates
  • Suzuki-Miyaura reactions of aryl sulfonates / halides with arylboronic acids
  • Synthesis of an acromelic acid A analog based 11C-labeled PET tracer
  • Synthesis of (-)-Exiguolide and its analogues
  • Allylation of zinc enolates

Signal Word

Danger

Hazard Classifications

Aquatic Chronic 3 - Asp. Tox. 1 - Eye Irrit. 2 - Flam. Liq. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 2 - STOT SE 3

Target Organs

Central nervous system, Respiratory system

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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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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