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631493

Sigma-Aldrich

Tricyclohexylphosphine tetrafluoroborate

97%

Linear Formula:
(C6H11)3P · HBF4
CAS Number:
Molecular Weight:
368.24
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

reaction suitability

reaction type: Cross Couplings
reagent type: ligand
reaction type: Arylations

reagent type: ligand
reaction type: Sonogashira Coupling

reagent type: ligand
reaction type: Stille Coupling

reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

mp

164 °C (lit.)

functional group

phosphine

SMILES string

F[B-](F)(F)F.[H][P+](C1CCCCC1)(C2CCCCC2)C3CCCCC3

InChI

1S/C18H33P.BF4/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;2-1(3,4)5/h16-18H,1-15H2;/q;-1/p+1

InChI key

MYSMMEUXKHJYKH-UHFFFAOYSA-O

General description

Tricyclohexylphosphine tetrafluoroborate (PCy3·HBF4) is an inexpensive and air-stable phosphine ligand, commonly used in cross-coupling reactions.

Application

Tricyclohexylphosphine tetrafluoroborate may be used in the following processes:
  • As a ligand for preparing C-homoaporphine alkaloids via microwave-assisted direct-arylation.
  • To synthesize poly-[9,9-bis(3-propylamide-2-methylpropyl sulfonic acid) fluorene]-co-(4,4′-diphenyl) (PFDBSO3H), which can be employed as a template and doping agent for enhancing the conductivity of poly(3,4-ethylenedioxythiophene) (PEDOT) films.
  • To improve the reactivity of palladium-catalyzed Suzuki-Miyaura cross-coupling reaction between MIDA boronates and less activated alkenyl tosylates.
Used with Ru(cod)Cl dimer to catalyze the dehydrogenative coupling of alcohols and amines to form amide bonds.

Packaging

1, 5 g in glass bottle

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Certificate of Origin

Synthesis and characterization of PEDOT aqueous dispersions with sulfonated polyfluorene as a template and doping agent.
Gu J, et al.
Reactive functional Polymers, 100, 83-88 (2016)
Synthesis of C-homoaporphines via microwave-assisted direct arylation.
Chaudhary S and Harding WW.
Tetrahedron, 67(3), 569-575 (2011)
Suzuki-Miyaura cross-coupling of alkenyl tosylates with alkenyl MIDA boronates.
Luthy M and Taylor RJK.
Tetrahedron Letters, 53(27), 3444-3447 (2012)

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