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Tricyclohexylphosphine tetrafluoroborate

Name: Tricyclohexylphosphine tetrafluoroborate
Brand: ALDRICH

97%

Synonym(s):

Tricyclohexylphosphonium tetrafluoroborate

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About This Item

Linear Formula:

(C₆H₁₁)₃P · HBF₄

CAS Number:

58656-04-5

Molecular Weight:

368.24

MDL number:

MFCD03840580

UNSPSC Code:

12352101

PubChem Substance ID:

24882425

NACRES:

NA.22

Quality Level

100

Assay

97%

form

solid

reaction suitability

reaction type: Arylations
reaction type: Cross Couplings
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Synthesis of C-homoaporphines via microwave-assisted direct arylation.

Chaudhary S and Harding WW.

Tetrahedron, 67(3), 569-575 (2011)

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)

Suzuki-Miyaura cross-coupling of alkenyl tosylates with alkenyl MIDA boronates.

Luthy M and Taylor RJK.

Tetrahedron Letters, 53(27), 3444-3447 (2012)

Articles

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