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631493

Tricyclohexylphosphine tetrafluoroborate

97%, solid

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
UNSPSC Code:
12352101
PubChem Substance ID:
24882425
NACRES:
NA.22
MDL number:
MFCD03840580
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Product Name

Tricyclohexylphosphine tetrafluoroborate, 97%

Quality Segment

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.

Storage Class

11 - Combustible Solids

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

PPE (personal protective equipment)

Eyeshields, Gloves, type N95 (US)

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