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631493

Sigma-Aldrich

Tricyclohexylphosphine tetrafluoroborate

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.

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PDSCL

Deleterious substance

PRTR

Class I Designated Chemical Substances

JAN Code

631493-1G:4548173174358
631493-VAR:
631493-5G:4548173174365
631493-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
SHBJ3762
23796EMV
23796EM
15107CJ
14219BJ

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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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