631493

Tricyclohexylphosphine tetrafluoroborate

97%

• Synonym(s): Tricyclohexylphosphonium tetrafluoroborate
• 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

Properties

• 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

Description

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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)