Tricyclohexylphosphonium tetrafluoroborate, 99%

Name: Tricyclohexylphosphonium tetrafluoroborate, 99%
SKU: H27428.06

CAS: 58656-04-5 | C18H34BF4P | 368.25 g/mol

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Catalog number H27428.06

also known as H27428-06

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Chemical Identifiers

CAS58656-04-5

IUPAC Nametetrafluoroboranuide; tricyclohexylphosphanium

Molecular FormulaC18H34BF4P

InChI KeyMYSMMEUXKHJYKH-UHFFFAOYSA-O

SMILESF[B-](F)(F)F.C1CCC(CC1)[PH+](C1CCCCC1)C1CCCCC1

Specifications

Specification Sheet

Phosphorus-31 NMRConforms to structure

FormCrystalline powder or powder

Assay (Aqueous acid-base Titration)>98.5 to <101.5%

Proton NMRConforms to structure

Appearance (Color)White

Tricyclohexylphosphonium tetrafluoroborate is used with ruthenium (1,5-cyclooctadiene)ruthenium dimer to catalyze the dehydrogenative coupling of alcohols and amines to form amide bonds. It is also used in suzuki reaction.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
Tricyclohexylphosphonium tetrafluoroborate is used with ruthenium (1,5-cyclooctadiene)ruthenium dimer to catalyze the dehydrogenative coupling of alcohols and amines to form amide bonds. It is also used in suzuki reaction.

Solubility
Soluble in water.

Notes
Incompatible with strong oxidizing agents.

RUO – Research Use Only

General References:

Air-stable replacement for tricyclohexylphosphine in various Pd-catalyzed coupling reactions. Used in conjunction with Bis(1,5-cyclooctadiene) nickel(0), 39234 in Ni(0)-catalyzed Suzuki-Miyaura-type coupling of alkenyl phosphates with arylboronic acids and esters to give 1,1-diarylalkenes: Chem. Commun., 4137 (2006). See also Tri-tert-butyl phosphonium tetrafluoroborate, L19752.
Hayashi, S.; Kojima, Y.; Koizumi, T. Highly regioselective Pd/C-catalyzed direct arylation toward thiophene-based π-conjugated polymers. Polym. Chem. 2015, 6 (6), 881-885.
Ueda, Y.; Tsuji, H.; Tanaka, H.; Nakamura, E. Synthesis, Crystal Packing, and Ambipolar Carrier Transport Property of Twisted Dibenzo [g, p] chrysenes. Chem. Asian J. 2014, 9 (6), 1623-1628.