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631493

Sigma-Aldrich

Tricyclohexylphosphine tetrafluoroborate

97%

Synonyme(s) :

Tricyclohexylphosphonium tetrafluoroborate

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5 G
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About This Item

Formule linéaire :
(C6H11)3P · HBF4
Numéro CAS:
58656-04-5
Poids moléculaire :
368.24
Numéro MDL:
MFCD03840580
Code UNSPSC :
12352101
ID de substance PubChem :
24882425
Nomenclature NACRES :
NA.22

27,10 €

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Niveau de qualité

100

Essai

97%

Forme

solid

Capacité de réaction

reaction type: Arylations
reaction type: Cross Couplings
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling

Pf

164 °C (lit.)

Groupe fonctionnel

phosphine

Chaîne SMILES 

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

Clé InChI

MYSMMEUXKHJYKH-UHFFFAOYSA-O

Description générale

Tricyclohexylphosphine tetrafluoroborate (PCy3·HBF4) is an inexpensive and air-stable phosphine ligand, commonly used in cross-coupling reactions.[1]

Application

Tricyclohexylphosphine tetrafluoroborate may be used in the following processes:
  • As a ligand for preparing C-homoaporphine alkaloids via microwave-assisted direct-arylation.[2]
  • 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.[3]
  • To improve the reactivity of palladium-catalyzed Suzuki-Miyaura cross-coupling reaction between MIDA boronates and less activated alkenyl tosylates.[1]
Used with Ru(cod)Cl dimer to catalyze the dehydrogenative coupling of alcohols and amines to form amide bonds.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Certificats d'analyse (COA)

Lot/Batch Number
WXBD8367V
SHBJ3762
23796EMV
23796EM
15107CJ

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

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

Greener Methods: Catalytic Amide Bond Formation

We are proud to offer a number of products used in catalytic amidation technology.

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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