Saltar al contenido
Merck
Todas las fotos(4)

Key Documents

View All Documentation

901906

Sigma-Aldrich

SPhos

95%

Sinónimos:

2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl, S Phos

Iniciar sesiónpara Ver la Fijación de precios por contrato y de la organización
Todas las fotos(4)

About This Item

Fórmula empírica (notación de Hill):
C26H35O2P
Número de CAS:
657408-07-6
Peso molecular:
410.53
MDL number:
MFCD05861611
UNSPSC Code:
12161600
NACRES:
NA.22

assay

95%

form

powder or crystals

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: catalyst
reaction type: Cross Couplings
reagent type: ligand

mp

164-166 °C (lit.)
165.5 °C

functional group

phosphine

SMILES string

COc1cccc(OC)c1-c2ccccc2P(C3CCCCC3)C4CCCCC4

InChI

1S/C26H35O2P/c1-27-23-17-11-18-24(28-2)26(23)22-16-9-10-19-25(22)29(20-12-5-3-6-13-20)21-14-7-4-8-15-21/h9-11,16-21H,3-8,12-15H2,1-2H3

InChI key

VNFWTIYUKDMAOP-UHFFFAOYSA-N

¿Está buscando productos similares? Visita Guía de comparación de productos

General description

SPhos [2-Dicyclohexylphosphino-2′, 6′-dimethoxybiphenyl] is an air-stable, electron-rich biaryl phosphine ligand developed by the Buchwald group to enhance the reactivity of palladium catalysis during cross-coupling reactions.

Application

SPhos may be used as a ligand in the following processes:
  • Palladium catalyzed Suzuki-Miyaura cross-coupling reaction between Boc-protected aminomethyltrifluoroborate and aryl chlorides or hetaryl chlorides to form the corresponding aminomethylarenes.
  • Palladium catalyzed Suzuki-Miyaura cross-coupling reaction between 4-methyl-substituted piperidinylzinc reagent and different aryl or heteroaryl iodides to form various substituted piperidines.
  • Intramolecular Suzuki-Miyaura coupling to form the 18-membered macrocyclic ring during the multi-step synthesis of riccardin C.
Utilized in conjunction with palladium to form a highly active catalyst for C-N bond formation
Highly universal ligand for Suzuki-Miyaura coupling; aryl chlorides, hindered biaryls, heterobiaryls.

Legal Information

Usage subject to Patents: US 6307087; EP 1097158; JP 5758844; CA 2336691

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Elija entre una de las versiones más recientes:

Certificados de análisis (COA)

Lot/Batch Number
WXBD5936V
WXBD0196V
WXBC7953V

¿No ve la versión correcta?

Si necesita una versión concreta, puede buscar un certificado específico por el número de lote.

Busque por un COA

¿Ya tiene este producto?

Encuentre la documentación para los productos que ha comprado recientemente en la Biblioteca de documentos.

Visite la Librería de documentos

Fast Pd-and Pd/Cu-Catalyzed Direct C?H Arylation of Cyclic Nitrones. Application to the Synthesis of Enantiopure Quaternary ?-Amino Esters
Demory, Emilien, et al.
The Journal of Organic Chemistry, 77.18, 7901-7912 (2012)
Pd-catalyzed Suzuki?Miyaura reactions of aryl halides using bulky biarylmonophosphine ligands
Altman, Ryan A., and Stephen L. Buchwald
Nature Protocols, 2.12 (2007)
Synthesis and Suzuki-Miyaura Cross-Coupling Reactions of Potassium Boc-Protected Aminomethyltrifluoroborate with Aryl and Hetaryl Halides.
Molander GA and Shin I.
Organic Letters, 13(15), 3956-3959 (2011)
Synthesis and Suzuki?Miyaura Cross-Coupling Reactions of Potassium Boc-Protected Aminomethyltrifluoroborate with Aryl and Hetaryl Halides
Molander, Gary A., and Inji Shin.
Organic Letters, 13.15, 3956-3959 (2011)
Evidence for the formation and structure of palladacycles during Pd-catalyzed C-N bond formation with catalysts derived from bulky monophosphinobiaryl ligands.
Eric R Strieter et al.
Angewandte Chemie (International ed. in English), 45(6), 925-928 (2005-12-29)
Ver todos los artículos relacionados

Nuestro equipo de científicos tiene experiencia en todas las áreas de investigación: Ciencias de la vida, Ciencia de los materiales, Síntesis química, Cromatografía, Analítica y muchas otras.

Póngase en contacto con el Servicio técnico