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638099

Sigma-Aldrich

CyJohnPhos

97%

Sinónimos:

2-(Dicyclohexylphosphino)biphenyl, (2-Biphenyl)dicyclohexylphosphine, Cyclohexyl JohnPhos

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1 G
MXP 981.00
5 G
MXP 4,486.00
25 G
MXP 17,961.00

MXP 981.00

Fecha estimada de envío07 de abril de 2025

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1 G
MXP 981.00
5 G
MXP 4,486.00
25 G
MXP 17,961.00

About This Item

Fórmula empírica (notación de Hill):
C24H31P
Número de CAS:
247940-06-3
Peso molecular:
350.48
Beilstein/REAXYS Number:
8440533
MDL number:
MFCD01862441
UNSPSC Code:
12352002
PubChem Substance ID:
24882909
NACRES:
NA.22

MXP 981.00

Fecha estimada de envío07 de abril de 2025

Solicitar un pedido a granel

Quality Level

100

assay

97%

reaction suitability

reaction type: Cross Couplings
reagent type: ligand
reaction type: Arylations
reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reagent type: ligand
reaction type: C-X Bond Formation
reagent type: ligand
reaction type: Hiyama Coupling
reagent type: ligand
reaction type: Methylations
reagent type: ligand
reaction type: Negishi Coupling
reagent type: ligand
reaction type: Oxidations
reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

mp

102-106 °C (lit.)

functional group

phosphine

SMILES string

C1CCC(CC1)P(C2CCCCC2)c3ccccc3-c4ccccc4

InChI

1S/C24H31P/c1-4-12-20(13-5-1)23-18-10-11-19-24(23)25(21-14-6-2-7-15-21)22-16-8-3-9-17-22/h1,4-5,10-13,18-19,21-22H,2-3,6-9,14-17H2

InChI key

LCSNDSFWVKMJCT-UHFFFAOYSA-N

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General description

CyJohnPhos [(2-Biphenyl)dicyclohexylphosphine] is an air-stable, bulky and electron-rich monodentate biarylphosphine ligand developed by the Buchwald group to enhance the reactivity of palladium catalysis during cross-coupling reactions.

Learn more about Buchwald Phosphine Ligands

Application

CyJohnPhos may be used in combination with a nickel catalyst for the Suzuki-Miyaura arylation of tertiary benzylic acetates with aryl boroxines to produce diaryl and triaryl quaternary stereocenters.[1]
Ligand employed in the palladium-catalysed synthesis of 1,3,5-tris(2′-aminophenyl)benzene, a core building block for potential ionic receptors.[2]
Ligand for amination of aryl halides and triflates.

Legal Information

Usage subject to US Patents 6307087 and 6395916.

hcodes

H413

Hazard Classifications

Aquatic Chronic 4

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)

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Certificados de análisis (COA)

Lot/Batch Number
STBL3485
STBL1895
STBL1891
SHBQ3474
STBK5406

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

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Stereospecific Cross Couplings To Set Benzylic, All-Carbon Quaternary Stereocenters in High Enantiopurity.
Zhou Q, et al.
Journal of the American Chemical Society, 138(37), 12057-12060 (2016)
Synlett, 2027-2027 (2006)
Daichi Kakizoe et al.
Dalton transactions (Cambridge, England : 2003), 46(43), 14804-14811 (2017-10-19)
We report the synthesis and photophysical properties of Cu(i) complexes with 1,10-phenanthroline (phen) and monodentate phosphine ligands. Single crystal X-ray structural analysis revealed that these have three-coordinated trigonal planar geometries. We also found that one of them, [Cu(phen)(Johnphos)]BF
David S Surry et al.
Angewandte Chemie (International ed. in English), 47(34), 6338-6361 (2008-07-30)
Palladium-catalyzed amination reactions of aryl halides have undergone rapid development in the last 12 years, largely driven by the implementation of new classes of ligands. Biaryl phosphanes have proven to provide especially active catalysts in this context. This Review discusses
David S Surry et al.
Chemical science, 2(1), 27-50 (2011-01-01)
Dialkylbiaryl phosphines are a valuable class of ligand for Pd-catalyzed amination reactions and have been applied in a range of contexts. This review attempts to aid the reader in the selection of the best choice of reaction conditions and ligand
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