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638099

CyJohnPhos

97%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C24H31P
CAS Number:
247940-06-3
Molecular Weight:
350.48
UNSPSC Code:
12352002
NACRES:
NA.22
PubChem Substance ID:
24882909
MDL number:
MFCD01862441
Beilstein/REAXYS Number:
8440533
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Quality Segment

100

product line

Buchwald Ligand

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

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

Ligand for amination of aryl halides and triflates.
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.
Ligand employed in the palladium-catalysed synthesis of 1,3,5-tris(2′-aminophenyl)benzene, a core building block for potential ionic receptors.

Legal Information

Usage subject to US Patents 6307087 and 6395916.

hcodes

H413

Hazard Classifications

Aquatic Chronic 4

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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