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638099

CyJohnPhos

97%

Synonym(s):

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

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1 g

Available to ship TODAYfromMILWAUKEE

$48.50
$36.37
5 g

Available to ship TODAYfromMILWAUKEE

$142.00
25 g

Available to ship TODAYfromMILWAUKEE

$550.00

About This Item

Empirical Formula (Hill Notation):
C24H31P
CAS Number:
Molecular Weight:
350.48
UNSPSC Code:
12352002
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
8440533

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Quality Level

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

Legal Information

Usage subject to US Patents 6307087 and 6395916.

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638439747807900621
assay

97%

assay

97%

assay

-

assay

95%

reaction suitability

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

reaction suitability

reaction type: Cross Couplings, reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction, reagent type: ligand
reaction type: C-X Bond Formation, reagent type: ligand
reaction type: Heck Reaction, reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

reaction suitability

-

reaction suitability

-

functional group

phosphine

functional group

phosphine

functional group

phosphine

functional group

phosphine

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

mp

102-106 °C (lit.)

mp

86-88 °C (lit.)

mp

178-183 °C (decomposition without melting)

mp

-

product line

Buchwald Ligand

product line

-

product line

Buchwald precatalyst Generation 2

product line

Buchwald precatalyst Generation 3


hcodes

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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Articles

Buchwald phosphine ligands for C-C, C-N, and C-O bond formation.

Buchwald and coworkers develop versatile phosphine ligands for Pd-catalyzed C–N bond formation; enhancing synthetic reactions for 20 years.

Buchwald phosphine ligands for C-C, C-N, and C-O bond formation.

View All Articles

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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



Global Trade Item Number

SKUGTIN
638099-1G04061826724408
638099-25G04061833510230
638099-5G04061833499535

Questions

1–2 of 2 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    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/418/501/product-dating-information-06-25-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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