(2-Biphenylyl)-di-tert.-butylphosphin

Name: (2-Biphenylyl)-di-<I>tert.</I>-butylphosphin
Brand: ALDRICH

97%

Synonym(e):

(2-Biphenyl)-di-tert.-butylphosphin, 2-(Di-tert.-butylphosphino)-biphenyl, JohnPhos

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Lineare Formel:

C₆H₅C₆H₄P[C(CH₃)₃]₂

CAS-Nummer:

224311-51-7

Molekulargewicht:

298.40

UNSPSC Code:

12352002

NACRES:

NA.22

PubChem Substance ID:

24882938

MDL number:

MFCD01862440

Beilstein/REAXYS Number:

8322131

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Produktname

(2-Biphenylyl)-di-tert.-butylphosphin, 97%

InChI

1S/C20H27P/c1-19(2,3)21(20(4,5)6)18-15-11-10-14-17(18)16-12-8-7-9-13-16/h7-15H,1-6H3

SMILES string

CC(C)(C)P(c1ccccc1-c2ccccc2)C(C)(C)C

InChI key

CNXMDTWQWLGCPE-UHFFFAOYSA-N

assay

97%

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

mp

86-88 °C (lit.)

functional group

phosphine

Quality Level

100

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Dieser Artikel	638099	695874	675938
Sigma-Aldrich 638439 (2-Biphenylyl)-di-tert.-butylphosphin	Sigma-Aldrich 638099 CyJohnPhos	Sigma-Aldrich 695874 2-Di-tert.-butylphosphino-2′-(N,N-dimethylamino)-biphenyl	Sigma-Aldrich 675938 Me4tButylXphos
assay 97%	assay 97%	assay -	assay 96%
reaction suitability reaction type: Cross Couplings, reagent type: ligand reaction type: C-X Bond Formation, reagent type: ligand reaction type: Suzuki-Miyaura Coupling, reagent type: ligand reaction type: Buchwald-Hartwig Cross Coupling Reaction, reagent type: ligand reaction type: Heck Reaction	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	reaction suitability -	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
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 86-88 °C (lit.)	mp 102-106 °C (lit.)	mp 114-118 °C	mp 168-172 °C

Application

Bulky biarylphosphine ligand utilized in the palladium catalyzed Stille cross-coupling reaction.[1]

Bulky phosphine ligand used in a Pd-catalyzed 2,3-diarylation of α,α-disubstituted-3-thiophenemethanols via cleavage of C-H and C-C bonds.[2]

Ligand utilized in amination of aryl halides and aryl triflates.

General description

JohnPhos is a Buchwald′s sterically bulky biaryl phosphine ligand. It is a reactive dialkylbiaryl phosphine ligand which catalyzes the carbon-nitrogen bond-forming reactions.[3] Coordination chemistry of gold catalysts bearing JohnPhos as ligand has been investigated by NMR spectroscopy.[4]

Learn more about Buchwald Phosphine Ligands

Lagerklasse

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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Suzuki-Miyaura Cross-Coupling of Benzylic Bromides Under Microwave Conditions.

Steven W McDaniel et al.

Tetrahedron letters, 52(43), 5656-5658 (2011-10-04)

A procedure for benzylic Suzuki-Miyaura cross-coupling under microwave conditions has been developed. These conditions allowed for heterocyclic compounds to be coupled. Optimum conditions found were Pd(OAc)(2), JohnPhos as the catalyst and ligand, potassium carbonate as base, and DMF as the

Artamkina, Galina A.; et al.

Synlett, 2, 235-238 (2006)

Acid, silver, and solvent-free gold-catalyzed hydrophenoxylation of internal alkynes.

Marcia E Richard et al.

Beilstein journal of organic chemistry, 9, 2002-2008 (2013-11-10)

A range of arylgold compounds have been synthesized and investigated as single-component catalysts for the hydrophenoxylation of unactivated internal alkynes. Both carbene and phosphine-ligated compounds were screened as part of this work, and the most efficient catalysts contained either JohnPhos

Palladium-catalyzed selective 2,3-diarylation of alpha,alpha-disubstituted 3-thiophenemethanols via cleavage of C-H and C-C bonds.

Masaya Nakano et al.

The Journal of organic chemistry, 71(21), 8309-8311 (2006-10-10)

Alpha,alpha-disubstituted 3-thiophenemethanols undergo selective diarylation accompanied by cleavage of the C-H and C-C bonds of the 2- and 3-positions, respectively, upon treatment with aryl bromides in the presence of a palladium catalyst to give the corresponding 2,3-diarylthiophenes in good yields.

Coordination chemistry of gold catalysts in solution: a detailed NMR study.

Alexander Zhdanko et al.

Chemistry (Weinheim an der Bergstrasse, Germany), 18(46), 14732-14744 (2012-09-29)

Coordination chemistry of gold catalysts bearing eight different ligands [L=PPh(3), JohnPhos (L2), Xphos (L3), DTBP, IMes, IPr, dppf, S-tolBINAP (L8)] has been studied by NMR spectroscopy in solution at room temperature. Cationic or neutral mononuclear complexes LAuX (L=L2, L3, IMes

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Artikel

Buchwald Phosphine Ligands

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

Buchwald Phosphine Ligands

Questions

1–2 of 2 Questions

Anonymous

5 months ago

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

1 answer
1. Technical Support
  
  5 months ago
  
  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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Anonymous

a year ago

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

1 answer
1. Technical Support
  
  a year ago
  
  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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