638064

XPhos

98%

• Synonyme(s) : 2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl
• Formule empirique (notation de Hill) : C₃₃H₄₉P
• Numéro CAS: 564483-18-7
• Poids moléculaire : 476.72
• Numéro MDL: MFCD04117682
• Code UNSPSC : 12352103
• ID de substance PubChem : 24882906
• Nomenclature NACRES : NA.22

Propriétés

• Niveau de qualité: 300
• Essai: 98%
• Capacité de réaction: reaction type: Cross Couplings
• Pertinence de la réaction: reagent type: ligand; reaction type: Buchwald-Hartwig Cross Coupling Reaction; reagent type: ligand; reaction type: C-C Bond Formation; reagent type: ligand; reaction type: Heck Reaction; reagent type: ligand; reaction type: Hiyama Coupling; reagent type: ligand; reaction type: Negishi Coupling; reagent type: ligand; reaction type: Sonogashira Coupling; reagent type: ligand; reaction type: Stille Coupling; reagent type: ligand; reaction type: Suzuki-Miyaura Coupling
• Score du produit alternatif plus écologique: old score: 2; new score: 1; Find out more about DOZN™ Scoring
• Caractéristiques du produit alternatif plus écologique: Waste Prevention; Atom Economy; Use of Renewable Feedstocks; Catalysis; Learn more about the Principles of Green Chemistry.
• sustainability: Greener Alternative Product
• Pf: 187-190 °C (lit.)
• Groupe fonctionnel: phosphine
• Autre catégorie plus écologique: , Re-engineered
• Chaîne SMILES: CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C2=C(P(C3CCCCC3)C4CCCCC4)C=CC=C2
• InChI: 1S/C33H49P/c1-23(2)26-21-30(24(3)4)33(31(22-26)25(5)6)29-19-13-14-20-32(29)34(27-15-9-7-10-16-27)28-17-11-8-12-18-28/h13-14,19-25,27-28H,7-12,15-18H2,1-6H3
• Clé InChI: UGOMMVLRQDMAQQ-UHFFFAOYSA-N

Description

Description générale

We are committed to bringing you Greener Alternative Products, which adhere to one of the four categories of Greener Alternatives . This product belongs to category of Re-engineered products, showing key improvements in Green Chemistry Principles “Waste Prevention”, “Atom Economy”, “Use of Renewable Feedstock” and “Enhanced Catalytic Activity”. Click here to view its DOZN scorecard.

XPhos [2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl] is an air-stable electron-rich biaryl monophosphine ligand² developed by the Buchwald group to enhance the reactivity of palladium catalysis during cross-coupling reactions.

Application

Ligand for increased scope of Pd-catalyzed amination and amidation via arene sulfonates, aryl halides.

Ligand used in a Pd-catalyzed Suzuki coupling leading to C-15 analogs of vindoline.[1]
Direct annulation of 2-haloanilines to indoles and tryptophans catalyzed by Pd.[2] Synthesis of regioregular polythiophenes.[3]

Preferred ligand for greener Sonogashira coupling in TPGS-750-M.

Preferred ligand for greener Sonogashira coupling in TPGS-750-M.

For small scale and high throughput uses, product is also available as ChemBeads (928364)

On the Way Towards Greener Transition-Metal-Catalyzed Processes as Quantified by E Factors

XPhos may be used as a ligand in the following reactions:

• Preparation of functionalized benzylic sulfones via palladium-catalyzed Negishi cross-coupling between alkyl sulfones and aryl halides.[4]
• Along with pre-milled palladium(II) acetate as a pre-catalyst for the Stille cross-coupling of aryl chlorides with tributylarylstannanes to form the corresponding biaryl compounds.[5]
• Along with platinum chloride to catalyze the hydrosilylation of terminal arylalkynes with silanes to form functionalized β-(E)-vinylsilanes.[6]

Informations légales

Usage subject to US Patent 7,223,879

Usage subject to US Patents 6307087 and 6395916.

Informations sur la sécurité

• Code de la classe de stockage: 13 - Non Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: Eyeshields, Gloves, type N95 (US)