638064

XPhos

98%

• Synonym(s): 2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl
• Empirical Formula (Hill Notation): C₃₃H₄₉P
• CAS Number: 564483-18-7
• Molecular Weight: 476.72
• MDL number: MFCD04117682
• UNSPSC Code: 12352103
• PubChem Substance ID: 24882906
• NACRES: NA.22

Properties

• Quality Level: 300
• Assay: 98%
• reaction suitability: reaction type: Cross Couplings; 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
• greener alternative product score: old score: 2; new score: 1; Find out more about DOZN™ Scoring
• greener alternative product characteristics: Waste Prevention; Atom Economy; Use of Renewable Feedstocks; Catalysis; Learn more about the Principles of Green Chemistry.
• sustainability: Greener Alternative Product
• mp: 187-190 °C (lit.)
• functional group: phosphine
• greener alternative category: , Re-engineered
• SMILES string: 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
• InChI key: UGOMMVLRQDMAQQ-UHFFFAOYSA-N

Description

General description

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.

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Click here for more information.

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 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]

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

Legal Information

Usage subject to US Patent 7,223,879

Usage subject to US Patents 6307087 and 6395916.

Safety Information

• Storage Class Code: 13 - Non Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves