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.

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]

Legal Information

Usage subject to US Patent 7,223,879

Usage subject to US Patents 6307087 and 6395916.

Safety Information

• Storage Class: 13 - Non Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)