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XPhos

Name: XPhos
Brand: ALDRICH

98%

Synonym(s):

2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl

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About This Item

Empirical Formula (Hill Notation):

C₃₃H₄₉P

CAS Number:

564483-18-7

Molecular Weight:

476.72

NACRES:

NA.22

PubChem Substance ID:

24882906

UNSPSC Code:

12352103

MDL number:

MFCD04117682

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Properties

Quality Level

300

product line

Buchwald Ligand

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.

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

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

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.
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.
Along with platinum chloride to catalyze the hydrosilylation of terminal arylalkynes with silanes to form functionalized β-(E)-vinylsilanes.

Legal Information

Usage subject to US Patent 7,223,879

Usage subject to US Patents 6307087 and 6395916.

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Storage Class

13 - Non 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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Protocols

Cross-Coupling Reactions in Water

TPGS-750-M surfactant enables various reactions in water at room temperature, enhancing efficiency and versatility in synthesis.

Articles

Buchwald Phosphine Ligands

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