XPhos
≥98%, ISOM8™
Greener Alternative
Synonym(s):
XPhos, 2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl, 2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl
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About This Item
product line
ISOM8™
Quality Segment
assay
(HPLC), ≥98%
form
solid
mol wt
476.72
reaction suitability
reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: C-C Bond Formation, reaction type: Cross Couplings, reaction type: Heck Reaction, reaction type: Hiyama Coupling, reaction type: Negishi Coupling, reaction type: Sonogashira Coupling, reaction type: Stille Coupling, reaction type: Suzuki-Miyaura Coupling, reagent type: ligand
greener alternative product score
old score: 2
new score: 1
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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
187-189 °C (Lit.), 187-190 °C (lit.)
application(s)
diagnostic assay manufacturing
functional group
phosphine
greener alternative category
storage temp.
room temp
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
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” and “Design for Energy Efficiency”. Click here to view its DOZN scorecard.
Application
XPhos, a powerful phosphine ligand developed by the developed by the Buchwald group, , significantly enhances palladium-catalyzed cross-coupling reactions for forming C-C, C-N, and C-O bonds, making it an indispensable tool in modern synthetic chemistry. Integration of XPhos into synthetic methodologies improves reaction efficiency, selectivity, and reliability while supporting both research-scale investigations and scalable manufacturing processes.
Notable Characteristics & Key Uses
- Steric Effects: The bulky dialkyl biphenyl phosphine structure — featuring a 2,4,6-triisopropylphenyl flanking ring — provides steric protection that stabilizes the palladium center during catalytic processes and controls substrate approach and coordination.
- Electronic Properties: XPhos exhibits strong sigma-donor properties, facilitating the formation of stable, highly reactive palladium complexes. Its well-balanced steric and electronic profile enhances catalytic activity and selectivity across diverse reaction conditions and substrate types.
- Cross-Coupling Reactions: XPhos plays a pivotal role in Suzuki-Miyaura, Buchwald–Hartwig, Heck, and other palladium-catalyzed cross-coupling reactions, enabling efficient carbon–carbon and carbon–heteroatom bond formation.
- Amination Reactions: Enables highly effective palladium-catalyzed amination of aryl halides and related substrates, providing direct access to aromatic amines and a broad range of nitrogen-containing compounds — including challenging primary and secondary amines.
- Pharmaceutical & Agrochemical Synthesis: Due to its ability to facilitate the construction of complex molecular architectures, XPhos is widely employed in the synthesis of pharmaceutical compounds and agrochemicals, accelerating the development of new drug candidates.
- Diverse Substrate Compatibility: XPhos accommodates a broad array of substrates, including sterically hindered electrophiles, aryl and heteroaryl halides, aryl chlorides, and functionalized nucleophiles, delivering consistently high yields where less capable ligands fall short.
Recent Studies and Innovations:
- Stable active precatalyst formation: PdCl₂(XPhos)₂ serves as an easily accessible and efficient precatalyst for Suzuki–Miyaura cross-coupling of aryl/vinyl sulfonates and halides with broad functional group tolerance, including free OH, NH₂, and strongly coordinating pyridine. Its utility was further showcased in the synthesis of bioactive compounds dubamine (88%) and tamoxifen (78%). (Fatih Sirindil et al., 2022).
- XPhos in Controlled Pre-Catalyst Reduction for Cross-Coupling Reactions: XPhos was used an effective Buchwald-type ligand for the controlled in situ generation of active Pd(0) catalysts. Using PdCl₂(ACN)₂/XPhos in toluene/ethanol with K₂CO₃, complete and selective Pd(II)-to-Pd(0) reduction was achieved via alcohol oxidation (Mechanism A), preventing phosphine oxidation and boronate dimerization in Suzuki–Miyaura reactions. This practical, cost-effective, and green protocol is directly applicable to cross-coupling reactions in pharmaceutical and agrochemical synthesis. (Tommaso Fantoni et al., 2025).
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Storage Class
11 - Combustible Solids
flash_point_f
Not applicable
flash_point_c
Not applicable
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