RuPhos Pd G2 - ≥97% , CAS No.1375325-68-0

CAS: 1375325-68-0 Cat. No.: R138190 Fórmula: C₄₂H₅₃ClNO₂PPd Peso molecular: 776.72 Número EC: 814-470-7 PubChem CID: 249818022

GRADE & PURITY ≥97%

Synonyms

Umicore CX123 - Pd(RuPhos)G2

Storage

Room temperature,Argon charged

Shipped In

Normal

Descripción general

Product Introduction
RuPhos Pd G2 is a second generation (G2) precatalyst containing a biphenyl-based ligand. Product participates in various palladium catalyzed cross-coupling reactions, C-C, C-N, and C-O bond formation reactions and Suzuki-Miyaura coupling reactions. It generates active Pd catalyst at room temperature in the presence of weak phosphate or carbonate bases.

Product Usage

RuPhos Pd G2 can be used as a precatalyst for the preparation of fluorine-substituted diazotetraene and diazopentanitrogen by Pd-catalyzed arylamination.

Product class

M-P, Homogeneous Catalysts, M-N, Buchwald Catalyst, Buchwald Catalyst 2nd Generation, Amino Ligands, Phosphorus Ligands - Achiral

Reaction type

Cross Coupling Reactions with Arenes, Amination, Buchwald-Hartwig Aminaton, Suzuki-Miyaura Coupling Reaction

Chemical properties

Chemical formula

C42H53ClNO2PPd

Empirical formula

Pd(RuPhos)[2-(2'-amino-1,1'-biphenyl)]Cl

Molecular weight

776.73

Metal

Pd

Theoretical metal content

14

Physical state

powder

Color

white

Specifications

Sinónimos

Umicore CX123 - Pd(RuPhos)G2

Especificaciones y pureza

≥97%

Condiciones de almacenamiento de almacenamiento

Room temperature,Argon charged

Enviado en

Normal

Pureza

≥97%

Nombres e identificadores

Pubchem Sid

504773765

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/504773765

PubChem CID

249818022

Peso molecular

776.72

Propiedades químicas y físicas

• Punto de fusión (°C): 195-197 °C

Application Protocols

No assay protocols are specified for this item. As a catalytic reagent, it is used in synthetic reaction setups rather than bioassays.

General setup example (literature; not product-specific)

• Charge a dry vessel with aryl halide (1.0 equiv), amine/phenol/boronate (1.2–1.5 equiv), base (1.5–3.0 equiv), RuPhos Pd G2 (0.5–1.0 mol% Pd), and solvent (0.1–0.5 M).
• Degas/argon backfill if desired; heat to 80–100 °C with stirring until completion by TLC/GC/HPLC.
• Cool, quench with aqueous NH4Cl, extract, and purify. Include a Pd-scavenging step for sensitive applications.

For validated, item-specific protocols and mol% recommendations, consult the primary literature and your internal method development data.

Biological Roles

This product is a synthetic organometallic precatalyst for laboratory synthesis and has no intrinsic biological role.

General context (literature)

• Palladium–phosphine complexes are not natural metabolites and do not participate in cellular pathways. Any observed biological effects would be non-specific (e.g., metal/protein interactions) and are outside the usual intended research use.
• RuPhos is a bulky biaryl phosphine tailored for catalysis and has no known physiological function.

Research use note (from Product Data)

• For research use only.

Buffer Applications

Not typically applicable. RuPhos Pd G2 is used as a homogeneous cross‑coupling catalyst rather than as a buffering agent.

Practical note

• If reactions are conducted in aqueous or biphasic media, buffers may be used to control pH for substrate stability (e.g., carbonate/phosphate for Suzuki couplings), but the catalyst itself does not provide buffering capacity.

Green Alternatives

Greener solvent/catalyst strategies (literature; balance performance vs EHS)

• Solvents:
  • Replace THF/dioxane with 2-MeTHF or CPME for C–N/C–O couplings (similar kinetics; improved safety and biorenewable content for 2‑MeTHF).
  • Use ethanol or water/ethanol mixtures for Suzuki reactions when compatible with substrates; leverage inorganic bases (K2CO3, K3PO4).
  • Micellar catalysis (aqueous surfactants such as TPGS-750-M) enables low organic solvent usage; validate RuPhos Pd G2 compatibility.
• Bases:
  • Favor inorganic carbonates/phosphates over strong alkoxides when feasible to minimize hazards and waste.
• Catalyst and metal economy:
  • Employ low Pd loadings (≤0.5 mol%) and catalyst recycling via scavengers or supported Pd for workup. Consider Ni catalysts (e.g., Ni/ligand systems) for certain aryl halides as Pd-sparing alternatives.

Comparison snapshot (literature; qualitative)

• 1,4-Dioxane vs 2-MeTHF: Similar performance; 2‑MeTHF has better green metrics (renewable feedstock, lower peroxide risk than ethers like THF, though still monitor peroxides).
• DMF/DMAc vs EtOH/H2O: Polar aprotics often faster but carry regulatory and EHS burdens; hydroalcoholic systems greener but may require higher temps or phase-transfer aids.

Implementation tips

• Start with 2‑MeTHF or toluene for C–N couplings; for Suzuki, try EtOH/H2O + K3PO4 at 60–80 °C with 0.5–1 mol% Pd.
• Apply process mass intensity (PMI) tracking and metal scavenging to reduce downstream environmental impact.

Pharmaceutical Uses

No therapeutic or clinical use is claimed or implied.

Formulation/manufacturing context (literature/general)

• Role in pharma R&D and process chemistry: Catalyst for assembling biaryl, aryl–amine, and aryl–ether motifs during API/intermediate synthesis via Buchwald–Hartwig, Suzuki–Miyaura, and related couplings.
• Regulatory considerations: Residual palladium and phosphine ligand must be controlled per ICH Q3D/Q3A/B; processes typically include metal scavenging (S, N, or π-acceptor resins), carbon treatments, and rigorous purification.
• Solvent choices and workup are often optimized to minimize extractables/leachables and meet impurity specifications.

Note

• This product is for research/laboratory use only (per Product Data).

Physical Properties

Item-specific (from Product Data)

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight (item): Not specified for this item; refer to CoA/Spec Sheet.

Literature/general properties (guidance; not specifications)

• Physical state: Typically an air-stable solid for bench handling in dry conditions, often yellow to orange for many G2 analogs (exact appearance for this SKU not specified).
• Solubility profile: Good solubility in common organic solvents used for cross-coupling such as toluene, THF, dioxane, EtOAc, and polar aprotic media (DMF/DMAc). Solubility can improve with gentle warming and sonication. Water insoluble.
• Thermal behavior: G2 precatalysts are generally thermally robust up to typical coupling temperatures (80–120 °C) when dissolved in organic media under inert atmosphere.
• Hygroscopicity: Not strongly hygroscopic, but prolonged exposure to moisture/air may degrade performance.
• UV–vis: Pd–phosphine charge-transfer bands are often observed in the UV region; specific λmax for this item is not specified.

Important note

• Do not treat the above as product specifications. For exact assay, water, inorganic content, or residual ligand/halide analyses, consult the item’s CoA/Spec Sheet (Not specified for this item; refer to CoA/Spec Sheet).

Quality and Grades

Item-specific (from Product Data)

• Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

General guidance on quality for Pd precatalysts (literature/practice)

• Catalyst integrity: For pre-formed Buchwald G2 complexes, the proportion of intact precatalyst versus partially reduced or ligand-dissociated species affects induction time and reproducibility.
• What to check on CoA/Spec Sheet: Identity (NMR, HRMS, elemental analysis), assay/purity (%), residual solvents, halide content, Pd assay, ligand:Pd ratio, water content (KF), and appearance.
• UV purity/HPLC grade: Not typically specified for catalysts; however, LC or HPLC area% may be reported to support purity claims. If UV cutoff or trace metal contaminants are critical for your process, confirm by CoA (Not specified for this item; refer to CoA/Spec Sheet).
• Stabilizers: Many G-series precatalysts require no external stabilizer; any stabilizer present would be stated on the CoA (Not specified here).

Practical notes

• Batch-to-batch reproducibility is essential for scale. Request the CoA lot-matched to your shipment.
• If conducting pharma or GMP-adjacent work, document trace impurity profiles and residual phosphine content per your internal quality systems.

Reaction and Applications

Scope (literature/general; expand from known use of RuPhos precatalysts)

• C–N coupling (Buchwald–Hartwig amination): Primary/secondary amines, anilines, benzylamines with aryl bromides/chlorides/triflates. RuPhos increases activity toward less activated aryl chlorides.
• C–O coupling: Phenol and alcohol arylation to aryl ethers; bulky ligand helps suppress β-hydride elimination with benzyl alcohols.
• C–C coupling: Suzuki–Miyaura of aryl halides/boronic acids/esters; t-BuOH/H2O or toluene/dioxane with K3PO4 frequently effective.
• C–S coupling: Thiol arylation to thioethers under mild conditions; manage catalyst poisoning by sulfhydryls via base and dilution.
• Nucleophilic substitutions on heteroaryl halides: Good tolerance to N-containing heterocycles due to electron-rich ligand.

Practical advantages (literature)

• Short induction times (G2 platform) via rapid in situ formation of L–Pd(0).
• Low catalyst loadings (often 0.25–2 mol% Pd) feasible on many substrates.
• Robust to moderate moisture/air if handled reasonably, though inert technique is recommended for reproducibility.

Tips

• Dry base and solvent improve consistency; preheat solvent for sluggish aryl chlorides.
• For hindered amines, increase temperature or switch to stronger base (NaOtBu) and higher ligand:Pd exposure if using blended systems.
• If protodeboronation competes in Suzuki couplings, reduce temperature and use less basic media (K2CO3, pH-neutral buffered water).

Note: Always validate on your substrate; performance varies with electronics/sterics.

Reaction Conditions

General literature guidance (optimize per substrate; values are not specifications for this item)

Buchwald–Hartwig amination (aryl chloride example)

• Catalyst: RuPhos Pd G2 (0.5–2 mol% Pd)
• Base: NaOtBu (1.5–2.0 equiv) or K3PO4/Cs2CO3 for milder conditions
• Solvent: Toluene, 1,4-dioxane, or 2‑MeTHF
• Temperature: 80–110 °C
• Time: 2–12 h; often complete in <6 h for activated substrates
• Notes: Hindered amines may require higher temp or 2 mol% Pd; use dry glassware and inert atmosphere.

Suzuki–Miyaura coupling

• Catalyst: 0.25–1 mol% Pd
• Base: K3PO4 (2–3 equiv), K2CO3, or Cs2CO3
• Solvent: Toluene/H2O, dioxane/H2O, EtOH/H2O; optional phase-transfer additive
• Temperature: 50–90 °C
• Notes: Lower temps reduce protodeboronation with sensitive boronates; maintain slight water content to activate boron species.

C–O/C–S couplings

• Base: NaOtBu or K3PO4 (1.5–2.5 equiv)
• Solvent: Dioxane, 2‑MeTHF, CPME
• Temperature: 60–100 °C
• Notes: For thiols, keep concentrations low to mitigate catalyst poisoning.

Workup hints

• Quench with aqueous NH4Cl or dilute acid, extract with EtOAc, polish with activated carbon if colored, and scavenge Pd if needed (silica–thiol, mercaptopropyl resins).

Safety and Handling

Item-specific hazard information

• GHS classification: Not specified for this item; refer to SDS.
• Signal word / H-Statements / Pictograms: Not specified for this item; refer to SDS.

General safety guidance for Pd–phosphine precatalysts (literature/practice)

• Expected hazards: May cause skin/eye irritation; harmful if swallowed; hazardous to aquatic life due to heavy metal content.
• PPE: Wear lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Handle powders in a fume hood to avoid dust inhalation.
• Incompatibilities: Strong oxidizers; strong acids/bases in the presence of air/moisture can promote decomposition. Avoid halogenating agents and fine metal powders that could induce unwanted catalytic reactions.
• Special risks: Finely divided palladium compounds can catalyze unintended reactions (e.g., hydrogenation in the presence of H2 sources). Phosphine ligands can have odor/toxicity; prevent exposure.
• First aid (overview, defer to SDS): If on skin/eyes, rinse with water for ≥15 min; seek medical advice. If inhaled, move to fresh air; if ingested, rinse mouth, do not induce vomiting, and seek medical attention.
• Waste: Collect Pd-containing wastes and contaminated disposables as hazardous heavy‑metal waste. Do not discharge to drains.

Storage and handling practices

• From Product Data: Store at room temperature, argon charged. Ship normal.
• Practice: Keep tightly closed under inert gas, in a dry cabinet or desiccator. Minimize light and moisture exposure to preserve catalytic performance.

Solvent Selection

Context: RuPhos Pd G2 is used catalytically; solvent choice impacts activation rate, oxidative addition, and base solubility.

General solvent guidance (literature)

• Nonpolar aromatics: Toluene, xylenes — good for many C–N and C–C couplings with strong bases (NaOtBu, KOtBu). High boiling and low polarity reduce side reactions.
• Ethers: THF, CPME, 2-MeTHF, dioxane — balance polarity and coordination; often effective for aryl chloride/bromide aminations and C–O couplings.
• Polar aprotics: DMAc, DMF, NMP, DMSO — enhance rates with less reactive electrophiles or weaker bases (K3PO4, Cs2CO3); consider workup and solvent removal.
• Alcoholic/aqueous systems: With phase-transfer or micellar conditions, RuPhos-based catalysts can operate in EtOH/H2O or surfactant media; verify stability for your substrate set.

Selection tips

• For challenging aryl chlorides: Start with toluene or dioxane at 80–110 °C with NaOtBu/K3PO4.
• For polar nucleophiles (e.g., amines with salts): DMAc/DMSO or dioxane/water (5–20%) can increase rates.
• Green balance: 2-MeTHF or CPME often match THF performance but with better safety/greenness.

Comparison snapshot (literature)

• Toluene: High selectivity, easy product isolation; higher temp required.
• 1,4-Dioxane: Versatile for C–N/C–O; peroxide monitoring needed.
• 2-MeTHF/CPME: Greener ethers; broader liquid range; good for scale.
• DMAc/DMF: Fast kinetics; regulatory scrutiny and difficult removal on scale.

Storage and Reconstitution

Item-specific (from Product Data)

• Storage conditions: Room temperature, argon charged.
• Shipped in: Normal.

General handling guidance (literature/practice)

• Keep container tightly sealed under inert gas (Ar or N2). Store in a dry place away from moisture and oxidants. Protect from prolonged light exposure.
• Short-term bench handling is typically acceptable, but return promptly to inert storage to preserve activity.

Solution preparation

• Reconstitution is not applicable in the biophysical sense; to prepare stock solutions, dissolve the solid in anhydrous organic solvent (e.g., toluene, THF, 2‑MeTHF, dioxane, DMAc) under inert atmosphere.
• Typical stock concentrations: 5–50 mM in dry solvent. Filter through a PTFE syringe filter if particulates are present.
• Storage of solutions: Use fresh when possible. If storage is necessary, keep under argon in crimped/septum vials at ambient to refrigerated temperature and protect from air/moisture; test a small aliquot for activity before critical runs.

Stability note

• Exact shelf-life and solution stability are Not specified for this item; refer to CoA/Spec Sheet. As with most Pd–phosphine precatalysts, minimizing air/moisture contact maintains performance.

Structure and Identity

Brief: RuPhos Pd G2 is a second‑generation Buchwald precatalyst comprising Pd(II) bound to the bulky biaryl phosphine ligand RuPhos. It is designed to rapidly generate the active L–Pd(0) species for cross‑coupling.

Item-specific (from Product Data)

• SKU: R138190
• Product name: RuPhos Pd G2
• CAS: 1375325-68-0
• CID: 249818022
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general identity (for context; not item-specific specifications)

• Compound class: Pre-formed Pd(II)–biarylphosphine complex ("G2" Buchwald precatalyst family) bearing RuPhos [2‑dicyclohexylphosphino‑2′,6′‑diisopropoxy-1,1′-biphenyl] as the supporting ligand.
• Structural features: Square-planar Pd(II) center ligated by RuPhos and an anionic ligand set that releases an active RuPhos–Pd(0) under base. The bulky, electron-rich biaryl phosphine accelerates oxidative addition and stabilizes low-valent Pd.
• 2D description: A biaryl phosphorus donor with two cyclohexyl substituents on P and two isopropoxy groups on the remote aryl ring; coordinated to a Pd center with a leaving group arrangement characteristic of G2 precatalysts (precatalyst scaffold varies across the G1–G4 series).

Synthetic Utility

Key functional elements (literature)

• Electron-rich, bulky RuPhos ligand promotes rapid oxidative addition to aryl chlorides/bromides, stabilizes Pd(0), and favors reductive elimination in C–N/C–O/C–C couplings.
• G2 platform minimizes induction time by generating L–Pd(0) under mild base, enabling low loadings and short cycle times.

Applications

• Construction of diarylamines, aryl piperidines/morpholines, and hindered anilines via Buchwald–Hartwig amination.
• Formation of aryl ethers and thioethers from phenols/thiols.
• Biaryl formation (Suzuki–Miyaura) including heteroaryl–aryl unions prone to protodeboronation.

Retrosynthetic value

• Converts challenging aryl chlorides to versatile aryl–X disconnections, enabling use of inexpensive electrophiles.
• Tolerates many functional groups (esters, nitriles, amides, sulfonamides), aiding convergent, late-stage diversification.

Practical guidance

• Match base/nucleophile: Strong, non-nucleophilic bases (NaOtBu) for hindered aminations; milder bases (K3PO4/Cs2CO3) to protect sensitive partners.
• Use inert atmosphere to preserve catalyst longevity; pre-activation is generally unnecessary with G2 but preheating can help sluggish systems.

Target Specificity

Not applicable. This product is a small‑molecule organometallic precatalyst and is not an antibody, probe, or biologic. No antigen/epitope specificity, species reactivity, clone, or isotype information applies.