This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
External Descriptors
Not available
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
Determine the necessary mass, volume, or concentration for preparing a solution.
Dilution Calculator
Determine the dilution needed to prepare a stock solution.
Reconstitution Calculator
리뷰
고객 리뷰
Application Protocols
No item-specific tested applications are provided for this ligand.
General handling protocol for phosphine ligands in cross-coupling (literature guidance; adjust to your system)
Preparation: Work in a glovebox or under Schlenk conditions. Ensure all glassware is dry (oven- or flame-dried) and cooled under inert gas.
Catalyst setup: Charge vessel with Pd precursor (e.g., Pd2(dba)3 or an air-stable precatalyst), Cy‑cBRIDP (as ligand), and dry solvent. Stir briefly to pre-form the catalyst if using Pd(II).
Substrates and base: Add electrophile (aryl chloride/bromide/triflate), nucleophile (amine/boronate/alkoxide), and base. Maintain inert atmosphere.
Reaction: Heat or stir at the selected temperature; monitor by TLC/GC/HPLC. Adjust stoichiometry and temperature based on conversion/selectivity.
Workup: Cool, quench carefully (e.g., aqueous NH4Cl for aminations), extract with suitable organic solvent, dry, and concentrate. Purify by chromatography or crystallization.
Metal/ligand removal: Treat with scavengers (silica–thiol, resins) as needed to meet residual Pd/ligand targets.
Always verify conditions with small-scale experiments and consult the SDS and CoA for product-specific instructions.
Biological Roles
Applicability
Cy‑cBRIDP is a synthetic organophosphorus ligand intended for use in transition-metal catalysis. It does not have established endogenous biological roles.
General notes (for context only)
Tertiary phosphine ligands are primarily tools for synthetic chemistry and catalysis; they are not metabolites, cofactors, or biomacromolecules.
In bioconjugation or chemoproteomics, metal–ligand complexes can occasionally be used to mediate transformations on biomolecules, but such applications require stringent compatibility assessments and are outside typical biological function.
Safety and handling in bio-related labs
Avoid introducing phosphine ligands into cell culture or biochemical assays unless the study explicitly aims at catalysis under biocompatible conditions; impurities and metal residues can confound biological readouts.
Conclusion
No inherent biological function or pathway involvement is attributed to this ligand class. For any biointerface studies, treat as a non-biological reagent and consult SDS for hazard guidance.
Buffer Applications
Not typically applicable.
Cy‑cBRIDP is a hydrophobic organophosphorus ligand for catalysis and is not used to prepare buffering systems. It lacks acid–base pairs suitable for maintaining a defined pH range in aqueous media.
Guidance
If catalytic work is planned in aqueous or micellar systems, buffer choice should be driven by substrate and base compatibility (e.g., phosphate, bicarbonate, or borate buffers) and by the stability of the metal–ligand catalyst under those conditions. These selections are reaction-specific and should be optimized empirically.
Green Alternatives
Perspective
As a ligand, Cy‑cBRIDP itself is not readily replaced by a “green solvent,” but greener choices can be made in the overall catalytic system. Below are literature-based considerations for improving the sustainability profile of cross-coupling using bulky biaryl phosphines.
Greener choices (general guidance)
Solvents: favor 2‑MeTHF, CPME, anisole, toluene, or propylene carbonate over DMF, NMP, dioxane, and chlorinated solvents when compatible with reactivity and isolation.
Bases: replace Cs2CO3 with K3PO4 or K2CO3 where feasible; consider carbonate/biocarbonate in aqueous or micellar media.
Catalyst loading: bulky biaryl phosphines often enable ppm-level Pd loadings; optimizing to sub‑0.1 mol% significantly reduces metal footprint.
Aqueous/micellar catalysis: with appropriate surfactants and air-stable precatalysts, many couplings proceed in water at lower temperatures, easing solvent burden.
Ligand/catalyst recovery: immobilized catalysts or biphasic systems can facilitate recycling.
Trade-offs
Greener solvents may alter rates/solubility; higher temperature or different bases may be needed.
Lower Pd loading can increase reaction time or require more rigorous exclusion of air/moisture.
Mini comparison (illustrative, literature)
THF vs 2‑MeTHF: similar polarity; 2‑MeTHF has better renewables profile and higher bp, easing recovery.
Dioxane vs CPME: CPME offers broader stability window and lower peroxide tendency, with improved safety profile.
Adopt these alternatives case-by-case, verifying performance with your specific substrate set.
Pharmaceutical Uses
Context (no therapeutic claims)
Cy‑cBRIDP is for research use only. It is not an active pharmaceutical ingredient or excipient.
Process chemistry relevance (general)
Bulky biaryl phosphine ligands are widely used in pharmaceutical process development to enable robust Pd- or Ni-catalyzed cross-couplings (C–N, C–C, C–O) on scale, including aryl chloride activation and sterically hindered couplings.
Benefits for manufacturing include lower catalyst loadings, milder temperatures, broadened substrate scope, and improved selectivity, which can streamline synthetic routes and reduce step count.
Operational considerations
Selection of ligand/precatalyst pair is critical for reproducibility and impurity control. Air-stable precatalysts can simplify handling under GMP-like conditions.
Downstream: effective Pd scavenging (e.g., silica–thiol, metal scavenger resins) and ligand removal strategies are standard to meet metal/organic impurity limits.
Regulatory note
Ligands themselves are typically not compendial substances. Any use in regulated manufacturing requires full quality documentation (CoA, impurity profile) and validated removal of residual ligand and metal from drug substance.
Physical Properties
Item-specific values
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
BP/MP/Density/Refractive Index/UV Cutoff/Water or Peroxide content: Not specified for this item; refer to CoA/Spec Sheet.
Literature/contextual information for bulky biaryl phosphines (general guidance, not specifications)
Physical state: typically off-white to pale solids or viscous oils depending on substituents (literature, varies by analogue).
Air/moisture sensitivity: many dialkylbiarylphosphines are air-sensitive to varying degrees and may oxidize to phosphine oxides; solutions in dry, oxygen-free solvents are commonly used.
Solubility (typical, literature): good solubility in nonpolar to moderately polar aprotic organic solvents (toluene, THF, dioxane, DCM, MTBE, CPME); low solubility in water.
Partitioning: high hydrophobicity is common due to bulky alkyl/aryl substituents.
Practical notes (general)
Handle under inert atmosphere to avoid slow oxidation; minimize exposure to air/light and elevated temperature.
If crystalline, melting behavior can be depressed by residual solvent; drying under vacuum at low temperature is typical to preserve ligand integrity.
For precise physical constants and acceptance criteria applicable to this SKU, please consult the product’s CoA/Spec Sheet.
Quality and Grades
Item-specific grade/purity
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
What to expect for high-end ligand materials (general guidance)
Ligand quality impacts catalytic performance profoundly. Trace oxidation (phosphine oxide), residual solvents, halides, and metals can depress activity or change selectivity.
Typical quality controls for premium phosphine ligands include: 31P NMR assay (to quantify free phosphine vs oxide), 1H/13C NMR identity/purity, HRMS or elemental analysis, residual solvent profiling (GC), and Karl Fischer moisture if applicable. UV profile is less relevant unless ligand used in photochemical contexts.
Interpreting grades (general)
“Catalyst/ligand grade” commonly signals high purity and low phosphine oxide content, packed and stored under inert gas.
“Screening” vs “process” grades: screening grade focuses on usability for discovery; process grade may include tighter specifications (e.g., lower residual metals, tighter 31P assay, validated impurity profile) for scale-up.
Stabilizers and packaging
Some phosphines are supplied pre-charged with inert gas (as here) and may include oxygen scavengers or be vacuum-sealed with septum-accessible vials. This product is specified to be argon charged; maintain inert atmosphere upon opening.
For the definitive acceptance criteria, impurity limits, and certification applicable to SKU C153988, consult the CoA/Spec Sheet.
Reaction and Applications
Context
Cy‑cBRIDP belongs to the family of bulky, electron-rich biaryl phosphines widely used to accelerate cross-coupling chemistry. The points below summarize common uses for this ligand class (literature); apply as general guidance rather than item-specific claims.
Representative transformations (literature)
C–N bond formation: Buchwald–Hartwig amination of (hetero)aryl halides/triflates with amines, amides, and anilines; notable for enabling aryl chlorides and hindered substrates.
C–C coupling: Suzuki–Miyaura (with aryl boronates), Negishi (organozincs), Kumada (Grignards), Stille (organostannanes), and Hiyama (organosilanes) couplings with challenging electrophiles.
C–O and C–S coupling: aryl etherification and thioetherification with alkoxides/thiolates, including sterically encumbered phenols.
Reductive couplings and carbonylations: in selected systems with Pd/Ni under CO or reductants.
Why bulky biaryl phosphines?
Large cone angle and strong σ-donation promote fast oxidative addition and stabilize low-coordinate metal centers, enabling low catalyst loadings and lower temperatures.
Steric protection can suppress β-hydride elimination and off-cycle aggregation, improving chemoselectivity and catalyst longevity.
Practical guidance
Use rigorously dry, degassed solvents and bases. Pre-activation with Pd(II) precatalysts (e.g., palladium–(η3-allyl) or “G3/G4” systems) enhances reproducibility.
Explore base/solvent pairs: K3PO4 or K2CO3 in toluene/dioxane; NaOtBu or KOtBu in t-BuOH/THF; Cs2CO3 in dioxane or toluene/water biphasic systems.
Substrate scope and optimal conditions are substrate-specific; perform small-scale screens to identify the best combination.
Reaction Conditions
General literature guidance for bulky biaryl phosphine–enabled couplings (not item-specific; optimize per substrate)
Catalyst: Pd(OAc)2 or Pd2(dba)3 (0.1–1.0 mol% Pd) with ligand (0.2–2.0 mol%).
Base: K3PO4, K2CO3, Cs2CO3, or Na2CO3 (aqueous or anhydrous).
Solvent: toluene/H2O, dioxane/H2O, 2‑MeTHF/H2O, or alcohol/water mixtures.
Temperature: rt–100 °C; time: 1–12 h; consider micellar media for greener conditions.
C–O/C–S coupling
Catalyst: Pd(0/II) with bulky biaryl phosphine (1–3 mol%).
Base: NaOtBu, KOtBu, or K3PO4.
Solvent: toluene, dioxane, or CPME; 70–120 °C.
Ni-catalyzed variants
For activated electrophiles, NiCl2(dppp) or Ni(cod)2 with bulky monophosphine ligands; temperatures often 25–80 °C.
Notes
Degas solvents (sparging or freeze–pump–thaw). Use glovebox/Schlenk techniques. Monitor by GC/HPLC. Scale-up: ensure adequate heat/mass transfer and O2 exclusion.
Yields vary widely by substrate; consult primary literature for your substrate class.
Safety and Handling
Item-specific hazard data
Signal Word: Not specified for this item; refer to SDS.
H-Statements: Not specified for this item; refer to SDS.
GHS Classification/Pictograms: Not specified for this item; refer to SDS.
General safety guidance for tertiary phosphine ligands (literature/class-based)
Hazards: air- and moisture-sensitive ligands may form phosphine oxides; some phosphines are skin/eye irritants and harmful if swallowed or inhaled. Avoid inhalation of dust/fumes and skin contact. Many dialkylphosphines have strong, unpleasant odors; work in a fume hood.
Special risks: oxidation on air; slow peroxide formation is not typical for phosphines (more relevant to ethers) but autoxidation to phosphine oxides is common. Metal-catalyst residues in reaction mixtures can produce toxic fumes on heating—use proper quench and workup.
Incompatibilities: strong oxidizers (may cause rapid oxidation), strong acids (possible protonation), halogenating agents. Avoid prolonged exposure to air, heat, and light.
PPE: lab coat, chemical-resistant gloves (e.g., nitrile), splash goggles; consider double-gloving for extended handling. Use within a certified chemical fume hood or glovebox.
First aid (overview; defer to SDS):
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: rinse with water for ≥15 min; remove contaminated clothing; seek medical attention if irritation develops.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Always consult the product-specific SDS for authoritative safety and emergency information.
Solvent Selection
Applicability
Cy‑cBRIDP is a ligand rather than a solvent; solvent selection is relevant in the context of the catalytic reactions it enables.
General solvent guidance for bulky biaryl phosphine–enabled cross-couplings (literature)
Common solvents: toluene, xylene, anisole, 1,4-dioxane, THF, 2-MeTHF, CPME, MTBE, DME, DMAc, DMF, NMP, acetonitrile, and alcohols (t-BuOH, n-BuOH) depending on substrate/base.
Selection criteria:
Solubility of ligand, metal precursor, base, and substrates.
Thermal stability at required temperature.
Compatibility with base (e.g., alcohols with alkoxides; amide solvents with strong bases can cause degradation).
Green metrics (boiling point, safety, recyclability).
Water and aqueous micellar media are increasingly used with specialized catalyst systems; however, air-stable precatalysts and surfactants are typically required.
Small comparison (general)
Toluene/xylene: good for high-temperature couplings; low polarity favors some oxidative additions.
Dioxane/THF/2-MeTHF/CPME: ether media balance polarity and solubility; 2-MeTHF/CPME are greener alternatives to THF/dioxane.
Polar aprotics (DMAc/DMF/NMP): enhance rates for challenging aryl chlorides but have EHS concerns; consider alternatives like propylene carbonate or Cyrene where compatible.
Practical tips
Degas solvents (sparging or freeze–pump–thaw). Dry ethers/aryl solvents are preferred to reduce ligand oxidation and maintain catalyst activity.
Storage and Reconstitution
Item-specific storage and shipping
Storage Conditions: Store at 2–8 °C, Argon charged (from Product Data).
Shipped In: Wet ice (from Product Data).
General handling and preservation (literature guidance for phosphine ligands)
Upon receipt: Keep container sealed until ready to use. Warm to room temperature under inert gas before opening to avoid moisture condensation.
Inert atmosphere: Maintain argon/nitrogen blanket during transfers. Minimize headspace O2 by backfilling and recap promptly. Consider septum-capped vials for syringe access.
Protection from oxidation: Store in the original argon-charged packaging or in a glovebox. Avoid repeated freeze–thaw/air exposure cycles.
Stock solutions: If solution use is preferred, prepare in dry, degassed solvents (e.g., toluene, THF, 2‑MeTHF). Store in sealed, inerted vials at 2–8 °C or −20 °C. Check 31P NMR periodically to assess oxidation (general recommendation).
Disposal: Treat as organic phosphorus waste; follow institutional and local regulations.
Reconstitution
Physical form is not specified for this item; refer to CoA/Spec Sheet. If provided as a solid, dissolve the required amount under inert gas in a dry, oxygen-free solvent of choice. If provided as a solution, use as received under inert atmosphere.
Note
For any item-specific stability limits, allowable freeze–thaw cycles, and container-closure details, consult the CoA/Spec Sheet.
Structure and Identity
Item-specific identifiers (from Product Data)
SKU: C153988
Product Name: Cy-cBRIDP
CAS: 1023330-38-2
InChIKey: 157513 (as provided; note: not in standard InChIKey format)
Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/context (general information for the BRIDP ligand family)
Cy‑cBRIDP is commonly referenced in the literature as a bulky, electron-rich, biaryl dialkylphosphine ligand (BRIDP family) bearing cyclohexyl (Cy) substituent(s) on phosphorus. Such ligands are designed to accelerate oxidative addition and stabilize low-coordinate Pd(0)/Pd(II) and Ni(0)/Ni(II) centers.
Structural features (general, literature):
One trivalent phosphorus (tertiary phosphine) strongly σ-donating, weakly π-accepting.
A rigid biaryl backbone that enforces a large cone angle and creates a protected metal pocket.
“Cy” denotes cyclohexyl groups bound to P in many members of this class, enhancing steric bulk and electron donation.
2D structure description (generic for biaryl dialkylphosphines)
A biphenyl core with an ortho-substituted phosphine on one ring; the phosphorus carries two bulky alkyl groups (often cyclohexyl), while the second aryl ring may bear additional ortho substituents that tune bite angle and steric profile.
Important note
Exact constitution (substituent pattern, stereochemistry, and full identifiers) for this specific SKU is Not specified for this item; refer to CoA/Spec Sheet.
Synthetic Utility
Functional role
Cy‑cBRIDP functions as a strongly donating, sterically demanding tertiary phosphine tailored for cross-coupling catalysis. The combination of high electron density at phosphorus and a congested biaryl framework enhances rates of oxidative addition to aryl (pseudo)halides and stabilizes active catalysts.
Retrosynthetic value (general, literature)
Enables disconnections relying on late-stage installation of amines, aryls, alkoxides, and thiolates via Pd- or Ni-catalyzed couplings, even on deactivated or hindered aryl chlorides.
Facilitates convergent synthesis by tolerating diverse functional groups under milder conditions (e.g., esters, nitriles, heteroarenes), thereby simplifying protection/deprotection sequences.
Named reactions and motifs
Buchwald–Hartwig amination, Suzuki–Miyaura, Negishi, Kumada, and etherification reactions are typical arenas where bulky biaryl phosphines excel.
Practical tips
Ligand-to-metal ratios: often 1–2 equiv vs Pd for Pd(II) precursors; precatalysts may contain a defined ligand stoichiometry.
Pre-formation of L–Pd(0) in situ vs use of single-component precatalysts can affect induction time and reproducibility.
Choice of base and solvent strongly influences selectivity and rate; begin with literature precedent for your substrate class and adjust sterics/electronics via ligand if needed.
Target Specificity
Not applicable.
This product is a small-molecule ligand for metal catalysis, not a biological targeting reagent (e.g., antibody, inhibitor with defined biomolecular target, or probe). No antigen/epitope specificity, clone, isotype, or species reactivity applies.
We use cookies to ensure the website functions properly and, where permitted, to improve your experience. You can manage your preferences at any time in Settings. Learn more in our Cookie Policy.
Shall we send you a message when we have discounts available?
Remind me later
Thank you! Please check your email inbox to confirm.
Products are supplied to verified businesses, institutions, and qualified professionals for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
