This compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
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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.
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Application Protocols
No assay-validated application protocols are provided for this item. For general coordination chemistry work, the following non‑specific guidance may be useful (literature-based; not product‑validated):
Preparation of a Pt(II) chelate [PtCl2(L)]: Dissolve PtCl2(COD) (~1 eq) in DCM under N2; add Ethylenebis(diphenylarsine) (1 eq) in DCM; stir at room temperature 2–6 h. Optionally add a small amount of MeCN to assist ligand substitution. Filter, concentrate, and crystallize by hexanes diffusion. Protect from air.
Preparation of a Pd(II) complex [PdCl2(L)]: Suspend PdCl2 in MeCN to form [PdCl2(MeCN)2], then add ligand solution in DCM/MeCN and stir 1–4 h at RT. Isolate as above.
Characterization: Record 1H/13C NMR in CD2Cl2 or C6D6; collect IR (ATR) and, if available, 75As NMR. Confirm composition by HRMS and elemental analysis.
These are generic literature-style procedures and must be optimized for your specific substrates and safety constraints. Always perform small‑scale trials first and consult the SDS before beginning work.
Biological Roles
This product is a synthetic organoarsenic coordination ligand and does not have a recognized physiological role. The following points are provided as general biochemical context for trivalent arsenicals and should not be construed as medical or clinical claims.
Biochemical interactions (literature): Trivalent arsenic species can bind strongly to vicinal dithiol motifs in proteins (e.g., reduced lipoamide cofactor sites), forming stable As–S chelates that can inhibit enzymatic activity. This underlies much of the acute biochemical toxicity of As(III) compounds.
Cellular redox: As(III) can undergo oxidation to As(V) in biological milieus; corresponding changes in speciation alter protein/ligand binding preferences (hard/soft acid–base considerations).
Transport and metabolism: Simple inorganic and methylated arsenicals use aquaglyceroporins and other transporters; bulky diarylarsines such as Ethylenebis(diphenylarsine) are highly lipophilic and are not typical biological metabolites. Data specific to this compound’s biotransformation are limited.
Research relevance: Owing to strong soft‑donor character, As(III) ligands are occasionally used as probes in bioinorganic model studies (e.g., mimicking soft metal–thiolate environments), but their toxicity demands stringent containment.
No pharmacology, ADME, or clinical utility is implied for this item. Use strictly for in vitro/in vivo laboratory research under appropriate approvals and containment.
Buffer Applications
Not typically applicable. Ethylenebis(diphenylarsine) is a neutral, hydrophobic organoarsenic ligand with no acid–base functionality tailored for aqueous buffering. It is insoluble/unstable in most aqueous buffer systems and provides no defined pKa buffering range.
For laboratory work, focus instead on its role in nonaqueous coordination chemistry and homogeneous catalysis. If handling in biphasic systems is unavoidable, employ an immiscible organic phase (e.g., toluene, DCM) and ensure that the aqueous buffer does not contain strong oxidants.
Green Alternatives
Organoarsenic ligands pose inherent toxicity and environmental persistence concerns. Where feasible, alternative ligands and greener solvents should be considered.
Ligand substitutions (literature guidance):
Phosphines (e.g., dppe, dppp, dppf) or bidentate NHCs can often deliver similar coordination geometries with lower toxicological burden than arsines.
Hemilabile P,O- or N,O‑ligands may afford comparable catalytic performance in certain reactions without arsenic.
Solvent choices:
Prefer greener ethers and aromatics where compatible: 2‑MeTHF or CPME can substitute for THF/Et2O; anisole or toluene (preferably high‑recycled grade) over chlorinated solvents.
Minimize DCM/chloroform; if needed for crystallization or spectroscopic reasons, keep volumes small and recover via solvent capture.
Process considerations:
Conduct reactions at higher substrate concentration to reduce solvent use.
Use glovebox/Schlenk best practices to prolong solution stability, thereby reducing re‑preparation and waste.
Comparison snapshot (general)
Ethylenebis(diphenylarsine): Soft bidentate As donor; high toxicity potential; good solubility in organics.
dppe (bis(diphenylphosphino)ethane): Similar chelation; broader literature in catalysis; lower toxicity relative to arsines but still hazardous.
Bidentate NHCs: Strong σ‑donors; often robust to air/moisture; may enable greener solvents and lower loadings, at the expense of different electronics.
Always perform a hazard/greenness assessment (e.g., CHEM21, ACS GHS) when choosing ligands and solvents.
Pharmaceutical Uses
No excipient or compendial roles are specified for this item; refer to CoA/Spec Sheet. Organoarsenic ligands are not typical pharmaceutical excipients or processing aids due to toxicity concerns.
General R&D context (non-clinical):
May be used as a coordination ligand to prepare transition‑metal complexes that serve as homogeneous catalysts in fine chemical synthesis, including API intermediate synthesis, within contained research environments.
Given regulatory and EHS constraints around arsenic, modern pharmaceutical process development generally favors alternative ligands (phosphines, NHCs) over arsines.
If used in route scouting, stringent purge and analytical controls (e.g., ICP‑MS for residual As/metal) are essential in accordance with ICH Q3D elemental impurities guidance. This note is general regulatory context and not a claim of suitability.
No therapeutic claims are made. This product is provided strictly for research use only.
Physical Properties
Item-specific specifications
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general reference values (do not construe as specs)
Physical state: Typically a crystalline solid (literature for analogous organoarsines).
Volatility: Low; organoarsines of this size have negligible vapor pressure at ambient temperature (literature).
Solubility profile: Generally soluble in nonpolar to moderately polar organic solvents (toluene, benzene, chlorinated solvents, THF, diethyl ether); practically insoluble in water and highly protic media (literature trend for diarylarsines).
Partitioning: Expected to be strongly hydrophobic (high logP; literature expectation for polyaryl ligands).
Thermal behavior: Many chelating diarylarsines are thermally stable up to >150 °C in inert atmosphere; oxidative degradation may occur in air upon heating (literature).
Discussion and practical notes
Being an As(III) tertiary arsine, the material can slowly oxidize to the corresponding arsine oxide(s) under air, particularly in solution and at elevated temperature. Dry, oxygen‑limited handling helps preserve material integrity (general guidance).
Refractive index, melting point, boiling point, density, UV cutoff, metal impurity profile, water/peroxide content: Not specified for this item; refer to CoA/Spec Sheet.
Quality and Grades
Item-specific quality information
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers: Not specified for this item; refer to CoA/Spec Sheet.
What quality means for this material (general guidance for chelating arsine ligands)
Identity/purity confirmation typically relies on multi-nuclear NMR (1H, 13C; 75As NMR can be informative), HRMS, and elemental analysis (C/H/As). Absence or low levels of arsine oxide impurities is often critical for reproducible metal complexation.
Trace metal content may affect catalysis research. If relevant to your use, request ICP-MS data. For chromatography or photophysical studies, low UV background and absence of fluorescent impurities can matter.
Water and peroxides are not typical specifications for this class; however, dryness and oxygen content of solutions strongly influence stability and performance.
CoA typically provides assay (%), residual solvents, and spectral data. If you require ligand performance metrics (e.g., metal complex formation tests), please contact technical support.
Implications for use
For sensitive coordination studies, pre-dry the ligand (vacuum, ambient temperature) and verify by NMR that no significant oxide is present. For high-precision work, consider in situ titration with a standard metal precursor to benchmark chelation behavior.
Reaction and Applications
This compound is a classic chelating bidentate arsine ligand. Its two soft As(III) donors make it particularly suited for coordination to soft, late transition metals. While modern catalysis favors phosphines or NHCs for many applications, diarylarsines remain valuable in coordination chemistry and in mechanistic or comparative ligand studies.
Coordination chemistry: Forms κ2‑chelate complexes with Pd(II), Pt(II), Ni(II), Rh(I/III), Ir(I/III), Au(I), and Ag(I). The flexible –CH2–CH2– tether affords five‑membered chelate rings and bite angles comparable to dppe (literature: typically ~85–90°, metal‑dependent).
Catalyst precursors: Resulting complexes have been explored in homogeneous hydrogenation, isomerization, and cross‑coupling contexts (literature). Arsine ligands can modulate electron richness and lability differently from phosphines, offering instructive contrasts in reactivity/selectivity.
Soft‑donor preference: Enhanced affinity to soft centers (e.g., Pt(II), Au(I)) can lead to stable, often air‑sensitive complexes with distinctive spectroscopic signatures (e.g., downfield 195Pt shifts in Pt–As systems; literature trend).
Oxidation chemistry: The ligand can be oxidized to the corresponding arsine oxide(s), which alters donor properties (harder As=O). Controlled oxidation can be used to access oxide‑bridged species or to probe ligand effects.
Practical tips: Work under inert atmosphere for complexation. Dry, degassed solvents (DCM, toluene, THF) and Schlenk/glovebox techniques are recommended. Monitor reactions by 1H/13C NMR and, where available, 75As NMR; ESI‑MS is often diagnostic for metal–ligand stoichiometries.
Note: Manufacturer-provided specific applications are not listed for this item; the above are literature/general uses.
Reaction Conditions
General literature guidance for forming metal complexes and using this ligand; not item specifications.
Complexation solvents: DCM, CHCl3, toluene, THF, diethyl ether, or mixtures. Use dry, degassed solvents to minimize oxidation.
Atmosphere: Nitrogen or argon via Schlenk or glovebox techniques. Many As(III) complexes are air‑sensitive.
Temperatures/times: 20–80 °C for 0.5–16 h, depending on metal precursor and ligand exchange kinetics. Lower temperatures often suffice for Au(I)/Ag(I); Pd(II)/Pt(II) may require gentle heating.
Stoichiometry: Common targets include 1:1 chelates [M(L)X2] and 1:2 complexes [M(L)2] for d10/d8 ions; verify by NMR/ESI‑MS.
Bases/additives: Typically unnecessary for neutral chelation; for halide abstraction (to increase coordination), use AgBF4/AgPF6 (caution: light sensitive; produce AgX precipitate).
Workup/isolation: Filter under inert atmosphere, concentrate under reduced pressure, and crystallize by vapor diffusion or layering (e.g., hexanes into DCM). Protect from air and light when needed.
Monitoring: 1H/13C NMR for free ligand vs complexed shifts; IR for M–Cl retention/loss; elemental analysis for bulk purity. 75As NMR (if available) can aid assignment but may be broad.
Yields vary widely with metal/ligand/ancillary ligands (often 50–95% for straightforward substitutions in the literature). Always confirm complex composition by multiple orthogonal methods.
Safety and Handling
Item-specific hazard fields
Signal word / H-statements / GHS classification / Pictograms: Not specified for this item; refer to SDS.
General safety information for organoarsenic compounds (literature; not product-specific)
Toxicology: Trivalent organoarsenicals are considered acutely toxic if ingested, inhaled, or absorbed through skin. Avoid all routes of exposure. Work in a certified chemical fume hood.
PPE: At minimum, wear lab coat, chemical-resistant gloves (e.g., nitrile; change regularly), splash goggles. Consider double‑gloving for extended handling.
Handling: Avoid dust formation. Use inert atmosphere when possible to limit oxidation. Keep away from oxidizers and strong acids. Prevent contact with skin and eyes.
Incompatibilities: Strong oxidants (risk of rapid oxidation to As(V) oxides), halogens, and aggressive electrophiles. Aqueous strongly oxidizing acidic media can generate volatile/toxic arsenic species.
Decomposition/oxidation: Tertiary arsines may form the corresponding arsine oxides on exposure to oxygen; some arsine oxides can be irritant/toxic. Dispose of oxidized residues as arsenic‑containing hazardous waste.
First aid (overview): If inhaled—move to fresh air, seek medical attention. Skin contact—wash with plenty of water and soap, remove contaminated clothing. Eye contact—rinse cautiously for several minutes, seek medical attention. Ingestion—do not induce vomiting; seek immediate medical attention. Provide SDS to responders.
Spills/waste: Avoid aerosolization; collect with damp disposable wipes/adsorbent. Place in sealed container labeled for arsenic waste. Follow institutional and regulatory protocols.
Always consult the product’s SDS for authoritative hazard, exposure limits, and emergency procedures.
Solvent Selection
Polarity and miscibility (literature trends)
Ethylenebis(diphenylarsine) is a hydrophobic, neutral ligand that dissolves well in nonpolar and moderately polar aprotic solvents: toluene, benzene, chlorobenzene, DCM/CHCl3, THF, diethyl ether, and hydrocarbons (with warming). It is poorly soluble in alcohols and essentially insoluble in water.
Selecting solvents for key tasks
Ligand dissolution and complexation: DCM, THF, toluene are common choices due to good solubility and compatibility with typical metal precursors (Pd, Pt, Ni, Rh, Au, Ag).
Crystallization of metal complexes: Slow diffusion of pentane/hexanes into DCM/THF solutions often works well; toluene/ethanol antisolvent pairs can also be effective if the complex tolerates alcohol.
Oxidation sensitivity: Use dry, degassed solvents when preparing solutions for extended periods; arsines can oxidize in oxygenated media.
Comparison (general guidance)
Versus phosphine analogues (e.g., dppe): Solubility behavior is broadly similar; arsine ligands can be slightly more soluble in aromatics due to higher polarizability.
Versus highly polar aprotics (DMF, DMSO): These can dissolve the ligand but may coordinate to metals and compete with ligand binding; choose sparingly for complexation steps.
Note: No UV cutoff, water content, or stabilizer information is specified for this item; consult the CoA/SDS if such parameters are critical for your method.
Storage and Reconstitution
Item-specific storage
Storage conditions: Room temperature (per Product Data).
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
General handling and solution preparation (literature guidance)
Container: Store tightly closed in an inert, dry environment. Although room temperature is indicated, many laboratories keep tertiary arsines under inert gas (N2/Ar) and protected from light to minimize slow oxidation—especially for opened containers and solutions.
Solid handling: Minimize air exposure; promptly recap under N2. If needed, gently dry under vacuum at ambient temperature before critical experiments.
Preparing stock solutions: Use dry, degassed solvents (e.g., DCM, toluene, THF). Prepare only what is needed for near‑term use. Filter through PTFE syringe filters to remove particulates.
Solution stability: Arsine solutions can oxidize over days at ambient conditions; store under N2/Ar at 2–8 °C in amber vials if long‑term storage is necessary. Discard if precipitation, discoloration, or new NMR signals (arsine oxide) appear.
Freeze–thaw: Not generally applicable for solids; avoid repeated freeze–thaw of solutions—prepare fresh instead.
For any missing item-specific parameters (appearance, purity, stabilizers, shelf life), consult the CoA/Spec Sheet. Always label containers clearly: “For research use only.”
Structure and Identity
Item-specific (from Product Data)
Product name: Ethylenebis(diphenylarsine)
CAS: 4431-24-7
PubChem CID: 20488
InChIKey: 290876 (as provided)
Storage: Room temperature
Research use: For research use only
Literature/Computed identifiers and structural description (for reference; not item specifications)
Idealized 2D structure (description): An ethylene linker –CH2–CH2– connects two trivalent arsine centers. Each As(III) bears two phenyl rings [–As(Ph)2], giving a symmetric, chelating bidentate ligand of the type (C6H5)2As–CH2–CH2–As(C6H5)2.
Key functional groups/features: Two soft donor tertiary arsine centers (AsIII), four phenyl rings per As center (total eight phenyl rings in the molecule), flexible –CH2–CH2– tether enabling κ2‑chelation to transition metals.
Stereochemistry: Overall achiral in the free ligand; metal coordination may generate diastereomeric chelates depending on the complex.
Notes
SMILES and full standardized InChIKey are not specified for this item; refer to CoA/Spec Sheet. Public databases (e.g., PubChem CID 20488) list canonical line notations for reference only.
The molecule is the arsenic analogue of the well-known diphosphine dppe, with longer As–C bonds and softer donor character, typically favoring softer, late transition metals.
Synthetic Utility
As a bidentate soft donor ligand, Ethylenebis(diphenylarsine) offers several synthetic advantages in coordination and organometallic chemistry.
Chelation and geometry control: The –CH2–CH2– tether furnishes a five‑membered chelate, enforcing cis‑chelation on square‑planar d8 metals (PdII, PtII) and stabilizing 16‑ or 18‑electron complexes (literature). The softer As donors modulate electron density differently from P analogues.
Ligand effects: Relative to diphosphines, arsines can yield more labile metal–ligand interactions in some systems, impacting oxidative addition/reductive elimination kinetics. This can be probed in cross‑coupling or isomerization model reactions.
Building block for complexes: Straightforward ligand substitution on MCl2(PR3)2 or M(acac)2 precursors in DCM/THF provides [MCl2(L)] or [M(L)2] motifs (M = Pd, Pt, Ni, etc.), often isolable by crystallization.
Transformations on the ligand: Electrophilic aromatic substitution on the phenyl rings (e.g., nitration, halogenation) enables second‑sphere tuning of sterics/electronics. Controlled oxidation to arsine oxide(s) can generate harder donor variants for comparative studies.
Spectroscopic handles: 1H/13C NMR are diagnostic; 75As NMR (if available) provides sensitive probes of coordination environment, albeit with broader lines compared to 31P.
These capabilities make the ligand a useful tool for structure–reactivity exploration and for benchmarking against dppe/dppp in catalytic screening.
Target Specificity
Not applicable. This product is a small-molecule organoarsenic ligand, not a biological targeting reagent or antibody. No antigen/epitope, clone, isotype, or species reactivity information pertains to this item.
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