Chlorure de tétraphénylarsonium monohydraté - ≥99% , CAS No.104170-16-3

CAS: 104170-16-3 Cat. No.: T282562 Formule: C₂₄H₂0AsCl Poids moléculaire: 418.80 (436.81) PubChem CID: 2723786

GRADE & PURITY ≥99%

Synonyms

Tetraphenylarsonium chloride monohydrate | FT-0642558 | Tetraphenylarsonium(V) chloride hydrate, 97% | DTXSID20369101 | Arsonium, tetraphenyl-,chloride, hydrate (1:1:1) | SCHEMBL3469001 | MFCD00149995 | tetraphenylarsanium;chloride;hydrate | Tetraphenylar

Storage

Room temperature

Specifications

Synonymes

Tetraphenylarsonium chloride monohydrate | FT-0642558 | Tetraphenylarsonium(V) chloride hydrate, 97% | DTXSID20369101 | Arsonium, tetraphenyl-,chloride, hydrate (1:1:1) | SCHEMBL3469001 | MFCD00149995 | tetraphenylarsanium;chloride;hydrate | Tetraphenylar

Spécifications et pureté

≥99%

Conditions de stockage de stockage

Room temperature

Pureté

≥99%

Noms et identifiants

Sourires canoniques

C1=CC=C(C=C1)[As+](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4.O.[Cl-]

IUPAC Name

tetraphenylarsanium;chloride;hydrate

InChIKey

NGDWSDTZKCSLRK-UHFFFAOYSA-M

INCHI

1S/C24H20As.ClH.H2O/c1-5-13-21(14-6-1)25(22-15-7-2-8-16-22,23-17-9-3-10-18-23)24-19-11-4-12-20-24;;/h1-20H;1H;1H2/q+1;;/p-1

Isomères SMILES

C1=CC=C(C=C1)[As+](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4.O.[Cl-]

PubChem CID

2723786

Poids moléculaire

418.80 (436.81)

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Benzene and substituted derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzene and substituted derivatives
• Alternative Parents: Tetraorganoarsonium salts Oxygen-containing organoarsenic compounds Organic metalloid salts Organopnictogen compounds Organic oxides Organic chloride salts Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Tetraorganoarsonium salt - Monocyclic benzene moiety - Oxygen-containing organoarsenic compound - Organic metalloid salt - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organic chloride salt - Organic salt - Organoarsenic compound - Aromatic homomonocyclic compound
• Description: 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.
• External Descriptors: Not available

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Propriétés chimiques et physiques

• Point de fusion (°C): 257°C
• Poids moléculaire: 436.800 g/mol
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 436.058 Da
• Monoisotopic Mass: 436.058 Da
• Topological Polar Surface Area: 1.000 Ų
• Heavy Atom Count: 27
• Formal Charge: 0
• Complexity: 301.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 3

XLogP3

Application Protocols

No assay-specific or bioanalytical application protocols are provided for this item in the Product Data. For general synthetic use as a counterion/ion-pairing reagent, consider the following generic workflow (literature/general):

• Ion-pair precipitation (generic):
  1. Dissolve the anionic substrate (as its alkali-metal salt) in minimal MeOH/MeCN.
  2. Prepare an equimolar solution of tetraphenylarsonium chloride monohydrate in the same solvent.
  3. Combine slowly with stirring; monitor for precipitation of [AsPh4][X].
  4. Allow to age 0.5–2 h, then filter, wash, and dry.
• Crystallization for structure determination:
  1. Dissolve crude [AsPh4][X] in CH2Cl2 or MeCN to clarity (optionally hot-filter).
  2. Layer with Et2O or hexanes; cap loosely to allow slow diffusion.
  3. Grow crystals over 1–3 days; harvest under inert atmosphere if the anion is air/moisture sensitive.

These are starting points; optimize solvent, temperature, and concentration for your specific anion and desired solid-state form. Always consult primary literature if your system is known to form polymorphs or solvates.

Biological Roles

This product is not intended for biological or clinical use. No biological roles are specified for this item.

General information (literature/general):

• Quaternary arsonium salts lack natural biological roles and are synthetic constructs. The tetraphenyl-substituted arsonium cation is bulky and lipophilic, which may enable membrane interaction, but its arsenic content and ionic nature preclude intentional biological application.
• Compared with triphenylphosphonium cations (used as mitochondrial-targeting vectors in research), tetraphenylarsonium has limited precedence in bio-conjugation due to safety/toxicity concerns and the absence of reactive handles.
• Enzymatic pathways for organoarsenic compounds in biology are niche and not typically relevant to tetraphenylarsonium salts. Environmental and microbial arsenic transformations focus on inorganic/mono- or dimethylated arsenicals, not tetraaryl arsonium cations.

If any biochemistry-related study is contemplated (e.g., ion-pairing extraction from biological matrices), ensure containment, assess toxicity, and strictly adhere to institutional safety protocols. For detailed toxicological data and exposure limits, consult the SDS and primary literature.

Research use note: For research use only (product data). No medical, diagnostic, or therapeutic use is intended.

Buffer Applications

Not typically applicable. Tetraphenylarsonium chloride monohydrate is not a buffering agent and is not used to prepare pH buffer systems. If used in aqueous systems, it is typically as an ion-pairing or counterion reagent at low concentrations rather than for pH control.

For pH control in the laboratory, choose dedicated buffering systems (e.g., phosphate, HEPES, Tris) appropriate to your pH and ionic strength needs.

Green Alternatives

Given the presence of arsenic, tetraphenylarsonium salts pose environmental and health concerns. When feasible, consider alternative countercations with lower inherent hazard while retaining similar physicochemical behavior.

Comparison of counterions (literature/general):

• Tetraphenylphosphonium (TPP+):
  • Pros: Similar size/lipophilicity; widely available; generally considered less acutely toxic than arsenic analogs; extensive precedent in anion isolation and phase-transfer applications.
  • Cons: Still not “green”; P-based salts can be persistent; some TPP salts are hygroscopic.
• Tetraalkylammonium (e.g., NBu4+):
  • Pros: Broad availability; good solubility tuning via alkyl chain; often cheaper.
  • Cons: More flexible/less rigid than aryl onium; sometimes gives oils rather than crystalline solids; can be more hygroscopic; may coordinate weakly in some systems.
• Imidazolium/triazolium ionic liquids:
  • Pros: Tailorable cations; potential for recyclable media; can enhance solubility in organic phases.
  • Cons: May be harder to crystallize discrete salts; thermal stability and viscosity issues.

Trade-offs:

• Crystallographic quality: Tetraphenyl cations (P/As) often yield superior single crystals compared with tetraalkylammonium.
• Toxicology/regulatory: Replacing As with P or N reduces regulatory burden and potential environmental impact.
• Waste minimization: Use the minimum stoichiometric excess of onium salt; recover and recycle counterions where possible (e.g., convert back to chloride and reuse).

Recommendation: Where the unique crystallization behavior of [AsPh4]+ is not essential, substitute with tetraphenylphosphonium or tetra-n-butylammonium analogs to reduce hazard while maintaining functionality.

Pharmaceutical Uses

No pharmaceutical or excipient use is specified for this item. Due to the presence of arsenic, tetraphenylarsonium salts are generally unsuitable for pharmaceutical formulation.

General context (literature/general):

• Quaternary onium salts such as tetraphenylphosphonium or tetraalkylammonium derivatives can serve specialized roles in analytical sample preparation or as phase-transfer catalysts in process chemistry. However, arsonium analogs are rarely, if ever, selected for pharmaceutical processes because of toxicological concerns and regulatory hurdles associated with arsenic-containing materials.
• If a lipophilic countercation is required for a process-screening exercise, safer surrogates (e.g., tetraphenylphosphonium, tetrabutylammonium) should be preferred.

This product is supplied strictly for research use only (product data) and is not intended for use in humans or animals.

Physical Properties

Item-specific specifications are not provided in the Product Data. The following are literature/general characteristics for tetraphenylarsonium chloride and closely related hydrates; do not treat as product specifications.

• Physical state/appearance: Typically a crystalline, high-melting ionic solid (literature/general). Color is typically white to off-white (literature/general).
• Melting behavior: Reported as a high-melting solid that may soften or decompose on heating; anhydrous tetraphenylphosphonium chloride melts ~277–279 °C; arsonium analogs are similar and may decompose before clear melt (literature/analogy; exact MP for this hydrate not specified).
• Solubility profile (qualitative, literature/general):
  • Sparingly soluble to moderately soluble in water (hydrate may improve wetting but ion pairing reduces aqueous solubility).
  • Soluble in polar organic solvents including acetonitrile, acetone, alcohols (MeOH/EtOH), and chlorinated solvents; poor solubility in nonpolar alkanes.
• Partitioning: The lipophilic arsonium cation imparts significant affinity for organic phases (qualitative, literature/general).
• Density, refractive index, pKa, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet or SDS.

Practical notes (general):

• Crystallinity and hydrate state can influence solubility and thermal behavior; gentle drying under vacuum at ambient temperature is preferred if moisture content must be reduced without altering hydrate state.
• For precise values (mp, solubility in specific solvents, water content), consult the lot-specific CoA.

Quality and Grades

• Grade/purity: Not specified for this item; refer to CoA/Spec Sheet for the lot-specific assay, inorganic impurities, and water content.
• What “grade” typically means (general guidance):
  • Research or reagent grade indicates suitability for most synthetic and analytical laboratory operations.
  • Where applicable, “high-purity” salts for ion-pairing/crystallization are characterized by low halide variability, low metal contamination, and controlled hydrate/solvent content to ensure reproducible crystallization behavior.
• Counterion and hydrate control (general): The defined chloride counterion and monohydrate stoichiometry are important for reproducibility in anion metathesis, precipitation yields, and X-ray quality crystals. If the precise hydration state matters, confirm by TGA/Karl Fischer as noted on the CoA.
• Stabilizers/inhibitors: None are typically used for quaternary arsonium salts; if any stabilizer is present, it will appear on the CoA. Not specified for this item.
• UV profile/LC suitability: If using as an ion-pairing reagent for LC separations or salt metathesis prior to spectroscopic measurements, consider grade requirements such as low UV background and low residual ionic contaminants (general advice). Consult the CoA for UV absorbance (if provided) and residual metals/halides.
• Documentation: For method validation or regulated work, retain CoA, SDS, and any available specification sheet. Request additional QA documentation if needed (e.g., ICP-MS metals, halide assay, KF moisture).

Reaction and Applications

Although not a reagent in the classical sense, tetraphenylarsonium chloride monohydrate is widely used as a counterion source and ion-pairing agent.

Key applications (literature/general):

• Anion metathesis and isolation:
  • Exchange chloride for target anions (e.g., tetrahalometallates, polyoxometalates, pseudohalides) to form [AsPh4][X] salts, which are often less hydrated and more crystallizable than alkali-metal salts.
  • Facilitates purification of sensitive anions by separating them from coordinating cations (Na+, K+), improving NMR/IR interpretation and enabling single-crystal X-ray diffraction.
• Ion-pairing in separations: Used as an ion-pairing agent in nonaqueous or mixed-solvent chromatography/electrophoresis for highly charged anions (less common today due to toxicity considerations; literature/general).
• Phase-transfer and reactivity modulation: The large lipophilic arsonium cation can solubilize otherwise insoluble inorganic anions in organic media, enabling reactions under biphasic or nonaqueous conditions (general concept).

Practical tips:

• Perform salt metathesis in MeOH/EtOH or MeCN by mixing equimolar solutions of [AsPh4]Cl·H2O and a metal salt containing the desired anion; precipitated salts can often be collected by filtration and washed with cold solvent or ether.
• If halide-free conditions are required, pre-exchange chloride with a weakly coordinating anion (e.g., BF4−, PF6−) before introducing highly halide-sensitive substrates.
• Avoid strong nucleophiles/bases that could attack aryl-As bonds (rare but possible under forcing conditions); under typical conditions the arsonium cation is inert.

Note: For this specific catalog item, no special application testing is provided; consult primary literature for your anion system.

Reaction Conditions

The following general conditions apply to the use of tetraphenylarsonium chloride monohydrate in salt metathesis and crystallization workflows (literature/general guidance; optimize for your specific system):

• Salt metathesis to form [AsPh4][X]:
  • Solvent: Methanol, ethanol, or acetonitrile commonly dissolve both partners. If solubility of the product is low, precipitation occurs directly.
  • Stoichiometry: 1:1 equivalents of [AsPh4]Cl·H2O and a soluble source of anion X− (e.g., NaX, HX neutralized in situ). For oxygen-sensitive anions, use rigorously dried, degassed solvents.
  • Temperature: 20–60 °C to enhance dissolution; avoid prolonged heating to prevent hydrate loss or decomposition.
  • Workup: Filter precipitate, wash with cold solvent and then a non-solvent (Et2O, hexanes) to remove adhering mother liquor; dry under vacuum at ambient temperature.
• Crystallization for X-ray diffraction:
  • Prepare a clear solution in CH2Cl2 or MeCN, then layer with Et2O or hexanes, or use vapor diffusion. Slow evaporation at room temperature often yields well-formed crystals over 12–72 h.
  • Seed if necessary; maintain constant temperature and minimize vibrations.
• Analytical characterization:
  • Confirm anion incorporation and stoichiometry by elemental analysis, 1H NMR (aromatic signals of AsPh4+), and, where applicable, 13C NMR and MS of the anion. TGA/KF to verify hydrate content.

Expected outcomes: Yields are often high (literature reports frequently >70% for straightforward metatheses), but crystallinity and polymorphism depend on solvent, temperature, and hydrate state.

Safety and Handling

Hazard classification for this specific item is not provided in the Product Data. Always consult the SDS for authoritative guidance.

• GHS/CLP: Not specified for this item; refer to SDS. Arsenic-containing compounds are often harmful or toxic; handle with heightened caution (general guidance).
• Likely hazards (general for arsonium salts): Toxic if swallowed or inhaled; may cause skin/eye irritation. Avoid dust formation and aerosolization. Environmental persistence/toxicity to aquatic life is possible for arsenic-containing materials.
• PPE: Laboratory coat, safety goggles, and chemically resistant gloves (e.g., nitrile). Use a fume hood to avoid inhalation of dust.
• Handling: Minimize dust; avoid ingestion, inhalation, and skin/eye contact. Do not pipette by mouth. Keep away from strong oxidizers and strong bases/acids that could alter the ion pair or promote decomposition (general).
• First aid (general):
  • Inhalation: Move to fresh air; seek medical attention; provide oxygen if needed.
  • Skin: Remove contaminated clothing; wash with soap and water.
  • Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present; seek medical advice.
  • Ingestion: Rinse mouth; do not induce vomiting; seek immediate medical attention.
• Spills: Avoid breathing dust. Sweep up carefully and place in suitable container for disposal. Decontaminate area. Prevent entry into waterways.
• Waste disposal: Treat as hazardous waste; dispose via licensed chemical waste contractor in accordance with local regulations for arsenic-containing substances.
• Storage: Room temperature (product data). Keep tightly closed in a dry, well-ventilated place; protect from moisture to maintain defined hydrate state.

Note: This product is for research use only (product data).

Solvent Selection

Tetraphenylarsonium chloride monohydrate is an ionic solid with a bulky, lipophilic cation. Solvent choice is driven by desired ion-pairing, solubility, and crystallization outcomes.

• Polarity/miscibility (literature/general):
  • Better solubility in polar aprotic organics (acetonitrile, nitromethane, DMF, DMSO) and in polar protic alcohols (MeOH, EtOH) than in nonpolar hydrocarbons.
  • Limited water solubility; hydrate state can marginally improve wetting but not necessarily bulk solubility.
• Typical use scenarios:
  • Anion metathesis/precipitation: Dissolve the arsonium salt and target anion source in a mutual solvent (e.g., MeOH, EtOH, MeCN) and then adjust solvent polarity to precipitate the desired arsonium-anion salt.
  • Crystallization for X-ray: Use acetonitrile or dichloromethane/Et2O vapor diffusion; slow diffusion of a nonsolvent (Et2O, hexanes) into a solution in MeCN/CH2Cl2 often yields good crystals (general practice).
• Comparison (general):
  • vs. Water: Poor solubility limits utility for purely aqueous ion-pairing.
  • vs. Alcohols (MeOH/EtOH): Good compromise for metathesis and easy solvent removal; may co-crystallize solvent.
  • vs. MeCN/CH2Cl2: Excellent for preparing X-ray quality single crystals by vapor diffusion or layering.
• Practical tips:
  • Filter hot solutions to remove insolubles; allow slow cooling for better crystallinity.
  • Maintain consistent hydrate state; prolonged drying at elevated temperature may alter water content and affect crystallization behavior.
• Data gaps: Dielectric constant, partition coefficients, and quantitative solubilities are not specified for this item; consult literature or perform small-scale tests.

Storage and Reconstitution

• Storage conditions: Room temperature (product data). Store in a tightly closed container in a dry, well-ventilated place. Protect from moisture to maintain the defined monohydrate state.
• Handling of hydrate state: If your application requires a specific water content, verify by Karl Fischer or TGA. Avoid drying at elevated temperatures that could alter the hydrate stoichiometry.
• Reconstitution/dissolution (general guidance):
  • For metathesis operations, dissolve in methanol, ethanol, or acetonitrile with gentle warming and stirring. If insoluble components persist, hot-filter through a pre-warmed frit.
  • For crystallization, prepare clear solutions in CH2Cl2 or MeCN and use vapor diffusion with ether or hexanes.
• Freeze–thaw: Not applicable; store as a solid. If solutions are prepared, store refrigerated and protected from moisture; prepare fresh when possible to avoid changes in hydrate/solvate content.
• Shipping: Not specified for this item; refer to CoA/Spec Sheet. Typically ships at ambient temperature for stable ionic solids.
• Shelf life: Not specified; assess by periodic inspection for discoloration or changes in solubility/crystallinity, and confirm by analytical methods as needed.

Note: For research use only (product data). Always defer to the lot-specific CoA and SDS for definitive storage and handling instructions.

Structure and Identity

Tetraphenylarsonium chloride monohydrate is a lipophilic quaternary arsonium salt, useful as a non-coordinating countercation for isolating and crystallizing anionic complexes.

• SKU: T282562
• Product name: Tetraphenylarsonium chloride monohydrate
• CAS: 104170-16-3 (product data)
• PubChem CID: 2723786 (product data)
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: As+(c2ccccc2)(c3ccccc3)c4ccccc4.[Cl-].O (literature depiction; cation/anions plus one water of crystallization)
• Structural features (general description):
  • Central tetracoordinate arsenic atom formally cationic (AsV in arsonium form) bonded to four phenyl rings, giving a bulky, highly delocalized, lipophilic cation [As(C6H5)4]+.
  • Counterion: chloride (Cl−); monohydrate indicates one lattice water per formula unit.
  • 2D structure (in words): a tetrahedral As center substituted by four phenyl rings; the chloride anion and one water molecule are not covalently bound to the cation but present in the crystal lattice.
• Molecular formula: C24H22AsClO (monohydrate; derived from the name, literature/computed)
• Molecular weight: ~436.81 g/mol (computed from C24H22AsClO; literature/computed)

Notes: Item-specific identifiers (exact stereochemistry not applicable; quaternary arsonium has no stereogenic center here). For authoritative identifiers and release specifications, consult the CoA for this lot.

Synthetic Utility

Tetraphenylarsonium chloride monohydrate is primarily valuable as a source of the [AsPh4]+ counterion rather than as a reagent undergoing transformation.

Utility in synthesis (literature/general):

• Counterion exchange and isolation:
  • Enables preparation of discrete salts [AsPh4][X] for a wide variety of anions (e.g., metal halide complexes, pseudohalides, oxoanions), improving crystallinity and facilitating characterization (NMR, IR, elemental analysis, and single-crystal XRD).
• Reaction medium modification:
  • Increases solubility of polar anions in organic solvents, enabling homogeneous reactions or extractions in nonaqueous media.
• Retrosynthetic value:
  • When designing isolation of a sensitive or reactive anion, replacing small, coordinating cations (Na+, K+) with a weakly coordinating, bulky onium cation can stabilize the anion and reduce ion pairing with the solvent or counterion, aiding both structure elucidation and downstream reactivity mapping.
• Stability/compatibility:
  • The arsonium cation is generally inert under neutral conditions; avoid strongly basic/nucleophilic environments that can cleave aryl–As bonds under forcing conditions.

Alternatives and orthogonality:

• Consider tetraphenylphosphonium or tetra-n-butylammonium salts when arsenic handling is restricted. These alternatives often deliver comparable ion-pairing and crystallization behavior with lower toxicological burden.

Target Specificity

Not applicable. This product is a small-molecule salt (inorganic/organometallic reagent), not a biological targeting reagent, antibody, or probe. No antigen, clone, isotype, or species reactivity applies.