This compound belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
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.
Certificados (CoA, COO, BSE/TSE y tabla de análisis)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propiedades químicas y físicas
Peso molecular
356.580 g/mol
XLogP3
4.500
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
3
Exact Mass
355.946 Da
Monoisotopic Mass
355.946 Da
Topological Polar Surface Area
17.100 Ų
Heavy Atom Count
17
Formal Charge
0
Complexity
261.000
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
1
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Application Protocols
Not applicable. This product is not validated for bioassays such as WB, IHC, IF, or flow cytometry, and no protocols or dilutions are specified. For synthetic applications, refer to the Reaction & Applications and Reaction Conditions sections for literature-style guidance, and adapt to your specific transformation.
Biological Roles
This product is a synthetic, halogenated aryl ketone intended for chemical research. It is not a metabolite, cofactor, or known biomacromolecular ligand with a defined biological role.
General context (not specific to this item):
Aryl ketones can interact with biological membranes due to hydrophobicity and may show UV absorption, but such properties are incidental and highly structure-dependent.
Halogenated aromatics (especially iodides) can participate in halogen bonding in protein–ligand interactions, which is a rationale for their use as synthetic intermediates toward bioactive molecules. However, this compound itself is supplied strictly for research and synthetic use.
No biological pathway, receptor specificity, or cellular function is assigned to this product. Any evaluation of bioactivity should be conducted under appropriate laboratory approvals and is outside the scope of catalog documentation. For all safety, toxicology, and environmental fate information, refer to the SDS and consult primary literature for structurally related compounds if needed.
Buffer Applications
Not typically applicable. This compound is a non-ionic, hydrophobic organic building block, not a buffering reagent. It does not form defined acid–base conjugate pairs in water suitable for pH control.
Practical note: If used in aqueous biochemistry experiments as a small-molecule probe or substrate precursor, it will generally be dissolved first in a water-miscible organic co-solvent (e.g., DMSO, MeCN) before dilution into buffers. Verify solubility and avoid precipitates; final organic content is commonly kept ≤1–2% v/v for biochemical assays unless otherwise justified.
Green Alternatives
Opportunities to improve the environmental profile when working with halogenated aryl ketones/aryl iodides focus on solvent choice, coupling partners, and oxidants/reductants rather than on the substrate itself (which is fixed by design).
Greener substitutions (general guidance):
Solvents: replace dichloromethane/DMF where possible with 2‑MeTHF, CPME, EtOAc, MeOH, or water/dioxane mixtures. For Suzuki couplings, 2‑MeTHF–H2O or EtOH–H2O often perform comparably to dioxane–H2O.
Bases: use K3PO4, K2CO3, or Na2CO3 in aqueous/biobased solvents instead of strong organic bases in high-boiling dipolar aprotics.
Catalysts: employ ligand-efficient Pd catalysts at ppm–0.1 mol% loadings or explore Ni catalysis where compatible; consider supported catalysts for easier recovery.
Oxidations: for Baeyer–Villiger or related oxidations, consider Oxone, hydrogen peroxide with organocatalysts, or biocatalytic BV monooxygenases in place of mCPBA, balancing selectivity and safety.
Reductions: swap tin hydrides or Zn/HCl with catalytic hydrogenation or transfer hydrogenation (isopropanol, formate) when feasible.
Comparison snapshot (illustrative; not item-specific):
DCM vs EtOAc: EtOAc offers lower toxicity and renewable sourcing, with similar extraction/chromatography performance.
DMF vs 2‑MeTHF: 2‑MeTHF is bio-derived, lower toxicity, and easier to remove; ensure solubility and base compatibility.
mCPBA vs H2O2: H2O2 generates benign byproducts (water) but may require catalysts and careful control for selectivity.
Tradeoffs should be validated at small scale; monitor reaction rates, selectivity, and impurity profiles upon process changes.
Pharmaceutical Uses
No excipient or pharmacopeial status is specified for this item; it is supplied for research use only.
General context (not a claim for this item):
Halogenated aryl ketones and aryl iodides are frequent intermediates in medicinal chemistry campaigns. The aryl iodide serves as a versatile handle for late-stage diversification via Pd/Ni-catalyzed cross-coupling to access SAR arrays. The ketone can be elaborated to alcohols, imines, oximes, or heterocycles (e.g., oxazoles) that appear in candidate libraries.
In process development, selection of the iodide vs bromide/chloride is often a balance of reactivity and cost; iodides enable milder conditions but can be less stable to metalation and more expensive. Protect from light and use controlled temperatures to maintain product quality.
This product is not intended for human or veterinary use, diagnostic procedures, or as an API. Any application in pharmaceutical R&D should be confined to synthetic intermediate roles under appropriate GMP or research-quality controls as required by the project stage.
Physical Properties
Item-specific specifications (this lot):
Melting point, boiling point, density, refractive index, solubility, logP, pKa, UV cutoff, water/impurity limits: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general expectations for halogenated aryl ketones (contextual, not item specs):
Many diaryl/aryl ketones with heavy halogens are crystalline solids at ambient temperature, exhibiting relatively high melting points and low vapor pressures due to increased molecular weight and polarizability.
Solubility profile is typically: good solubility in moderately polar aprotic organic solvents (e.g., dichloromethane, chloroform, ethyl acetate, acetone, acetonitrile, DMF, DMSO) and poor solubility in water. Actual solubility must be verified experimentally for this specific item.
Aryl iodides generally have higher refractive indices and greater UV absorption in the near-UV region than their lighter analogs; for chromatographic work, low-UV solvents are often preferred.
Practical notes (general):
If the compound is solid, gentle warming (≤40–50 °C) and sonication can aid dissolution in organic solvents; avoid prolonged heating to prevent decomposition of the C–I bond.
For analytical characterization, 1H/13C NMR in CDCl3 or DMSO‑d6, HRMS (ESI/APCI), and HPLC/UPLC (reverse phase) are commonly suitable for aryl ketones and aryl iodides. TLC visualization may benefit from UV and halogen-sensitive stains (e.g., phosphomolybdic acid).
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and guidance:
When grade is unspecified, Aladdin Scientific supplies research-grade material suitable for synthetic and analytical R&D. For sensitive applications (e.g., catalysis screening, materials research), consult the CoA for assay, related substances, and residual solvent data specific to the lot you receive.
If HPLC/GC assay is reported on the CoA, it typically reflects area% purity under stated analytical conditions. Trace metals and halide content are not controlled unless explicitly specified.
UV-Vis background and fluorescence: for aryl ketones and aryl iodides, low-UV/purity grades (HPLC/LCMS grade) matter primarily for solvents rather than solutes; however, if you require minimized UV background, request spectral scans or perform your own baseline checks in your measurement solvent.
Stabilizers/inhibitors: None are listed for this item. If a stabilizer is present for your lot, it will be disclosed on the CoA/label. Aryl iodides generally do not require polymerization inhibitors, but they can benefit from amber packaging to limit photolysis.
Batch-to-batch reproducibility: expect consistent appearance and assay within normal manufacturing tolerances; for process-critical uses, qualify the material with a retained sample and reference method. Contact technical support for additional documentation (CoA, SDS, TDS) or pre-shipment lot confirmation.
Reaction and Applications
This compound is a multifunctional aryl ketone bearing both an aryl iodide (highly reactive C–I bond) and an aryl chloride plus a carbonyl group. Such scaffolds are valuable bifunctional building blocks for divergent synthesis. Typical research applications include:
Cross-coupling at Ar–I: The aryl iodide undergoes rapid oxidative addition, enabling Suzuki–Miyaura (to install aryl/heteroaryl/alkenyl groups from boron partners), Sonogashira (terminal alkynes), Heck (olefins), Negishi (organozincs), and Stille (organostannanes). Catalysts: Pd(PPh3)4, Pd2(dba)3/XPhos/SPhos, or modern precatalysts. The remaining aryl chloride can be addressed subsequently under more forcing conditions, enabling sequential, chemoselective couplings.
Nucleophilic aromatic substitution or Buchwald–Hartwig amination on the chloro-aryl (after or before coupling at Ar–I), allowing introduction of amines or oxygen nucleophiles where the ring electronics permit.
Carbonyl transformations: formation of oximes/semicarbazones (analytical or synthetic), reduction to benzylic alcohols (NaBH4, catalytic hydrogenation), or Baeyer–Villiger oxidation to aryl esters/phenyl acetates (peracids). Enolate chemistry (α-alkylation/acylation) is feasible for acetophenone-like motifs.
Halogen–lithium exchange at Ar–I (e.g., with s-BuLi at low temperature) to access aryllithiums for directed functionalization, then quench with electrophiles (CO2, DMF, B(OMe)3, etc.).
Photoredox and radical methodologies: aryl iodides are excellent precursors to aryl radicals under photocatalysis or EDA conditions, enabling C–C and C–X bond formations.
These complementary handles support iterative, orthogonal diversification en route to ligands, materials precursors, and heteroaromatic arrays.
Reaction Conditions
The following are general literature-style conditions for aryl iodides and aryl ketones of comparable structure. They are provided as guidance only and are not specifications for this item.
Suzuki–Miyaura coupling (Ar–I): Pd(PPh3)4 (1–2 mol%), K2CO3 or K3PO4 (2–3 equiv), dioxane/H2O (3:1), 60–90 °C, 2–12 h. Ligand-accelerated systems (XPhos/SPhos) enable lower loadings and milder temperatures; aqueous EtOH or 2‑MeTHF/H2O often works well.
Buchwald–Hartwig amination (at Ar–Cl, post-I coupling): Pd2(dba)3 (1–2 mol%) + BrettPhos or XPhos (2–4 mol%), NaOtBu or Cs2CO3, toluene or dioxane, 90–120 °C, 6–18 h. Nickel catalysts (e.g., Ni(cod)2/dppp) are alternatives.
Sonogashira (Ar–I): Pd(PPh3)2Cl2 (1–2 mol%), CuI (2–5 mol%), Et3N or i‑Pr2NH, THF/Et3N or DMF, rt–60 °C, 2–8 h. Copper-free variants reduce Glaser homocoupling.
Heck (Ar–I): Pd(OAc)2 (1–2 mol%) with PPh3 or Pd(PtBu3)2, NEt3 or K2CO3, DMF/dioxane, 80–120 °C, 4–16 h.
Baeyer–Villiger oxidation of aryl ketone: mCPBA (1.5–2.0 equiv) in DCM, 0–25 °C, 2–12 h; or H2O2 (30%) with catalyst (e.g., trifluoroacetone or Sn-catalyzed) in MeCN/AcOH, 25–50 °C. Monitor for over-oxidation.
Carbonyl reduction: NaBH4 (1.5–3 equiv) in MeOH/EtOH at 0–25 °C; catalytic hydrogenation (Pd/C, H2) in EtOAc/MeOH at ambient to 50 °C.
Halogen–lithium exchange: s‑BuLi (1.1–1.5 equiv) in THF at −78 to −40 °C, 5–30 min, then electrophile quench (e.g., DMF, CO2). Exercise strict cryogenic technique.
Always degas solvents for cross-coupling, dry glassware, and confirm compatibility of bases/solvents with the substrate to prevent undesired dehalogenation or ketone condensation.
Safety and Handling
Item-specific hazard information:
Signal word, H-statements, GHS classification, pictograms: Not specified for this item; refer to SDS.
General safety guidance for halogenated aryl ketones and aryl iodides (informational; consult the SDS for authoritative data):
Potential hazards: may cause skin/eye irritation; dusts or vapors (if heated) may cause respiratory irritation. Aryl iodides can undergo light/heat-induced decomposition producing iodine-containing irritants.
PPE: wear lab coat, safety goggles, and suitable chemical-resistant gloves (e.g., nitrile). Use in a chemical fume hood to avoid inhalation of dust or vapors.
Incompatibilities: avoid strong bases with prolonged heating (possible elimination/substitution), strong reducing agents (risk of dehalogenation), and strong oxidizers. Protect the aryl iodide moiety from excessive light and heat to minimize homolysis. Avoid sodium metal/alkali metals and highly nucleophilic organometallics unless intended.
First aid overview: on skin contact, wash with soap and water; for eye contact, flush with water for at least 15 minutes and seek medical attention; if inhaled, move to fresh air and obtain medical advice; if ingested, rinse mouth and seek medical attention. Do not induce vomiting unless directed by medical personnel.
Fire and thermal decomposition: use CO2, dry chemical, or foam. Combustion may produce CO/CO2 and hydrogen halides. Firefighters should wear self-contained breathing apparatus.
Waste: collect halogenated organic waste separately in appropriate containers; follow institutional and local regulations.
Solvent Selection
Item-specific solubility data: Not specified for this item; refer to CoA/Spec Sheet.
General solvent guidance for halogenated aryl ketones/aryl iodides:
Polarity class: moderately nonpolar to weakly polar organic solute; typically well-soluble in chlorinated solvents (dichloromethane, chloroform), aromatic hydrocarbons (toluene), and polar aprotics (THF, acetone, acetonitrile, DMF, DMSO). Poorly soluble in water.
Reaction media: for cross-coupling at Ar–I, common solvents include toluene, dioxane, DMF/DMAc, or mixed dioxane–water; for carbonyl transformations (oxime formation, Baeyer–Villiger), choose dichloromethane, MeCN, or greener options like ethyl acetate/2-MeTHF where compatible.
Workup and purification: ethyl acetate/hexanes or dichloromethane/hexanes systems often provide good chromatographic separations for halogenated aryl ketones. Consider reverse-phase preparative HPLC (MeCN/H2O + 0.1% acid) if normal-phase fails.
Moisture/O2 sensitivity: generally air-stable; however, for metal-catalyzed couplings, rigorously dry, degassed solvents are recommended. Aryl iodides are susceptible to light-promoted homolysis; use amber glassware/foil when prolonged exposure is expected.
Quick comparison (general):
Dioxane–water: excellent for Suzuki couplings; good base solubility; elevated temperatures needed.
2-MeTHF/CPME: greener alternatives to THF/DCM; often compatible with cross-coupling and carbonyl chemistry; check solubility case-by-case.
Storage and Reconstitution
Item-specific storage and shipping:
Storage conditions: Room temperature (as provided in Product Data). Protect from light to preserve the aryl iodide functionality. Keep container tightly closed in a dry, well-ventilated place.
Shipped in: Normal.
General handling and stability notes:
Aryl iodides are typically air-stable solids or oils but can be light sensitive. Store in amber glass or protect the container with foil if long-term storage on the bench is expected.
Moisture sensitivity: not strongly hygroscopic in general, but keep dry to maintain assay and avoid hydrolysis of any sensitive impurities.
Reconstitution: Not applicable. Dissolve directly in a suitable organic solvent (e.g., DCM, EtOAc, THF, MeCN, DMF, or DMSO) immediately before use. Solubility is substrate- and solvent-dependent; verify on small scale. If particulate persists, gentle warming and sonication can assist dissolution.
Freeze–thaw: not relevant unless preparing stock solutions. For solution stocks (e.g., in dry DMSO or MeCN), store aliquots under inert gas at −20 to 4 °C, protected from light, and avoid repeated freeze–thaw cycles.
Shelf life: Not specified for this item; refer to CoA/Spec Sheet. Periodically check by TLC/HPLC or NMR for signs of decomposition (e.g., iodine formation, dehalogenated byproducts).
Structure and Identity
Item-specific identifiers provided: CAS 898784-06-0; InChIKey: 55794 (as provided); 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.
Structural features (general, based on the name):
The name 2-(4-Chlorophenyl)-2'-iodoacetophenone indicates an aryl ketone (acetophenone core) bearing two halogenated aryl substituents: one ring containing a para-chloro substituent and the other bearing an iodo substituent at the position denoted with a prime (′), i.e., on the ring associated with the acetophenone nucleus.
Functional groups: a conjugated aryl ketone (–CO–Ar) and at least one aryl iodide (Ar–I) plus an aryl chloride (Ar–Cl). These confer distinct reactivity handles for cross-coupling and carbonyl chemistry.
2D description (general): a benzene ring carrying an acetyl (–CO–CH3) or benzoyl-like linkage to a second halogenated aryl ring; one phenyl ring has a para-chloro substituent, while the other phenyl ring contains an iodine substituent at an ortho or ring position designated 2′ relative to the carbonyl connection.
Notes on identity:
Exact atom connectivity, stereochemistry (if any), and canonical descriptors (SMILES/InChI) are Not specified for this item; refer to CoA/Spec Sheet. The compound is expected to be a single-component, non-chiral aryl ketone unless otherwise stated.
For unambiguous structure confirmation and registry matching, consult the product’s CoA and SDS, which will list definitive identifiers and spectral data references where available.
Synthetic Utility
As a bifunctional aryl ketone featuring an aryl iodide and a para-chloroaryl substituent, this reagent offers orthogonal reactivity that enables stepwise diversification:
Chemoselective cross-coupling: Exploit the high reactivity of Ar–I to install complex fragments under Pd catalysis (Suzuki, Sonogashira, Heck). Subsequently, address the Ar–Cl under more forcing Pd/Ni conditions (e.g., BrettPhos/Buchwald systems, or Ni(dppe) catalysis), enabling two distinct C–C/C–N/C–O bond constructions from a single scaffold.
Carbonyl elaboration: Convert the ketone to oximes/hydrazones (then reduce to amines via Wolff–Kishner or hydrogenation), perform Baeyer–Villiger to generate aryl esters/phenols, or reduce to secondary alcohols for further activation (e.g., Mitsunobu inversions are not applicable here but derivatization is possible).
Halogen–lithium exchange: Rapid exchange at the iodide with s‑BuLi at low temperature (e.g., −78 °C) affords an aryllithium that can be trapped with CO2, electrophiles (DMF → aldehyde, B(OMe)3 → boronate), or used in directed ortho-metalation sequences depending on substituent patterns.
Photoredox/radical: Aryl iodides are privileged substrates for generation of aryl radicals, enabling Minisci-type C–H functionalization or Giese additions in the presence of suitable catalysts and donors.
Late-stage functionalization: The scaffold accommodates installation of heteroaryl motifs, alkenes, alkynes, or amines to build libraries for materials or ligand development.
This orthogonality streamlines retrosynthesis and parallel synthesis strategies.
Target Specificity
Not applicable. This product is a small-molecule organic reagent, not a biological targeting reagent (e.g., antibody, ligand standard with defined receptor specificity). No antigen, epitope, species reactivity, clone, or isotype information applies.
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