Ethanone, 2-(3-chlorophenyl)-1-(4-chlorophenyl)- - ≥97% , CAS No.68968-12-7

CAS: 68968-12-7 Cat. No.: E1031667 PubChem CID: 58573710

GRADE & PURITY ≥97%

Storage

Room temperature

Specifications

Spezifikationen & Reinheit

≥97%

Storage

Room temperature

Reinheit

≥97%

Namen und Kennungen

• Kanonisches Lächeln: C1=CC(=CC(=C1)Cl)CC(=O)C2=CC=C(C=C2)Cl
• IUPAC Name: 2-(3-chlorophenyl)-1-(4-chlorophenyl)ethanone
• InChIKey: VRURULNDNOWMGE-UHFFFAOYSA-N
• INCHI: 1S/C14H10Cl2O/c15-12-6-4-11(5-7-12)14(17)9-10-2-1-3-13(16)8-10/h1-8H,9H2
• Isomere SMILES: C1=CC(=CC(=C1)Cl)CC(=O)C2=CC=C(C=C2)Cl
• PubChem CID: 58573710

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Klasse Stilbenes

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Klasse: Stilbenes
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Stilbenes
• Alternative Parents: Alkyl-phenylketones Benzoyl derivatives Aryl alkyl ketones Chlorobenzenes Aryl chlorides Organochlorides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Stilbene - Alkyl-phenylketone - Phenylketone - Aryl alkyl ketone - Aryl ketone - Benzoyl - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - Monocyclic benzene moiety - Benzenoid - Ketone - Organic oxygen compound - Organohalogen compound - Organochloride - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Aromatic homomonocyclic compound
• Beschreibung: 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

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

Chemische und physikalische Eigenschaften

• Molekulargewicht: 265.100 g/mol
• XLogP3: 4.400
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 264.011 Da
• Monoisotopic Mass: 264.011 Da
• Topological Polar Surface Area: 17.100 Ų
• Heavy Atom Count: 17
• Formal Charge: 0
• Complexity: 259.000
• 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

Application Protocols

No vendor-validated bioassay or analytical protocols are provided for this item. Typical laboratory uses include synthetic transformations (reductions, enolate chemistry, cross-couplings). For chromatography or reaction monitoring, standard TLC (UV 254 nm) and LC–MS methods for aryl ketones are appropriate.

Research Use Note: For research use only.

Biological Roles

This product is a synthetic aromatic ketone building block and is not a known endogenous biomolecule.

• No established metabolic or signaling role is documented for this specific structure in biological systems (literature generalization for diaryl ketones).
• In research, diaryl ketones often serve as scaffolds for SAR exploration in medicinal chemistry; however, this product is supplied strictly for laboratory research and synthetic use.

Research Use Note: For research use only. Not intended for human or veterinary diagnostic, therapeutic, or clinical applications.

Buffer Applications

Not typically applicable. This compound is a hydrophobic aromatic ketone and does not function as an aqueous buffer component. For practical handling in biology-oriented workflows, prepare stock solutions in suitable organic co-solvents (e.g., DMSO or ethanol) and dilute into assay media if required by a specific protocol.

Green Alternatives

Greener practices for handling and transforming diaryl ketones focus on solvent selection, safer oxidants/reductants, and catalyst systems that activate aryl chlorides efficiently at lower loadings.

• Preferred solvents: Replace chlorinated solvents with ethyl acetate, 2-MeTHF, CPME, or propylene carbonate when compatible. For reductions, ethanol or isopropanol are preferable to methanol/THF blends.
• Catalysis: Employ ligand-enabled Pd or Ni catalysts that activate aryl chlorides under mild conditions (aqueous base, ethanol/water, or 2-MeTHF) to minimize energy input and waste.
• Oxidants/Reductants: Choose H2 with heterogeneous catalysts for reductions instead of stoichiometric hydrides where feasible; for Baeyer–Villiger, consider H2O2/enzymatic systems in place of peracids.

Comparison (general):

• Process aspect | Conventional option | Greener alternative | Trade-offs
• — | — | — | —
• Solvent for workup | DCM | Ethyl acetate | Slightly higher solvent volumes; safer profile
• Ether solvent | THF | 2-MeTHF/CPME | Different azeotropes; sometimes slower rates
• Reduction | NaBH4 in MeOH | H2 with Pd/C in EtOH | Requires hydrogen handling and pressure control
• Oxidation | mCPBA in DCM | H2O2 or biocatalysis | Substrate scope/chemoselectivity may differ

Note: Validate substitutions on small scale; aryl chloride cross-couplings can be sensitive to solvent and ligand choice.

Pharmaceutical Uses

No excipient or compendial role is specified for this item. As a diaryl ketone, it may be used in medicinal chemistry as a synthetic intermediate to explore aryl–alkyl ketone chemotypes and to access substituted benzhydrols, aryl esters (via Baeyer–Villiger), or elaborated biaryl motifs after cross-coupling at aryl chlorides.

• Regulatory status (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Typical formulation role (general): Building block only; not a standard pharmaceutical excipient.

Research Use Note: For research use only. Not intended for drug, household, or other uses.

Physical Properties

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point / Boiling point: Not specified for this item; refer to CoA/Spec Sheet.
• Density / Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (item-specific): Not specified for this item; refer to CoA/Spec Sheet.

General/literature-based physicochemical expectations for diarylethanones (for context only):

• Phase/volatility (literature): Typically low-volatility solids or high-boiling oils due to dual aryl substitution and conjugation.
• Solubility profile (literature): Sparingly soluble in water; soluble in common organic solvents such as dichloromethane, chloroform, toluene, THF, ethyl acetate, acetone; high solubility in polar aprotics (DMF, DMSO).
• Polarity/logP (literature): Moderate lipophilicity from two aryl rings; polar carbonyl enables H-bond accepting interactions; logP generally elevated relative to acetophenones.
• Spectroscopy (literature): Strong IR carbonyl band near ~1670–1690 cm−1 for aryl–alkyl ketones; 1H NMR shows benzylic methine ~4.5–5.5 ppm (desoxybenzoin-type), aromatic multiplets 7.0–8.0 ppm; 13C NMR carbonyl ~195–200 ppm.

Note: Values above are general literature characteristics for related diaryl ketones and are provided for guidance only. For exact specifications of SKU E1031667, consult the product CoA/Spec Sheet.

Quality and Grades

• Grade/Purity (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers/Inhibitors (item-specific): Not specified for this item; refer to CoA/Spec Sheet.

General guidance for interpreting grades (context for diaryl ketone building blocks):

• Research grade: Suitable for synthetic chemistry, method development, and discovery. Typical impurity profile includes trace isomers, residual solvents, or halogenated by-products; actual limits are defined in the CoA.
• Analytical/Chromatography grade (if applicable): Tight control of UV baseline-absorbing impurities for photometric or chromatographic work.
• Impurity considerations for aryl ketones (general):
  • Potential regioisomeric diaryl ketones or unreacted aryl precursors.
  • Trace halides or oxidative by-products (e.g., benzylic alcohols or dicarbonyls) depending on the synthesis route.
  • Water content generally low; hygroscopicity is minimal compared with polar inorganic salts.

What to check on the CoA for this item:

• Assay/purity method (GC, HPLC, or qNMR), limit of related substances, residual solvent profile, and identity confirmation (1H/13C NMR, IR, MS).
• If chiral evaluation is relevant, whether the material is racemic or enantioenriched (for this structure it is commonly racemic unless specified).

Reaction and Applications

As a 1,2-diarylethanone, this compound is a versatile intermediate in synthesis and SAR exploration for aryl–alkyl ketone scaffolds.

• Reductions to secondary alcohols: Sodium borohydride, DIBAL-H, or catalytic hydrogenation (Raney Ni/Pd-C) afford the benzylic carbinol (1-(4-chlorophenyl)-2-(3-chlorophenyl)ethanol). Control temperature and equivalents to avoid over-reduction to the hydrocarbon.
• Baeyer–Villiger oxidation: Peracids or mCPBA can convert the aryl–alkyl ketone to an aryl acetate/benzoate derivative; migration preferences favor the more substituted/aryl group.
• Alpha-functionalization:
  • Enolate alkylation/acylation: Using LDA/NaHMDS to introduce substituents at the benzylic α-position.
  • Halogenation: NBS/NCS for benzylic bromination/chlorination via enol/radical pathways; subsequent substitution expands diversity.
• Cross-coupling downstream: The aryl chlorides tolerate Pd-catalyzed cross-couplings (Suzuki–Miyaura, Buchwald–Hartwig amination, Sonogashira) with appropriate ligands capable of activating aryl chlorides (e.g., BrettPhos/XPhos systems), enabling late-stage diversification.
• Condensations: Claisen–Schmidt condensation from the ketone to stilbene analogs under basic or acidic conditions; Knoevenagel-type with activated methylenes.
• Photochemical reactivity (general for aryl ketones): Triplet-excited states can engage in H-abstraction and EDA processes; ensure deoxygenation to limit quenching.

Practical tips:

• Ensure anhydrous conditions for strong-base enolate chemistry; dry solvents and inert atmosphere improve selectivity.
• Monitor by TLC (UV-active, strong absorption) and by LC–MS; aryl chloride mass fragments are diagnostic (Cl isotopic pattern).

Reaction Conditions

General literature guidance for transforming diaryl ethanones; optimize for your system.

• Enolate alkylation:
  • Base: LDA or NaHMDS (1.1–1.5 equiv) in THF/2-MeTHF.
  • Temperature: −78 to −20 °C for deprotonation; warm to 0–25 °C for electrophile addition.
  • Electrophiles: Allyl/benzyl halides, alkyl triflates; typical reaction times 0.5–3 h after addition.
• Reduction to alcohol:
  • NaBH4 (1–2 equiv) in MeOH, EtOH, or i-PrOH/THF at 0–25 °C, 0.5–2 h; quench with NH4Cl.
  • Catalytic hydrogenation: 5–10 wt% Pd/C, 1–3 bar H2 in EtOH/EtOAc, 20–40 °C, 2–6 h. Monitor for dehalogenation; adjust catalyst/solvent accordingly.
• Baeyer–Villiger oxidation:
  • mCPBA (1.2–1.5 equiv) in DCM at 0–25 °C, 2–12 h; or H2O2 with catalytic acid in fluorinated/alcoholic media (longer times, greener profile).
• Benzylic halogenation:
  • NBS/AIBN in CCl4, PhH, or greener alternatives like PhMe/MeCN under photolysis/thermal (60–90 °C), 1–6 h; affords α-bromoketone for further elaboration.
• Cross-coupling at aryl chloride:
  • Suzuki–Miyaura: Pd2(dba)3 (1–2 mol%), XPhos/BrettPhos-type ligands (2–4 mol%), base K3PO4 or Cs2CO3, solvent 2-MeTHF/toluene/H2O, 60–100 °C, 4–16 h.
  • Buchwald–Hartwig amination: Pd catalysts with dialkylbiaryl phosphines; 80–110 °C in toluene/1,4-dioxane.

Notes:

• The carbonyl and benzylic C–H can coordinate/react; consider protecting strategies or orthogonal sequences when coupling and α-functionalization are both planned.
• Always monitor for competitive dehalogenation under hydrogenation conditions.

Safety and Handling

• GHS classification, signal word, H-statements, pictograms (item-specific): Not specified for this item; refer to SDS.
• General hazards (literature/analog-based): Aromatic ketones may cause skin/eye irritation and are harmful if swallowed. Avoid inhalation of dust/aerosols. Aryl chlorides can be persistent; prevent release to the environment.
• PPE: Lab coat, safety glasses or goggles, nitrile gloves. Use in a chemical fume hood to control vapors/particulates during weighing and transfers.
• Handling notes:
  • Avoid prolonged exposure to heat and direct sunlight.
  • Prevent contact with strong bases/strong oxidizers; base-catalyzed enolization can occur.
  • For reactions generating fine particulates, minimize dust and implement local exhaust.
• First aid (summary; defer to SDS):
  • Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present and easy; seek medical attention if irritation persists.
  • Skin: Wash with soap and water; remove contaminated clothing.
  • Inhalation: Move to fresh air; seek medical attention if symptoms occur.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
• Spill/cleanup: Absorb small spills with inert material (vermiculite), collect for disposal. Avoid environmental discharge.
• Fire safety: Use CO2, dry chemical, or foam. Combustion may produce HCl/HCl-containing fumes and CO/CO2. Store away from ignition sources.

Always consult the product-specific SDS for authoritative safety information.

Solvent Selection

This compound is a moderately polar, hydrophobic diaryl ketone. Solvent choice is driven by solubility, reaction mechanism (enolization, reductions, couplings), and workup efficiency.

• Polarity class (general): Nonpolar to moderately polar organic solute; strong H-bond acceptor (C=O), no H-bond donor.
• Miscibility/Solubility (literature):
  • Good: DCM, chloroform, toluene, ethyl acetate, acetone, acetonitrile, THF, 2-MeTHF, MTBE (warm), DMF, DMSO.
  • Poor: Water; alkanes may require heating or co-solvent.
• Chromatography: Normal-phase silica using hexanes/ethyl acetate gradients typically resolves diaryl ketones; reverse-phase C18 with MeCN/H2O (0.1% acid) is also effective when necessary.
• Reaction-driven choices:
  • Enolate chemistry (alkylation/aldol): THF, 2-MeTHF, or DME under strong base (LDA, NaHMDS) at −78 to 0 °C.
  • Reductions (NaBH4, catalytic hydrogenation): Protic/aprotic mixtures (EtOH/THF, MeOH/THF) for NaBH4; EtOH, EtOAc, or AcOH for catalytic hydrogenation.
  • Photochemistry/EDA processes: Acetonitrile or DCM preferred for transparency.
• Workup: Liquid–liquid extraction from DCM/EtOAc into aqueous phases is straightforward; brine wash to break emulsions; charcoal treatment removes colored by-products.

Comparison note:

• Versus highly polar ketones, this substrate requires less polar eluents; versus trihalomethyl ketones, it is more benign and easier to handle. Choose greener ethers/esters (2-MeTHF, EtOAc) where feasible.

Storage and Reconstitution

• Storage conditions (item-specific): Room temperature (as provided in Product Data). Store tightly capped in a dry place, away from direct light and sources of ignition.
• Shipping: Not specified for this item; refer to CoA/Spec Sheet.
• Stability: Aryl ketones are generally stable under ambient conditions. Avoid prolonged exposure to strong light and bases to limit undesired enolization or side reactions.
• Reconstitution/stock preparation (general):
  • Prepare concentrated stocks in dry organic solvents compatible with the intended use: DMSO, DMF, acetonitrile, THF, toluene, or ethyl acetate.
  • For bioassay contexts, DMSO or ethanol stocks (e.g., 10–100 mM) are typical; filter through 0.22 μm if particulate is present.
• Freeze–thaw: Not generally required; if solutions are prepared, store aliquots to avoid repeated freeze–thaw cycles, particularly in DMSO where moisture uptake can occur.
• Container compatibility: Glass vials with PTFE-lined caps are recommended, especially for long-term storage and to prevent permeation.

Always consult the item’s CoA and SDS for definitive storage and handling instructions.

Structure and Identity

A di(aryl)ethyl ketone bearing two chloro-substituted phenyl rings; a versatile aromatic building block for synthesis.

• Product name: Ethanone, 2-(3-chlorophenyl)-1-(4-chlorophenyl)- (desoxybenzoin analog)
• CAS: 68968-12-7 (item-specific)
• PubChem CID: 58573710 (item-specific)
• 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.

Structural features (general description of this structure):

• Core motif: 1,2-diarylethanone (Ar–CO–CH(Ar′)) with a ketone carbonyl flanked by two aromatic rings.
• Ring substitution: One ring is 4-chlorophenyl (para-chloro) attached to the carbonyl carbon; the other is 3-chlorophenyl (meta-chloro) attached to the α-carbon.
• Functional groups: A conjugated aryl ketone (propiophenone/desoxybenzoin family), two aryl chlorides (C–Cl on benzene).
• Stereochemistry: The benzylic center (α to carbonyl) is sp2–sp3; however, no stereocenter is present because it bears H, COAr, and Ar′ (three different substituents yield chirality only if four are different; here one substituent is hydrogen, so it is chiral only if the two aryls are different, which they are—thus, in principle, the α-carbon is a stereocenter. Commercial material is typically racemic unless specified; item-specific configuration is not specified).
• 2D verbal depiction: A carbonyl (C=O) bonded to a para-chlorophenyl on the acyl side; the α-carbon (adjacent methine) bears a hydrogen and is bonded to a meta-chlorophenyl ring.

Synthetic Utility

Key features that make this compound valuable in synthesis:

• Dual aryl handles (aryl chlorides): Each ring can be selectively functionalized under Pd/Ni catalysis. Para-chloro and meta-chloro positions have distinct reactivity profiles; with modern bulky biaryl phosphines (e.g., BrettPhos, XPhos), aryl chlorides engage efficiently in Suzuki, Buchwald–Hartwig, and Sonogashira couplings.
• Benzylic α-position: The methine adjacent to the carbonyl is activated for enolate formation, enabling:
  • α-Alkylation/acylation to build contiguous stereocenters.
  • Aldol/Claisen-type condensations to extend carbon frameworks.
  • Halogenation (NBS/NCS) followed by SN1/SN2 or cross-coupling after conversion to benzylic pseudohalides.
• Carbonyl transformations:
  • Reduction to secondary alcohols (stereocontrol possible with chiral catalysts/auxiliaries).
  • Oxidation to dicarbonyls or rearrangement (Baeyer–Villiger) to aryl esters.
  • Deoxygenation (Wolff–Kishner, Clemmensen) for hydrocarbon frameworks.
• Photochemistry and EDA: Aryl ketones can participate in triplet-mediated hydrogen abstraction or serve as acceptors in donor–acceptor complexes, enabling C–C coupling strategies.

These features position the molecule as a flexible node in retrosynthetic planning to access substituted benzylic alcohols, stilbenes, triarylmethanes, and polyaryl architectures.

Target Specificity

Not applicable. This product is a small-molecule aromatic ketone and is not an antibody, enzyme, or biologic. No target-binding specificity is provided for this item.