2-(4-Chlorophenyl)-1-(2-fluorophenyl)ethanone - ≥95% , CAS No.1183199-32-7

CAS: 1183199-32-7 Cat. No.: C1052772 Summenformel: C₁₄H₁₀ClFO Molekulargewicht: 248.68 PubChem CID: 22399523

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Spezifikationen & Reinheit

≥95%

Storage

Room temperature

Reinheit

≥95%

Namen und Kennungen

Kanonisches Lächeln

C1=CC=C(C(=C1)C(=O)CC2=CC=C(C=C2)Cl)F

IUPAC Name

2-(4-chlorophenyl)-1-(2-fluorophenyl)ethanone

InChIKey

BHHYZUFRAHGUGC-UHFFFAOYSA-N

INCHI

1S/C14H10ClFO/c15-11-7-5-10(6-8-11)9-14(17)12-3-1-2-4-13(12)16/h1-8H,9H2

Isomere SMILES

C1=CC=C(C(=C1)C(=O)CC2=CC=C(C=C2)Cl)F

PubChem CID

22399523

Molekulargewicht

248.68

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 Fluorobenzenes Chlorobenzenes Aryl fluorides Aryl chlorides Vinylogous halides Organofluorides Organochlorides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Stilbene - Alkyl-phenylketone - Phenylketone - Aryl alkyl ketone - Aryl ketone - Benzoyl - Chlorobenzene - Fluorobenzene - Halobenzene - Aryl chloride - Aryl fluoride - Aryl halide - Monocyclic benzene moiety - Benzenoid - Vinylogous halide - Ketone - Organohalogen compound - Organochloride - Organofluoride - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - 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: 248.680 g/mol
• XLogP3: 3.900
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 248.04 Da
• Monoisotopic Mass: 248.04 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

Application Protocols

No manufacturer-validated biological assay protocols are provided for this SKU. As a synthetic intermediate, usage protocols are reaction-specific.

• General laboratory workflow suggestions
  • For cross-couplings: establish a catalyst/ligand screen (e.g., Pd/XPhos family) across 2–3 solvents and 2 bases; monitor by LC–MS.
  • For enolate chemistry: calibrate base strength and temperature using a small-scale titration; confirm enolate formation by in situ IR or 1H NMR (α-CH2 disappearance).
  • Purification: start with silica gel column using hexanes/EtOAc gradients; check for tailing due to polarity and adjust with 1–2% Et3N in eluent if needed.

Refer to the Reaction Conditions and Synthetic Utility tabs for more detailed guidance.

Biological Roles

This molecule is a synthetic aryl ketone building block and is not a known endogenous metabolite or biochemical cofactor.

• General considerations (literature)

  • Aryl ketones can engage in photochemical processes under UV, potentially generating reactive species; avoid unnecessary UV exposure during handling.
  • Fluoro- and chloro-substituted biaryls are common motifs in bioactive libraries; however, any biological activity of this exact compound would be context-dependent and is not established here.

• Research context

  • Potential use as an intermediate when exploring structure–activity relationships (SAR) in medicinal chemistry campaigns, where substituent effects (ortho-F, para-Cl) modulate electronics and lipophilicity of downstream targets.

No medical or clinical claims are made. Use is limited to research and laboratory applications.

Buffer Applications

Not typically applicable. This compound is a hydrophobic organic building block rather than a buffering agent or aqueous additive.

• Practical note
  • If used in biochemical assays, dissolve first in a suitable water-miscible organic co-solvent (e.g., DMSO, acetonitrile, or ethanol) and then dilute into buffer, ensuring final co-solvent content is compatible with the assay.

For buffer recipes and pH control, select established buffer systems (e.g., phosphate, HEPES) independent of this compound.

Green Alternatives

While the compound itself is a non-solvent building block, greener choices can be made in its handling and transformations.

• Greener solvent options (literature guidance)

  • Replace chlorinated solvents (DCM/CHCl3) with ethyl acetate, methyl tert-butyl ether (MTBE), or 2-methyltetrahydrofuran (2-MeTHF) where solubility permits.
  • For cross-couplings, consider water/ethanol mixtures or CPME/2-MeTHF as reaction media with modern catalyst systems.

• Energy and process considerations

  • Microwave or flow-assisted coupling can reduce reaction times and energy input compared to prolonged reflux in high-boiling polar aprotics.
  • Crystallization-driven purifications can minimize silica usage; explore antisolvent pairs like EtOAc/hexanes or MeOH/water (if feasible).

• Comparative snapshot (general)

  • DMF vs 2-MeTHF: DMF offers broad solubility and high-temperature stability but has EHS and regulatory burdens; 2-MeTHF is bio-derived with better safety, though sometimes lower solubilizing power.
  • DCM vs EtOAc: DCM excels at rapid extractions; EtOAc is less toxic and biodegradable, with slightly slower phase separation and potentially higher solvent volumes.

• Halogen management

  • The substrate contains Cl and F; minimize halogenated waste by optimizing coupling selectivity and employing catalytic rather than stoichiometric halogen-based reagents.

These recommendations are general and should be validated against your specific transformation and purity targets.

Pharmaceutical Uses

No pharmacopeial or excipient status is indicated for this item, and no formulation role is specified in the Product Data.

• General context (literature)

  • Fluoro/chloro biaryl ethanones may serve as intermediates in the synthesis of candidate APIs or advanced intermediates due to their tunable electronics and cross-coupling handle (para-Cl).
  • The ketone function allows diversification via reductive, oxidative, and condensative transformations to reach pharmacologically relevant scaffolds.

• Development considerations

  • For GMP or clinical manufacturing, dedicated qualification, impurity profiling, and change control are required; this product is provided for research use only.

No therapeutic claims are made for this compound.

Physical Properties

Item-specific specifications for this SKU (e.g., melting point, boiling point, density, solubility, UV cutoff) are not provided in the Product Data.

• Item-specific specs

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Purity/grade: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed properties (non-binding guidance; verify experimentally)

  • Molecular formula: C14H10ClFO (structure-derived)
  • Formula weight: ~248.68 g/mol (calculated)
  • Physical state: typically a crystalline solid or low-melting solid for diaryl ethanones of this substitution pattern (literature trend).
  • Solubility profile (typical): sparingly soluble in water; soluble in common organic solvents such as dichloromethane, chloroform, toluene, THF, acetone, and ethyl acetate (literature/general for hydrophobic aryl ketones).
  • Lipophilicity: expected logP in the moderate-to-high range due to two aryl rings and halogens (qualitative literature expectation).

• Practical notes (general)

  • The benzylic methylene adjacent to the carbonyl can slowly discolor upon prolonged light exposure; store protected from light for best stability (general for aryl benzyl ketones).
  • For precise property values relevant to your lot (e.g., mp, residual solvents), consult the Aladdin CoA/Specification Sheet for C1052772.

Quality and Grades

The Product Data do not specify a grade or purity for this item. For exact release criteria (assay, identification, and impurity limits), please refer to the Aladdin CoA/Specification Sheet for SKU C1052772.

• Item-specific status

  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.

• Context on common grades (general guidance)

  • Research-grade: Suitable for most synthetic chemistry workflows; purity typically ≥95% by HPLC/GC unless otherwise noted.
  • High-purity/analytical grade: Tighter control of non-volatile residue and UV-absorbing impurities; used when spectroscopic baselines or sensitive kinetics matter.
  • Screening/HTS grade: Emphasis on structural identity for library synthesis, with pragmatic purity thresholds.

• Stabilizers/impurities

  • No stabilizers are indicated in the Product Data. Aryl ketones seldom require stabilizers; however, trace residual solvents or inorganic salts from synthesis may be present within specification limits (general).

• What to check on receipt (best practice)

  • Verify identity by 1H/13C NMR and HRMS against the expected structure.
  • Assess purity by HPLC or GC where applicable; check water content by Karl Fischer if moisture-sensitive reactions are anticipated.
  • Record appearance and any discoloration for your batch file.

Reaction and Applications

As a 2,4-halogenated diaryl ethanone, this building block combines an activated benzylic position with a cross-coupling handle.

• Key reactivity motifs (general/literature)

  • Benzylic methylene activation: The α-CH2 adjacent to the carbonyl is readily deprotonated to form enolates for alkylation, acylation, or condensation (e.g., Claisen–Schmidt to styryl ketones/chalcones; Knoevenagel-type variants with suitable partners).
  • Electrophilic aromatic substitution is deactivated by F/Cl; nucleophilic aromatic substitution (SNAr) is generally not favored for a simple ortho-F without extra ring activation.
  • Cross-coupling at para-Cl: Suzuki–Miyaura, Buchwald–Hartwig, Negishi, or Sonogashira couplings under Pd catalysis using aryl chloride-capable ligands (e.g., dppf, XPhos, SPhos) enable diversification.
  • Alpha-functionalization: α-halogenation (NBS/NCS), α-azidation, or α-hydroxylation (via enolate/oxaziridine) to access densely functionalized intermediates.

• Typical applications (examples)

  • Synthesis of fluorinated/chlorinated biaryl frameworks with controlled electronics for materials or medicinal chemistry.
  • Assembly of heterocycles via condensation with nitrogen nucleophiles (e.g., imidazoles, quinazolines) after suitable α-activation.
  • Precursor to diketones/benzils by benzylic oxidation, enabling access to ligands and photophysical scaffolds.

• Practical tips

  • For enolate chemistry, rigorously dry, oxygen-free conditions improve yields and selectivity; quench at low temperature to minimize over-alkylation.
  • For Pd-catalyzed couplings on aryl chloride, employ robust ligand systems and elevated temperatures (80–120 C) with strong bases (K3PO4, Cs2CO3) and adequate degassing.
  • Monitor potential dehalogenation side reactions and adjust catalyst/ligand loading accordingly.

Reaction Conditions

Representative conditions below are literature-style guidelines for aryl chlorides and benzylic ketones; optimize for your substrate and scale.

• Suzuki–Miyaura coupling at para-Cl (general)

  • Catalyst: Pd(dppf)Cl2·DCM (1–3 mol%) or Pd-PEPPSI/XPhos systems.
  • Base: K3PO4 or Cs2CO3 (2–3 equiv).
  • Solvent: 1,4-dioxane/H2O, toluene/H2O, or DMF.
  • Temperature/time: 80–110 C, 2–16 h under N2; degas thoroughly.

• Buchwald–Hartwig amination (general)

  • Catalyst/ligand: Pd2(dba)3 (1–2 mol%) with XPhos/SPhos/BrettPhos (2–5 mol%).
  • Base: NaOtBu or Cs2CO3.
  • Solvent: Toluene, dioxane, or t-BuOH.
  • Temperature: 90–120 C; monitor for dehalogenation.

• Enolate alkylation at the benzylic position (general)

  • Base: LDA or LiHMDS (1.1–1.5 equiv) in dry THF or ether at −78 to 0 C.
  • Electrophiles: primary alkyl halides, Michael acceptors, or acyl donors (Weinreb amides for controlled acylation).
  • Quench: cold NH4Cl or AcOH; warm slowly to minimize side reactions.

• Reductions/oxidations (general)

  • NaBH4 or catalytic hydrogenation (Raney Ni/Pd-C) for carbonyl to alcohol at 0–25 C in MeOH/EtOH.
  • MnO2 or SeO2 for benzylic/allylic oxidations in DCM/toluene at rt–80 C.

Yields and times depend on substrate and scale; consult primary literature for closely related examples.

Safety and Handling

No item-specific GHS classification, H-statements, or pictograms are provided in the Product Data for this SKU. Always consult the product SDS for authoritative safety information.

• General hazard considerations (literature/analogous compounds)

  • Aryl ketones and halogenated aromatics can cause skin/eye irritation and may be harmful if swallowed or inhaled. Avoid dust formation and aerosolization.
  • Not expected to be volatile; main exposure routes are dermal and ingestion.

• Recommended PPE and engineering controls (good laboratory practice)

  • Wear lab coat, safety glasses or chemical splash goggles, and appropriate chemically resistant gloves (e.g., nitrile). Handle in a fume hood during weighing, transfers, and reactions.
  • Avoid strong oxidizers and strong bases until compatibility is assessed; benzylic positions can undergo halogenation/oxidation under harsh conditions.

• Storage and incompatibilities

  • Storage: Room temperature (per Product Data); keep container tightly closed in a dry, well-ventilated area; protect from light to minimize discoloration (general).
  • Incompatibilities (general): strong oxidizers, strong bases or nucleophiles in the presence of reactive halides; moisture has minimal impact but keep desiccated for analytical consistency.

• First-aid overview (general)

  • Skin/eye contact: Rinse with water for several minutes; remove contaminated clothing; seek medical attention if irritation persists.
  • Inhalation: Move to fresh air; obtain medical advice if symptoms occur.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.

Refer to the SDS for full GHS classification, first-aid, firefighting measures, and spill response.

Solvent Selection

This compound is a nonpolar-to-moderately polar aromatic ketone. Solvent choice is typically driven by target reaction class and desired solubility.

• General solubility/miscibility profile (literature/typical)

  • Good: dichloromethane (DCM), chloroform, toluene, THF, dioxane, acetone, acetonitrile, ethyl acetate.
  • Limited: alcohols (MeOH/EtOH) may dissolve upon warming; water is expected to be very poor.

• Selection guidance by application (general)

  • Enolate chemistry/alpha-functionalization: anhydrous THF, MTBE, or toluene with LDA, LiHMDS, or NaH; temperature control from −78 to 0 C.
  • Cross-coupling on the para-chloro ring: polar aprotic solvents (DMF, DMAc, NMP) or toluene/1,4-dioxane mixtures; water or t-BuOH as co-solvent for base solubility.
  • Crystallization/purification: hot EtOH/MeOH or EtOAc/hexanes mixtures are typical starts for screen development.

• Comparisons (general)

  • DCM vs. EtOAc: DCM offers higher solubility and faster workups; EtOAc is a greener alternative with slightly lower solvent power.
  • DMF/NMP vs. 2-MeTHF/dioxane: DMF/NMP enhance coupling rates at high temperature but have EHS burdens; 2-MeTHF/dioxane balance performance with improved safety.

Note: The above are literature-based guidelines. Confirm solubility and compatibility with your specific lot and reaction conditions.

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.
  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.

• General handling

  • Keep tightly closed in a dry, well-ventilated place. Protect from light to mitigate potential discoloration common to benzylic aryl ketones.
  • If long-term storage is anticipated, consider desiccation and amber glass containment.

• Reconstitution/dissolution (general)

  • For stock solutions, dissolve in dry organic solvents such as DMSO, acetonitrile, THF, or dichloromethane based on intended use. Filter if necessary (PTFE membrane) to remove particulates.
  • Record solvent, concentration, and date. For DMSO or ACN stocks intended for assay use, aliquot and store at −20 C to minimize freeze–thaw cycles.

Always consult the CoA and SDS for lot-specific guidance and stability information.

Structure and Identity

A diaryl ethanone bearing ortho-fluoro and para-chloro substituents; an electrophilic aryl ketone with a benzylic methylene linking two rings.

• Item-specific (Product Data)

  • Product name: 2-(4-Chlorophenyl)-1-(2-fluorophenyl)ethanone
  • CAS: 1183199-32-7
  • PubChem CID: 22399523
  • InChIKey: 24897 (as provided)
  • Storage: Room temperature
  • Research Use: For research use only

• Computed/Literature identity (for reference; not item specifications)

  • Molecular formula (structure-derived): C14H10ClFO
  • Exact mass/Formula weight (calculated): ~248.68 g/mol
  • Representative SMILES (literature): Fc1ccccc1C(=O)CH2c2ccc(Cl)cc2
  • Core features: One aryl ketone (–CO–) flanked by a 2-fluorophenyl (ortho-F) and a 4-chlorophenyl (para-Cl) ring; benzylic CH2 adjacent to carbonyl (activated methylene); no stereogenic centers.

• 2D structural description (general)

  • The molecule comprises two aromatic rings connected by an acetyl linkage. The carbonyl is bonded to the 2-fluorophenyl ring, and the alpha-methylene (–CH2–) connects to the 4-chlorophenyl ring. Electron-withdrawing F and Cl modulate ring electronics, affecting reactivity under cross-coupling and enolate chemistry.

Synthetic Utility

This substrate integrates three strategic elements—an aryl chloride (coupling handle), an ortho-fluoro aryl ring (electronic tuning), and a benzylic methylene adjacent to a ketone (α-chemistry)—making it highly adaptable in multistep synthesis.

• Transformations (literature/general)

  • Cross-coupling at para-Cl: Suzuki (boronic acids/esters), Buchwald–Hartwig (amines), Sonogashira (alkynes), Negishi (organozincs). Ortho-F typically remains intact, enabling subsequent diversification.
  • Enolate-based elaboration: LDA/LiHMDS-mediated alkylation or acylation at the benzylic position; Claisen–Schmidt condensations to E-styryl ketones; formation of β-diketones and 1,3-dicarbonyl derivatives.
  • Functional group interconversions: Reduction to secondary alcohol (NaBH4, catalytic hydrogenation), Wolff–Kishner or Clemmensen to the diarylethane, Baeyer–Villiger oxidation to aryl esters/phenols after rearrangement.
  • Benzylic oxidation: SeO2, MnO2, or TEMPO-based protocols to access α,β-dicarbonyls or benzils for ligand/materials applications.

• Strategic value

  • Orthogonal reactivity: perform Pd-catalyzed diversification first, then engage α-chemistry; or vice versa depending on base sensitivity of the installed group.
  • Electronics: ortho-F subtly raises aryl C–H acidity and affects conformational preferences; para-Cl provides a balance between reactivity and stability under storage and handling.

This versatility supports rapid library expansion and convergent route design.

Target Specificity

Not applicable. This product is a small-molecule chemical building block, not a biological macromolecule or affinity reagent. No antigen/epitope, clone, isotype, or species reactivity information applies.

Häufig gestellte Fragen

What is the purity of this product?

This product is supplied at ≥95% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 1183199-32-7, the molecular formula is C14H10ClFO, and the molecular weight is 248.68 g/mol. InChIKey BHHYZUFRAHGUGC-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.