3',5'-Dichloro-3-(3-fluorophenyl)propiophenone , CAS No.898767-65-2

CAS: 898767-65-2 Cat. No.: D947527 Formula: C₁₅H₁₁Cl₂FO Peso molecolare: 297.15 PubChem CID: 24726158

Storage

Room temperature

Specifications

Condizioni di conservazione di stoccaggio

Room temperature

Nomi e identificatori

• Sorrisi canonici: C1=CC(=CC(=C1)F)CCC(=O)C2=CC(=CC(=C2)Cl)Cl
• IUPAC Name: 1-(3,5-dichlorophenyl)-3-(3-fluorophenyl)propan-1-one
• InChIKey: RQJBRGNWIDMMDO-UHFFFAOYSA-N
• INCHI: 1S/C15H11Cl2FO/c16-12-7-11(8-13(17)9-12)15(19)5-4-10-2-1-3-14(18)6-10/h1-3,6-9H,4-5H2
• Isomeri SMILES: C1=CC(=CC(=C1)F)CCC(=O)C2=CC(=CC(=C2)Cl)Cl
• PubChem CID: 24726158
• Peso molecolare: 297.15

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Classe Linear 1,3-diarylpropanoids
      • Subclass Chalcones and dihydrochalcones

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Classe: Linear 1,3-diarylpropanoids
• Subclass: Chalcones and dihydrochalcones
• Intermediate Tree Nodes: Not available
• Direct Parent: Retro-dihydrochalcones
• Alternative Parents: Alkyl-phenylketones Butyrophenones Dichlorobenzenes Benzoyl derivatives Aryl alkyl ketones Fluorobenzenes Aryl fluorides Aryl chlorides Organofluorides Organochlorides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Retro-dihydrochalcone - Alkyl-phenylketone - Butyrophenone - Phenylketone - Benzoyl - 1,3-dichlorobenzene - Aryl ketone - Aryl alkyl ketone - Chlorobenzene - Fluorobenzene - Halobenzene - Aryl halide - Aryl fluoride - Benzenoid - Monocyclic benzene moiety - Aryl chloride - Ketone - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Organooxygen compound - Organofluoride - Organohalogen compound - Organochloride - Aromatic homomonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as retro-dihydrochalcones. These are a form of normal dihydrochalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions.
• 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

Proprietà chimiche e fisiche

• Peso molecolare: 297.100 g/mol
• XLogP3: 4.900
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 296.017 Da
• Monoisotopic Mass: 296.017 Da
• Topological Polar Surface Area: 17.100 Ų
• Heavy Atom Count: 19
• 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: 1

Application Protocols

Not applicable. No biological assay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule building block. For synthetic procedures, see Reaction Conditions and Synthetic Utility sections for general guidance.

Biological Roles

This product is a synthetic, halogenated diaryl ketone intended for laboratory research and chemical synthesis. It is not a metabolite, cofactor, or biopolymer building block, and it does not have a known intrinsic biological role.

• General context (not item-specific claims)
  • Aryl ketones can interact with biological targets via hydrophobic and π–π interactions; halogenation typically increases lipophilicity and can modulate membrane association and metabolic stability. These are general structure–property observations rather than specific activities.
  • The carbonyl can undergo biotransformations (e.g., reduction to secondary alcohols) in metabolic systems, but no biological pathway assignment is available for this exact compound.

Research Use Note: For research use only. No medical, diagnostic, or clinical use is intended or implied.

Buffer Applications

Not typically applicable. This compound is a hydrophobic organic building block rather than a buffering agent. It does not form defined buffer systems in aqueous media. For practical handling, dissolve in a suitable organic solvent before use or formulation, and consult Solvent Selection and Synthetic Utility sections for guidance.

Green Alternatives

• Solvent choices

  • Prefer greener solvents where feasible: 2-MeTHF or CPME (as ether alternatives to THF/Et2O) and ethyl acetate or propylene carbonate in place of DCM for extractions/purifications when compatible with the chemistry.
  • For Pd-catalyzed cross-couplings on aryl chlorides, bio-derived 2-MeTHF or aqueous micellar catalysis (TPGS-750-M systems) can reduce VOC impact; note that aryl chlorides may need elevated temperature and carefully chosen ligands in water-rich media.

• Energy and process considerations

  • Aryl chloride activation often requires higher temperatures; consider continuous-flow heating (better heat transfer, reduced solvent inventory) to improve safety/efficiency.
  • Explore base/ligand systems enabling lower catalyst loadings to reduce precious metal usage.

• Comparison snapshot (general)

  • DCM/CHCl3: excellent solubility, but poor EHS profile → consider EtOAc or toluene where workable.
  • THF: versatile, but peroxide-forming and from fossil feedstocks → 2‑MeTHF (bio-sourced), CPME (lower peroxide tendency) as alternatives.
  • Strong hydrides (LiAlH4): effective but hazardous → catalytic hydrogenation (Raney Ni, Pd/C) in greener solvents when substrate-compatible.

Trade-offs: Halogenated substrates may necessitate non-aqueous, higher-boiling media and strong bases; greener replacements should be validated for yield/selectivity on this specific substrate.

Pharmaceutical Uses

No pharmacopeial monograph or excipient role is indicated for this item. As a halogenated aryl ketone, it may serve as a synthetic intermediate in the preparation of drug candidates or discovery compounds; however, this product is supplied strictly for research and laboratory synthesis.

• Formulation context (general)
  • If used in screening libraries or preclinical chemical biology, stocks are typically prepared in high-purity DMSO or acetonitrile and stored in inert vials to minimize adsorption and hydrolysis (arylated ketones are generally stable).
  • Avoid claims of therapeutic function; any downstream use in regulated contexts requires independent qualification and GMP sourcing.

Item-specific regulatory status, residual solvent profile, and elemental impurities: Not specified for this item; refer to CoA/Spec Sheet.

Physical Properties

Item-specific physical constants are not provided for this catalog entry.

• Item-specific values

  • Appearance: 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.

• Literature/expected behavior for halogenated diaryl ketones (context only; not specifications)

  • Phase at ambient conditions: typically low-melting solids or high-boiling oils depending on substitution; halogenation often raises melting point and boiling point relative to unsubstituted analogs.
  • Solubility: generally sparingly soluble in water; readily soluble in common organic solvents (e.g., dichloromethane, chloroform, ethyl acetate, THF, acetone) and in aromatic hydrocarbons. Fluorine and chlorine substituents increase lipophilicity.
  • Polarity/logP: aryl ketones are moderately polar; halogenation increases logP (exact value not available for this structure).
  • UV: aryl ketones exhibit π→π* absorption in the UV; halogenation perturbs λmax and ε (quantitative data not available here).

For authoritative, lot-specific data (mp, bp, density, purity, UV cutoff, residuals), please consult the CoA/Spec Sheet for this SKU.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

• Guidance on grades (general context)

  • Research grade: suitable for most synthetic applications; impurity profiles vary by lot and supplier. If chromatographic or photophysical studies are planned, request UV/trace impurity data.
  • High-purity or HPLC grade (when available): features tighter limits on residual solvents, low non-volatile residue, and controlled UV absorbance—beneficial for analytical or photochemical work.
  • Stabilizers: none indicated for this item. If supplied stabilized in some cases, verify impact on planned reactions (e.g., hindered bases, amines, or trace acids can affect enolate chemistry). For this listing, stabilizers are Not specified for this item; refer to CoA/Spec Sheet.

• What to check on the CoA/Spec Sheet

  • Assay/purity method (GC, HPLC, NMR integration), residual solvent profile, water content, halide/metal traces if relevant to catalysis, and chromatographic identity.
  • Item-specific specifications (mp/bp, UV cutoff, elemental analysis) are Not specified for this item; refer to CoA/Spec Sheet.

If you require tighter impurity controls for cross-coupling or asymmetric catalysis, contact us for custom QC or pre-screened lots.

Reaction and Applications

As a 3,5-dichloro/3-fluoro diaryl propiophenone, this molecule is a versatile intermediate in halogenated aryl ketone chemistry.

• Transformations of the carbonyl

  • Reductions: aryl ketone → secondary alcohol (NaBH4 with activation; NaBH(OAc)3 not typical; LiAlH4 or catalytic hydrogenation more forceful). Wolff–Kishner or Clemmensen for full deoxygenation (conditions sensitive to substituents).
  • Oxime/hydrazone formation (NH2OH, hydrazines) enabling subsequent Beckmann or Wolff rearrangements (substrate-dependent).
  • Enolate chemistry: α-alkylation/acylation under LDA/NaHMDS; formation of chalcone-like systems via aldol with aromatic aldehydes from the methylene adjacent to the carbonyl.

• Aryl–X functionalization handles

  • Two aryl chlorides (meta, meta′ on the benzoyl ring) are potential sites for Pd-catalyzed cross-coupling (Buchwald–Hartwig amination, Suzuki–Miyaura, Negishi), though aryl chlorides generally require stronger ligation (e.g., BrettPhos/XPhos) and higher temperatures.
  • The 3-fluoro substituent is robust under many conditions; SNAr is unlikely without additional activation but can direct ortho-lithiation for further elaboration.

• Strategic applications

  • Building block for densely substituted biaryl-propyl motifs.
  • Useful for SAR exploration in agrochemical/materials discovery where halogen patterning modulates lipophilicity and electronic properties.

Manufacturer applications: Not specified in product data; this section reflects general synthetic uses of aryl propiophenones.

Reaction Conditions

General literature guidance for transformations relevant to halogenated diaryl propiophenones (illustrative; optimize per substrate):

• Ketone → alcohol (reduction)

  • NaBH4: MeOH, 0–25 °C, 2–12 h; aryl ketones may be sluggish—add CeCl3·7H2O (Luche conditions) or switch to NaBH4 in IPA with catalytic NiCl2. Yields vary widely (40–90%).
  • Catalytic hydrogenation: Pd/C (5–10 wt%), EtOH or EtOAc, 1–5 bar H2, 20–50 °C, 2–8 h; can reduce carbonyl and potentially dehalogenate—monitor selectivity.

• Enolate alkylation

  • LDA (1.1–1.5 equiv) in THF, −78→0 °C, add alkyl halide (1.2–2.0 equiv); 1–4 h. Quench with NH4Cl. Typical isolated yields 50–85% depending on electrophile.

• Oxime formation

  • NH2OH·HCl (1.5–2.0 equiv), pyridine or Et3N in EtOH/MeOH, 25–60 °C, 2–16 h; isolate oxime, then optional Beckmann rearrangement (H2SO4, SOCl2, or POCl3 systems).

• Cross-coupling on aryl chloride positions

  • Suzuki–Miyaura: Pd2(dba)3 (1–2 mol%) + XPhos/BrettPhos (2–4 mol%), K3PO4 or Cs2CO3, toluene/dioxane or 2‑MeTHF/H2O (4:1), 80–110 °C, 6–18 h.
  • Buchwald–Hartwig amination: Pd(OAc)2 (1–3 mol%), BrettPhos or RuPhos (2–6 mol%), NaOtBu, toluene or CPME, 90–120 °C, 8–20 h.

• Ortho-lithiation (fluoro-directed)

  • s-BuLi (1.1–1.5 equiv) in THF at −78 °C, 0.5–2 h, then electrophile (CO2, DMF, I2). Strict anhydrous conditions.

These are literature-style ranges, not item-specific specifications. Always verify halogen tolerance to avoid undesired dehalogenation.

Safety and Handling

• GHS and hazard statements (item-specific)

  • Signal word: Not specified for this item; refer to SDS.
  • H-statements: Not specified for this item; refer to SDS.
  • GHS classification/pictograms: Not specified for this item; refer to SDS.

• General safety guidance for aryl ketones (informational; defer to SDS)

  • Likely hazards: may cause skin/eye irritation and respiratory irritation; avoid inhalation of dust/aerosols and contact with skin/eyes.
  • PPE: lab coat, safety glasses or splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a chemical fume hood to control vapors/dust.
  • Incompatibilities: strong oxidizers (risk of exotherm); strong bases may form enolates; reactive metals. Avoid strong reducing agents unless intended for reaction (e.g., hydride reductions).
  • First aid (overview): in case of skin contact, wash with soap and water; eye contact, rinse cautiously with water for several minutes and seek medical advice; inhalation, move to fresh air; ingestion, rinse mouth—seek medical attention. Always follow institutional protocols.
  • Spill/cleanup: contain and collect with inert absorbent for disposal; prevent entry into drains. Ventilate area and use appropriate PPE.

Consult the Aladdin SDS for SKU D947527 for definitive hazard classification, exposure limits, and response measures.

Solvent Selection

This compound is a halogenated diaryl ketone with moderate polarity and high aromatic character.

• Miscibility/solubility (literature expectations)

  • Good solubility: chlorinated solvents (DCM, CHCl3), ethers (THF, 2-MeTHF, MTBE), esters (EtOAc), ketones (acetone, MEK), and aromatics (toluene).
  • Limited solubility: alcohols (MeOH/EtOH) variably soluble; water—very low solubility.

• Polarity class and dielectric context

  • Moderately polar aprotic solute; benefits from solvents that solvate aromatics and carbonyls. For enolate chemistry, polar aprotic ethers (THF, DME) are typical; for electrophilic aromatic reactions, nonpolar aromatics can moderate rates/selectivity.

• Selection tips by use case

  • Purification: normal-phase silica with hexane/EtOAc or hexane/DCM gradients often effective; halogenation increases Rf vs. hydrocarbon analogs. Reverse-phase (C18) with ACN/H2O + 0.1% acid for analytical HPLC.
  • Reductions (NaBH4 less reactive on aryl ketones): use MeOH/THF or EtOH with additives; for stronger hydrides (LiAlH4), use dry ether solvents.
  • Cross-coupling on aryl chlorides: toluene, dioxane, or CPME with polar co-solvent (t-BuOH, DMAc) under Pd/Buchwald ligand systems.

Item-specific solubility parameters are Not specified for this item; refer to CoA/Spec Sheet.

Storage and Reconstitution

• Storage (item-specific)

  • Storage conditions: Room temperature (as provided in Product Data). Store tightly closed in a dry, well-ventilated place away from incompatible reagents (strong oxidizers, strong bases/acids when not in use). Protect from prolonged light and moisture.
  • Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

• Handling and stock solutions (general guidance)

  • Solid/oil handling: minimize atmospheric moisture uptake; recap promptly. If hygroscopicity is a concern, handle in a dry box or under inert gas.
  • Solution preparation: dissolve in dry organic solvent (e.g., DMSO, acetonitrile, THF, DCM, or EtOAc) to prepare concentrated stocks. Filter if particulates are present. Record solvent lots for reproducibility.
  • Storage of solutions: for mid-term storage, keep sealed under inert gas at 2–8 °C protected from light. Check stability by LC/MS or HPLC prior to critical use.

• Stability notes

  • Aryl ketones are generally stable under neutral, dry conditions. Avoid prolonged exposure to strong base (enolization) or strong acid (possible Friedel–Crafts side reactions). No stabilizer is indicated for this item.

For definitive shelf-life and retest dates, consult the lot-specific CoA.

Structure and Identity

3',5'-Dichloro-3-(3-fluorophenyl)propiophenone is a halogenated diaryl ketone (a β,β-diaryl aliphatic ketone) featuring a 3,5-dichloro-substituted benzoyl ring linked via a three‑carbon propiophenone backbone to a 3‑fluorophenyl group. The carbonyl is benzylic to one ring and β to the second ring, enabling typical aryl ketone reactivity.

• Item-specific identifiers (from Product Data)

  • CAS: 898767-65-2
  • CID: 24726158
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Computed/literature identifiers (for reference; not specifications)

  • Molecular formula (computed from name): C15H11Cl2FO
  • Molecular weight (computed): ~297.15 g/mol

• Structural features (general description)

  • Functional groups: aromatic rings (one 3,5-dichloro-substituted, one 3‑fluoro-substituted), aryl ketone (propiophenone core)
  • Connectivity: 3,5-dichlorophenyl–CO–CH2–CH2–(3‑fluorophenyl)
  • Stereochemistry: achiral as drawn (no stereogenic centers)
  • Electron-withdrawing substituents (Cl, F) on the rings decrease ring activation toward electrophilic substitution and influence cross-coupling behavior (aryl chlorides typically less reactive than bromides/iodides).

Synthetic Utility

Key functional elements make this scaffold a flexible node in multistep synthesis:

• Carbonyl-centered chemistry

  • Enolate generation (LDA/NaHMDS, −78 to 0 °C) from the methylene adjacent to the carbonyl enables C–C bond formation (alkylation, acylation, aldol). Diaryl substitution can stabilize the enolate and influence regioselectivity.
  • Chemoselective reductions convert the ketone to a secondary alcohol; further derivatization (esters, carbonates, carbamates) expands polarity and handles.
  • Imine-equivalents (oximes, hydrazones) serve as platforms for rearrangements or as protecting/activating groups.

• Aryl chloride vectors (meta, meta′ on benzoyl ring)

  • Pd-catalyzed couplings (Suzuki–Miyaura with aryl/alkyl boron species; Buchwald–Hartwig with amines; Kumada/Negishi for C–C) broaden diversity. Modern ligands (BrettPhos, XPhos, SPhos) enhance aryl chloride reactivity.

• Fluoroaryl ring tactics

  • The 3‑fluoro group can direct ortho-lithiation (−78 °C, s-BuLi) for subsequent electrophile quench, enabling late-stage substitution proximal to F.

• Retrosynthetic value

  • Accessible via Friedel–Crafts acylation to install the benzoyl fragment followed by cross-coupling or via acylation of a preformed biaryl ethane. The modular nature of the two aryl rings facilitates parallel synthesis for SAR or materials tuning.

Target Specificity

Not applicable. This product is a small-molecule chemical building block and is not an antibody, enzyme, or biological reagent with defined target specificity. No antigen/epitope or species reactivity information applies.