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
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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
300.300 g/mol
XLogP3
3.800
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
7
Exact Mass
300.116 Da
Monoisotopic Mass
300.116 Da
Topological Polar Surface Area
43.400 Ų
Heavy Atom Count
22
Formal Charge
0
Complexity
383.000
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
Calcolatori di soluzioni
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Recensioni
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Application Protocols
No application protocols are provided for this item in the Product Data. As a general-purpose research chemical, protocols will be specific to the synthetic transformation or analytical method selected by the user.
General suggestions (non-specific):
Analytical characterization: Acquire 1H/13C NMR, 19F NMR (for the fluorophenyl), IR (carbonyl bands), LC-MS/HRMS, and HPLC purity. Calibrate chemical shifts with internal standards; verify integration vs assay.
Purification: Start with normal-phase silica gel using hexanes/EtOAc gradients; adjust with DCM if necessary. Consider recrystallization from EtOAc/hexane or toluene/hexane if the material solidifies.
Sample preparation for screening: Prepare stock solutions in anhydrous DMSO (e.g., 10–50 mM), filter through 0.22 µm PTFE, and store aliquots at −20 °C to limit freeze–thaw.
For any specific synthetic or analytical protocol, validate conditions on small scale prior to scale-up and consult primary literature for analogous substrates.
Biological Roles
This product is offered strictly for research and laboratory use. No biological role or function is assigned to this specific catalog item in the provided data.
General considerations (not specific to this item):
Aromatic ketone/ester scaffolds are common synthetic intermediates used to access libraries of small molecules for biochemical screening. The embedded carbonyls can be diversified to furnish alcohols, amides, heterocycles, or conjugated systems evaluated in medicinal chemistry campaigns.
The presence of a meta-fluorophenyl group is often leveraged in medicinal chemistry to modulate lipophilicity, metabolic stability (blocking oxidative sites), and binding conformations; however, no claims are made here regarding biological activity of this exact compound.
Compliance: Do not use in humans or animals. No pharmacological, toxicological, or clinical claims are made or implied. For any biological testing, ensure appropriate institutional approvals and SDS-informed risk assessments are in place.
Buffer Applications
Not typically applicable. 3'-Carboethoxy-3-(3-fluorophenyl)propiophenone is a hydrophobic organic building block, not a buffering agent. It lacks acid/base pairs suitable for preparing aqueous buffers in physiological pH ranges.
Practical note:
If handling this compound in bioassay workflows, dissolution is usually performed in DMSO or other water-miscible organic co-solvents, followed by dilution into assay media. Solubility limits and potential precipitation should be empirically evaluated; no item-specific solubility data are provided.
For chromatography or analytical sample prep, mobile-phase modifiers (e.g., formic acid, ammonium acetate) may be used to optimize peak shape, but these are properties of the mobile phase rather than this compound.
Green Alternatives
Green chemistry considerations here focus on solvent and reagent choices used with this aromatic ketone/ester building block. No item-specific green certifications are provided.
Greener solvent substitutions (general guidance):
Replace dichloromethane/chloroform with 2-MeTHF, CPME, EtOAc, or toluene where polarity permits. These alternatives lower halogenated waste and often enable easier solvent recovery.
For enolate chemistry, 2-MeTHF can substitute for THF with similar coordinating ability and a higher boiling point; drying is still essential.
For extractions, EtOAc or MTBE can supplant DCM; for crystallizations, consider EtOAc/hexanes instead of DCM/hexanes.
Catalysis and reagent choices:
Favor catalytic hydrogenation or transfer hydrogenation for carbonyl reductions when compatible, reducing metal hydride waste.
Apply micellar catalysis for cross-couplings (TPGS-750-M in water) to reduce organic solvent volumes, acknowledging solubility constraints for hydrophobic substrates.
Comparison snapshot (general):
DCM vs EtOAc: EtOAc has lower toxicity profile, is bio-derived compatible; may require adjusted elution strength.
THF vs 2-MeTHF: 2-MeTHF is from renewable feedstocks and forms peroxides more slowly; similar performance in many base-mediated steps.
DMF/DMAc vs MeCN/propylene carbonate: Where feasible, shift to lower-toxicity polar aprotics; validate reaction rates and selectivity.
Note: Validate green substitutions on small scale; ester/ketone chemoselectivity can shift with solvent polarity and water content.
Pharmaceutical Uses
No pharmacopeial status or excipient role is provided for this item. It is supplied for research use only and is not intended for drug, household, or other uses.
General context (not specific to this item):
Aromatic ketone/ester intermediates are common in medicinal chemistry routes as advanced building blocks or masked functionalities (e.g., ester as a handle for later amidation or hydrolysis). Such intermediates may appear in non-GMP discovery routes but are ordinarily resynthesized or upgraded to GMP-grade for development.
The meta-fluoro substituent is frequently employed to adjust metabolic clearance and binding properties in candidate molecules; however, that pertains to downstream derivatives rather than this catalog item.
Regulatory note: If considering use in a regulated environment, request detailed CoA, impurity profile, and any available route-of-synthesis information. Qualification and re-testing under your internal quality system are required.
Physical Properties
Item-specific specifications (from Product Data):
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.
General/literature expectations for compounds of this class (aryl ketone bearing an ethyl ester and a 3‑fluorophenyl substituent; informational only, not specifications for this item):
Physical state: Typically a pale solid or viscous oil depending on purity and crystallinity; aromatic ketone–ester hybrids can show moderate melting ranges.
Boiling/Melting: Many diaryl ketone/ester derivatives melt between ~50–120 °C and decompose or distill at reduced pressure; exact values are structure dependent (literature, analogous compounds).
Density: Often in the 1.15–1.30 g/mL range for fluorinated aryl ketones/esters (literature, analogous compounds).
Solubility: Poorly soluble in water; good solubility expected in moderately polar organic solvents (DCM, CHCl3, EtOAc, THF, acetone) and in aromatic hydrocarbons (toluene). Limited solubility in alkanes (general behavior).
Partitioning: LogP expected >2, typical for triaryl/aryl‑ester systems (literature, analogous compounds).
Refractive index: If liquid, nD typically ~1.53–1.60 for aryl carbonyl compounds (literature, analogous compounds).
Note: For authoritative item-specific physical constants and analytical acceptance criteria (UV cutoff, residual solvents, water content, metal limits), consult the current CoA/Specification Sheet. Do not use literature estimates as purchasing or QC specifications.
Quality and Grades
Item-specific details:
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on grades for synthetic building blocks (general):
Research grade: Suitable for discovery chemistry and method development; typically accompanied by NMR/LC-MS purity reporting on CoA. If your application is impurity-sensitive (e.g., medicinal chemistry SAR or materials fabrication), request detailed impurity profiling and chromatographic purity reports.
HPLC/GC suitability: If used as an analytical reference or in trace-level synthesis, choose a grade with low non-volatile residue and documented UV background. Low-UV or HPLC grade refers to solvent quality; for solids, seek high assay with residual solvent and water content reporting.
Stabilizers: Not indicated for this item. If present in related products, stabilizers are listed explicitly on the label/CoA and may affect downstream reactions (e.g., need for removal by chromatography or washing).
Verification and documentation:
Identity confirmation: CoA typically provides 1H NMR and LC-MS. For carbonyl/ester compounds, IR (C=O stretches ~1735 cm⁻¹ for ester, ~1680 cm⁻¹ for aryl ketone) is a useful orthogonal check (general guidance).
If your synthesis is moisture- or base-sensitive, consider re-drying and re-checking assay by qNMR prior to scale-up.
For this specific catalog item, defer to the Aladdin CoA/Spec Sheet for the exact assay method, impurity limits, residual solvents, and any stabilizers.
Reaction and Applications
Context: 3'-Carboethoxy-3-(3-fluorophenyl)propiophenone is positioned as a multifunctional aryl carbonyl building block combining an aryl ketone (propiophenone motif) with an ethyl ester and a 3‑fluorophenyl substituent. This constellation enables diverse reactivity and late-stage diversification.
Typical application families (general literature guidance):
Enolate chemistry: The benzylic alpha position to the ketone can undergo deprotonation (e.g., LDA, NaHMDS) enabling alkylation, aldolizations, or intramolecular cyclizations. Competing reactivity at the ester under strong base should be considered (Claisen-type condensations).
Reductions: Chemoselective reduction strategies allow conversion of the ketone to secondary alcohols (NaBH4, CBS), or global reductions to diols/alcohol–ester combinations (DIBAL-H, LiAlH4 with caution re: ester).
Cross-coupling on aryl rings (after halogen exchange/introduction if needed): Suzuki–Miyaura, Buchwald–Hartwig, or Sonogashira couplings can be employed to elaborate the aromatic framework; the meta-fluoro substituent can be leveraged for SNAr on suitably activated systems.
Cyclizations: Intramolecular Friedel–Crafts or Michael-type closures from enolates can access benzofused or tetralone-like scaffolds; Dieckmann or Claisen strategies may be leveraged due to the embedded ester.
Heterocycle formation: The 1,3-dicarbonyl equivalent behavior (ketone + ester) supports Knoevenagel condensations and subsequent heteroannulations (e.g., pyranone/pyridone accesses depending on partners, literature precedent for analogous substrates).
Practical tips:
Control base strength and temperature to favor ketone enolization versus transesterification.
Protect from moisture during strong-base steps; dry glassware and anhydrous solvents.
Monitor by LC-MS/UPLC due to distinct chromophores (aryl + carbonyls), facilitating sensitive detection.
Reaction Conditions
General literature guidance for typical operations on aryl ketone/ethyl ester substrates (not item-specific specifications):
Enolate alkylation/aldolization: LDA or NaHMDS (1.1–1.5 equiv) in dry THF or 2‑MeTHF at −78 to −20 °C, 0.5–4 h. Quench with NH4Cl. Compete with Claisen pathways if ester enolizes; consider kinetic control and temperature rigor.
Selective ketone reduction: NaBH4 (1–2 equiv) in MeOH/THF at 0 to 25 °C, 0.5–2 h; CeCl3 (Luche) can improve 1,2‑selectivity in the presence of conjugation. Avoid ester reduction by maintaining mild conditions.
Ester to acid: Aqueous NaOH or K2CO3 in MeOH/THF/H2O (pH >12) at rt to 50 °C, 1–6 h; acidify to precipitate the acid. Alternatively, LiOH in THF/H2O for milder conditions.
Ester to amide: Carbodiimide (EDC·HCl)/HOBt or uronium reagents (HATU, TBTU) in DMF/MeCN with amine nucleophiles, 0 to 25 °C. For direct aminolysis, heat neat ester with amine or use catalytic DMAP in toluene (Dean–Stark if needed).
Global reductions: DIBAL‑H at −78 to −20 °C for partial reductions; LAH in THF/Et2O at 0 to reflux can reduce both carbonyls—use with caution.
Aromatic diversification: For SNAr on fluorinated rings, strong bases (NaOMe, t‑BuOK) in polar aprotics (DMF/DMSO) at 50–120 °C if additional ring activation is present; for Pd couplings, toluene/dioxane/EtOH–water systems with bases like K2CO3 or Cs2CO3, 60–110 °C.
Yields: Highly substrate- and condition-dependent; analogous literature reports span 50–90% for well-optimized steps. Always perform small-scale scouting and in-process controls.
Safety and Handling
Item-specific hazard information (from Product Data):
Signal Word: Not specified for this item; refer to SDS.
H-Statements: Not specified for this item; refer to SDS.
GHS Classification: Not specified for this item; refer to SDS.
Pictograms: Not specified for this item; refer to SDS.
General safety guidance for aromatic ketone/ester intermediates (informational only; defer to SDS for this item):
Likely hazards: May cause skin/eye irritation and respiratory irritation. Avoid inhalation of dusts/aerosols and contact with skin/eyes.
PPE: Wear safety glasses or goggles, lab coat, and appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood to control vapors/particulates.
Handling: Avoid strong bases and strong nucleophiles if ester stability is required; avoid strong oxidizers; protect from prolonged UV light which can promote photochemistry of carbonyls.
First aid summary: If on skin/eyes, rinse with plenty of water for at least 15 minutes; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth and seek medical attention. Always follow institutional SOPs.
Fire safety: Treat as a combustible organic. Use CO2, dry chemical, or foam. Carbonyl compounds may produce irritating fumes under fire conditions.
Spills: Absorb small spills with inert material (vermiculite, silica) and dispose of according to local regulations. Prevent release to drains.
Always consult the product’s SDS for authoritative hazard classification, exposure limits, and response procedures.
Solvent Selection
Applicability: As a non-ionic aromatic ketone/ester building block, solvent choice primarily impacts handling, purification, and reactivity in synthetic steps rather than “buffering.”
General solvent behavior (literature/general):
Polarity class: Moderately lipophilic; dissolves well in mid-polar organic solvents (DCM, CHCl3, EtOAc, THF, acetone, acetonitrile) and aromatic hydrocarbons (toluene). Poorly soluble in water.
Dielectric context: Reactions involving enolate formation or acylations often benefit from polar aprotic solvents (THF, DMF, DMSO, MeCN) to stabilize ionic intermediates. For crystallizations, toluene/hexane or EtOAc/hexane systems are common starting points.
Purification: Normal-phase silica gel chromatography with hexanes/EtOAc or hexanes/DCM gradients is typical. The presence of both ketone and ester functions can increase polarity versus simple hydrocarbons, aiding separation.
When to choose alternatives (general guidance):
Replace dichloromethane with EtOAc, toluene, or 2-MeTHF when feasible to improve sustainability.
For strong-base steps (e.g., LDA enolizations), rigorously dry ether solvents (THF, 2-MeTHF) and maintain low temperature.
For metal-catalyzed couplings on the aryl rings (if pursued), mixtures such as toluene/EtOH/water or dioxane/water with appropriate bases can be effective.
Note: No item-specific solubility specifications are provided; verify solubility empirically on your sample prior to process selection.
Storage and Reconstitution
Item-specific storage (from Product Data):
Storage Conditions: Room temperature.
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
General storage guidance for aromatic ketone/ester intermediates:
Keep container tightly closed in a dry, well-ventilated place. Protect from prolonged light exposure which can promote carbonyl photochemistry.
Desiccation: Beneficial to limit hydrolysis of the ester under humid conditions; store with a desiccant when feasible.
Inert atmosphere: Not strictly required for most aryl ketone/ester solids, but a nitrogen blanket is prudent for long-term storage.
Reconstitution/solution handling (if needed):
Solvents: DMSO, DMF, acetone, acetonitrile, dichloromethane, THF, or ethyl acetate generally provide good solubility (general guidance; verify experimentally).
Stock solutions: Prepare at known concentration, filter through 0.22 µm PTFE, and store in amber vials. For sensitive transformations, prepare fresh solutions to minimize adventitious hydrolysis or reduction.
Freeze–thaw: If solutions are stored refrigerated or frozen, aliquot to avoid repeated freeze–thaw cycles that may introduce moisture and degrade esters.
Always consult the current CoA and SDS for definitive storage and handling recommendations for this specific batch.
Structure and Identity
Brief overview: 3'-Carboethoxy-3-(3-fluorophenyl)propiophenone is an aromatic ketone/aryl–ester derivative intended as a synthetic building block for research use.
Computed/literature-identification notes (general, not specifications for this item):
Expected functional groups: an aryl ketone (propiophenone motif), a 3-fluorophenyl substituent, and an ethyl ester (carboethoxy) substituent on the aromatic system. These features suggest a conjugated diaryl ketone core bearing an ester on one ring.
Ring systems: Two benzene rings; one likely fluorinated at the meta position; one bearing an ethyl carboxylate substituent.
Stereochemistry: None expected at fully substituted carbonyl carbons; the molecule is achiral in the absence of restricted rotation or atropisomerism.
Not specified for this item; refer to CoA/Spec Sheet:
Molecular formula
Molecular weight
SMILES
2D structure described in words (general): an acyl–aryl framework akin to propiophenone, substituted at the benzylic/alpha position by a 3‑fluorophenyl group, with the other aryl ring bearing an ethyl ester (–CO2Et) substituent at the 3′-position.
Synthetic Utility
Strategic value (general, for aryl ketone + ethyl ester systems):
Bifunctionality: The coexistence of an aryl ketone (electrophilic carbonyl with enolizable alpha position) and an ethyl ester (amenable to saponification, amidation, or reduction) allows orthogonal synthetic maneuvers. Sequencing steps to exploit chemoselectivity is key.
Enolate control: Base choice can bias reactivity toward the ketone alpha position (LDA, −78 °C, THF) vs ester transformations (Claisen/Dieckmann). Temporary protection of one carbonyl (e.g., ketalization) can further refine selectivity.
Diversification handles: The 3‑fluorophenyl group can participate in SNAr when paired with additional ring activation or serve as a handle in late-stage C–H activation protocols.
Representative transformations (literature for analogous substrates):
Condensations: Knoevenagel with aldehydes to form α,β‑unsaturated systems; subsequent intramolecular cyclizations enable access to flavone/chalcone-like motifs.
Cross-coupling: After installation of halides or pseudohalides, Pd-catalyzed couplings diversify the aryl rings while retaining the carbonyl framework.
Process notes:
Monitor for transesterification in alcoholic solvents under acidic/basic conditions.
Fluorinated aromatics can alter retention factors; adjust chromatography eluents accordingly.
Employ orthogonal analytics (1H/13C NMR, 19F NMR, LC-MS) to track chemoselectivity and fluorine integrity.
Target Specificity
Not applicable. This product is a small-molecule chemical building block, not a biological reagent or antibody. No target, epitope, or isotype information is associated with this catalog item.
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