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
282.300 g/mol
XLogP3
3.700
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
7
Exact Mass
282.126 Da
Monoisotopic Mass
282.126 Da
Topological Polar Surface Area
43.400 Ų
Heavy Atom Count
21
Formal Charge
0
Complexity
344.000
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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Recensioni
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Application Protocols
Not applicable. No biology assay protocols (e.g., WB, IHC, IF, FC) or tested application dilutions are associated with this small-molecule building block in the Product Data.
General laboratory guidance:
For chemical synthesis, typical operations include dissolution in suitable organic solvent, inert-atmosphere handling for air/moisture‑sensitive steps, and purification by crystallization or column chromatography.
For biochemical assay screening, prepare concentrated stocks in DMSO or ethanol, filter (PTFE, 0.2 µm) if needed, and dilute into assay media while monitoring for precipitation.
Biological Roles
This product is an organic synthetic intermediate. No biological function, metabolism, or pathway role is provided in the Product Data.
Biological roles: Not typically assigned. Aryl–alkyl ketones with ester substituents are generally used as intermediates in discovery chemistry and materials synthesis rather than as biomolecules.
Biochemical reactivity (general): neutral, lipophilic molecules of this class may partition into lipid phases; they lack ionizable groups near physiological pH unless derivatized (e.g., saponification of the ester to a carboxylate).
In vitro handling: if used in biochemical assays, solvent carriers (e.g., DMSO) are commonly required due to low aqueous solubility. Keep final DMSO percentages low to avoid assay interference.
No medical or clinical claims are made. For research use only (per Product Data).
Buffer Applications
Not typically applicable. 3'-Carboethoxy-3-phenylpropiophenone is a neutral organic building block and does not function as a buffering agent.
If used in biochemical experiments, prepare stock solutions in compatible organic co-solvents (e.g., DMSO, ethanol) and dilute into the desired aqueous buffer while monitoring for precipitation. Optimize solvent percentages to maintain solubility without perturbing the biological system.
Green Alternatives
While 3'-Carboethoxy-3-phenylpropiophenone itself is a target/building block rather than a solvent, greener choices can be made in its synthesis, processing, and purification.
Solvent substitution (general recommendations):
Replace DCM/CHCl3 with EtOAc, MeTHF/2‑MeTHF, CPME, or toluene where feasible.
For enolate chemistry traditionally done in THF, evaluate 2‑MeTHF or CPME, which offer improved safety and renewable sourcing while retaining organometallic compatibility.
For polar aprotic needs (DMF, DMAc, NMP), consider safer alternatives like DMSO or propylene carbonate where compatible, or use dimethyl isosorbide as a high‑boiling green co‑solvent.
Oxidants/reductants:
Prefer catalytic hydrogenation over stoichiometric metal hydrides when chemoselectivity permits.
Use oxygen or H2O2 with appropriate catalysts for oxidations instead of peracids or Cr(VI), where substrate tolerance allows.
Workups/purification:
Minimize silica usage via crystallization or switch to recyclable chromatography media. Use heptane/EtOAc rather than hexane/EtOAc to reduce VOC toxicity profile.
Energy and atom economy:
Employ flow chemistry for hazardous steps (e.g., halogenation) to reduce solvent and improve heat/mass transfer.
Trade-offs: greener solvents may alter rates/selectivity (e.g., enolate geometry, aggregation). Validate on small scale and document changes in impurity profiles before scale-up.
Pharmaceutical Uses
No pharmacopeial or excipient status is provided in the Product Data, and this listing is not intended for therapeutic or clinical applications.
Potential role (general R&D context): serves as a synthetic intermediate in medicinal chemistry programs where the 1,3-diarylpropanone motif or its derived heterocycles are explored. The 3′‑carboethoxy group provides a handle for further derivatization (hydrolysis to acids, amide coupling, ester interchange).
Regulatory note: For research use only (per Product Data). Not for human or veterinary use, drug formulation, or diagnostic procedures.
Physical Properties
Item-specific specifications are not provided in the Product Data.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Purity/Grade: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Formula and Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Boiling point, melting point, density, refractive index, UV cutoff, water/peroxide/metal content: Not specified for this item; refer to CoA/Spec Sheet.
General characteristics (literature/structure-based expectations; not product specifications):
Physical state: many 1,3-diarylpropanones are low-melting solids or high-boiling oils; crystallinity depends on substitution pattern (the carboethoxy group can promote crystallinity via intermolecular interactions).
Solubility: expected to be sparingly soluble in water and freely soluble in common organic solvents (e.g., dichloromethane, chloroform, ethyl acetate, toluene, THF, acetonitrile, alcohols). Ester-bearing aryl ketones show good solubility in moderately polar aprotic media.
Acid/base behavior: neutral compound; enol/enolate formation possible at the methylene alpha to the carbonyl under basic conditions (typical pKa for benzylic alpha-CH of aryl ketones is in the high teens to low 20s; literature, approximate).
Partitioning: expected lipophilic character due to two aryl rings; the ester increases polarity modestly (literature expectation: high logP, qualitative).
Always consult the item’s CoA/Spec Sheet and SDS for authoritative physical specifications before process design.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpreting grades (general, for context only):
Research grade/technical grade: suitable for exploratory synthesis and screening; may contain higher levels of residual solvents or trace inorganic contaminants than analytical grades.
HPLC grade solvents/reagents: controlled for low UV absorbance and particulate content to minimize chromatographic background.
Stabilizers/inhibitors: not indicated in the Product Data. If present for analogous aromatic ketones or esters, stabilizers are typically unnecessary; verify on CoA if any additives are used.
Batch-specific documentation:
For this item, assay/purity, residual solvent profile, limit tests (water, metals), and spectroscopic identity tests (NMR/IR/HRMS) are Not specified for this item; refer to CoA/Spec Sheet.
If your application is sensitive to trace acids/bases (e.g., enolate chemistry, catalysis), request the latest CoA and, if needed, a tighter QC specification (e.g., peroxide content for stored solutions, Karl Fischer water, or low-halide).
Reaction and Applications
This molecule is a versatile intermediate within the 1,3-diarylpropanone class featuring an electron-withdrawing carboethoxy group on one ring. Typical research applications (general organic synthesis context):
Building block in medicinal and materials chemistry: the 1,3-diphenylpropanone scaffold serves as a platform for accessing heterocycles and extended conjugated systems. The 3′-carboethoxy substituent modulates electronics and can be further transformed (e.g., hydrolysis to acid, amidation, reductions).
Enolate chemistry at the alpha-methylene: under base (e.g., LDA, NaHMDS), the ketone forms enolates enabling C–C bond formation (alkylation, aldol, Michael additions). The benzylic stabilization often affords clean mono- vs di-alkylation with temperature control.
Cyclizations and annulations: intramolecular aldol or Friedel–Crafts-type condensations can furnish benzofuranone, indanone, or flavanone-like frameworks depending on substitution and conditions (Lewis acids such as AlCl3, BF3·OEt2, or Brønsted acids like H2SO4/PTS).
Carbonyl transformations:
Reductions (NaBH4, catalytic hydrogenation) to secondary alcohols; selective chemoselectivity tuning vs the ester via reagent choice.
Baeyer–Villiger oxidation (mCPBA) to aryl acetates/esters.
Wittig/Horner–Wadsworth–Emmons olefination to generate enones or stilbene-like extensions.
Aromatic functionalization: the 3′-carboethoxy ring is deactivated and meta-directing; electrophilic aromatic substitution proceeds sluggishly, while cross-coupling requires prior installation of leaving groups (e.g., halogenation via NBS/NCS or directed lithiation–quench sequences).
These use-cases should be adapted based on pilot experiments and the item’s actual purity and physical behavior (consult CoA).
Reaction Conditions
Representative conditions from general literature precedent for aryl–alkyl ketones and ester-bearing arenes (guidance only; not product-specific):
Enolate formation and alkylation:
Base: LDA (1.1–1.5 equiv) in THF or 2‑MeTHF at −78 to −20 °C; quench with primary alkyl halides to favor SN2.
Alternative: NaHMDS in THF/toluene; phase-transfer catalysis (K2CO3 or Cs2CO3, TBAB) in toluene/DMF for milder benzylations.
Aldol/Michael chemistry:
Aldol: TiCl4/Et3N or LDA then aldehyde addition at −78 to 0 °C; dehydration with p‑TsOH or POCl3/DMF (Vilsmeier) to form enones.
Michael additions onto activated alkenes in THF/DMF with secondary amines as catalysts (enamine) or using NaOMe/MeOH for base-promoted variants.
Carbonyl reductions:
NaBH4 or NaBH(OAc)3 in MeOH/THF at 0–25 °C for chemoselective ketone reduction; monitor to avoid unintended ester reduction.
Catalytic hydrogenation (Pd/C, 1–5 wt%) in EtOAc/EtOH under 1–5 bar H2 at ambient temperature selectively reduces the ketone in many systems.
Baeyer–Villiger oxidation:
mCPBA (1.2–1.5 equiv) in DCM at 0–25 °C; buffer with NaHCO3 to suppress acid-promoted side reactions.
Aromatic functionalization (on ester-bearing ring):
Electrophilic halogenation often requires directing or harsher conditions; directed ortho‑lithiation (sBuLi, −78 °C) adjacent to the ester, followed by electrophile quench, is a common strategy; ensure strict anhydrous conditions.
Yields and selectivities are substrate- and scale-dependent; run small-scale screenings, and consult the CoA/SDS for compatibility and safety before scale-up.
Safety and Handling
Authoritative safety classification is not provided in the Product Data.
GHS Classification, signal word, hazard statements, pictograms: Not specified for this item; refer to SDS.
General hazards (general chemistry guidance for aryl ketones/esters; not product-specific):
May cause irritation to skin, eyes, and respiratory tract. Avoid inhalation of dust/vapors and contact with skin/eyes.
Combustible organic compound; keep away from ignition sources. Use appropriate grounding/bonding when transferring organic liquids.
Personal protective equipment (PPE): lab coat, safety glasses or goggles, and suitable chemical-resistant gloves (e.g., nitrile). Use in a chemical fume hood.
Handling practices:
Prevent exposure by using closed systems or local exhaust.
Avoid strong bases/acids and strong oxidizers unless required by the procedure; aryl ketones undergo base-catalyzed enolization and can be oxidized under forcing conditions.
Storage incompatibilities: segregate from strong oxidizers and strong bases. Store in tightly closed container.
First aid (overview; consult SDS for details):
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: rinse with plenty of water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation develops.
Ingestion: rinse mouth; do not induce vomiting unless directed by medical personnel; seek medical attention.
Always defer to the product’s SDS for definitive safety, toxicological, and regulatory information.
Solvent Selection
This product is an organic building block (aryl–alkyl ketone with an ester-substituted aryl ring), not a solvent. However, solvent choice is critical for its handling, purification, and reactions.
Likely solubility profile (general guidance):
Good solubility in moderately polar aprotic solvents (DCM, CHCl3, EtOAc, THF, MeCN) and aromatic hydrocarbons (toluene). Limited solubility in water.
Polarity considerations:
The aryl ketone motif and ester-substituted ring increase dipolar interactions; aprotic polar solvents often enhance reaction rates for enolate chemistry and cross-couplings.
Selection by task (general):
Enolate generation/alkylation: THF, DME, or toluene with HMPA-free polar co-solvents; maintain anhydrous conditions.
Friedel–Crafts acylation workups and extractions: DCM/EtOAc–heptane systems aid phase separation and crystallization.
Cross-coupling on the ester-bearing aryl ring (after functionalization): DMAc, DMF, or dioxane/water are common.
Purification: normal-phase silica gel elutes with hexane/EtOAc or toluene/EtOAc; the ester typically increases Rf vs parent diaryl ketone.
Quick comparison (general):
DCM: fast, good solubility; volatile; halogenated waste.
EtOAc: greener, good eluent; may co-elute impurities of similar polarity.
THF/2-MeTHF: strong solvating power for organometallics; 2-MeTHF offers greener profile.
Always verify actual solubility/behavior with small-scale trials before scale-up.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Container: Store tightly closed in a clean, dry, inert container. Protect from moisture and prolonged light exposure to minimize potential photooxidation.
Stability considerations (general for aryl ketones/esters): typically stable at ambient conditions when dry and protected from strong acids/bases and oxidants. Avoid extended exposure to strong UV.
Solution handling:
Prepare stock solutions in dry, oxygen-free solvents if long-term solution storage is required. For routine use, freshly prepared solutions in DCM, THF, EtOAc, toluene, or MeCN are typical.
If preparing solutions for biological assays, DMSO or ethanol stocks are common; store at 2–8 °C for short term, or ≤−20 °C for longer term, in amber vials. Limit freeze–thaw cycles by aliquoting.
For definitive shelf-life, assay/purity retention, and any special handling instructions, consult the batch-specific CoA and SDS. For research use only (per Product Data).
Structure and Identity
Brief description: 3'-Carboethoxy-3-phenylpropiophenone is an aryl–alkyl ketone bearing two benzene rings separated by a three‑carbon chain (a 1,3-diaryl-1-propanone scaffold). One aryl ring contains a meta (3′) ethoxycarbonyl (carboethoxy, –CO2Et) substituent.
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 interpretation from the chemical name; literature/structure reasoning):
Core functional group: aromatic ketone (benzoyl) within a 1,3-diphenylpropanone framework.
Substituents: a second phenyl group at the 3-position of the propanone chain; the 3′-position of that phenyl carries an ethoxycarbonyl (–CO2CH2CH3) group (a deactivating, meta-directing ester).
Conjugation: the carbonyl is conjugated to one phenyl ring; limited cross‑conjugation along the benzylic chain; potential for intramolecular aryl–carbonyl interactions in certain conformers.
Stereochemistry: as named, the molecule is achiral overall (no stereogenic centers in the parent 1,3-diarylpropanone backbone). If generated via asymmetric routes, enantioenriched homologs could exist, but this listing does not indicate chirality.
2D depiction in words: Ph–CO–CH2–CH(Ph–3′‑CO2Et), with the right-hand ring bearing –CO2Et at its meta position relative to the benzylic attachment point.
Synthetic Utility
Key functional elements and their reactivity (general guidance for this scaffold):
Aryl ketone (benzoyl) center:
Enolization under base (LDA, NaHMDS, KOtBu) enables alpha‑functionalization (alkylation, aldol, Michael). Benzylic stabilization often allows lower temperatures and improved control over mono‑ vs di‑substitution.
Carbonyl transformations: reductions to secondary alcohols; Baeyer–Villiger oxidation to aryl acetates; formation of imines/oximes/hydrazones as protecting/derivatization handles.
Benzylic framework (1,3‑diarylpropanone):
Intramolecular cyclizations (Friedel–Crafts or aldol) deliver indanones, tetralones, or chalcone-like enones after appropriate activation (e.g., dehydration of aldol adducts).
Wittig/HWE olefination at the carbonyl provides conjugated enones useful for further Michael additions or heterocycle assembly.
Carboethoxy substituent on the distal aryl ring:
Synthetic handle: saponification to carboxylic acid, followed by amide coupling (HATU/EDC) or Curtius/Schmidt rearrangements from acyl azides under suitable conditions.
Electronic control: deactivates the ring toward EAS and directs meta. Cross‑coupling strategies typically require prior halogenation or directed metallation, then Pd‑catalyzed C–C/C–N formation.
Protecting-group considerations:
The ethyl ester is stable to mild bases and many nucleophiles but can transesterify under acidic/alcoholic conditions; choose conditions to preserve or deliberately exchange the ester.
Overall, the molecule offers orthogonal reactivity at the carbonyl, benzylic positions, and the ester-bearing aryl ring—valuable in multistep route design.
Target Specificity
Not applicable. This product is a small-molecule building block and is not an antibody, enzyme, or biological targeting reagent. No target, epitope, isotype, or species reactivity is associated with this item in the Product Data.
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