This compound belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
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
331.200 g/mol
XLogP3
4.800
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
10
Exact Mass
330.079 Da
Monoisotopic Mass
330.079 Da
Topological Polar Surface Area
43.400 Ų
Heavy Atom Count
21
Formal Charge
0
Complexity
333.000
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
No application protocols are specified in the Product Data for this small-molecule building block.
General lab-use suggestions (informational):
Preparation of stock solutions: Dissolve to 10–100 mM in dry DMSO, THF, EtOAc, or ethanol. Filter through 0.22 µm PTFE if needed.
Typical analytical QC: Record 1H/13C NMR (observe two C=O signals and diagnostic 2,5-dichloroaryl pattern), IR (ester and ketone C=O), and HRMS. For purity, use HPLC with UV detection at 254–280 nm.
Workup/purification: Silica gel chromatography with hexanes/EtOAc gradients; include 0.1–1% Et3N if adsorption/tailing of enolizable species is observed.
For any specialized application, develop and validate a protocol tailored to your reaction scheme and detection method.
Biological Roles
This compound is a synthetic aryl–aliphatic keto ester building block and is not known to occur in biological systems.
General context (literature/biochemistry)
Structural features (aryl ketone and ester) are common motifs in medicinal chemistry scaffolds, but this exact 2,5-dichloro-substituted 1,7-dicarbonyl framework has no established endogenous role or metabolic function.
If used in biological assays, it would typically serve as a synthetic intermediate or as a probe precursor rather than an active biochemical entity. Metabolic liabilities would be expected at the ester (hydrolysis by esterases) and at the aryl ketone (reduction or conjugation), consistent with general xenobiotic transformations.
Practical guidance
For any in vitro studies, prepare fresh solutions in DMSO or EtOH and dilute into media with care to avoid precipitation. Assess nonspecific binding to plastics or serum proteins due to high hydrophobicity.
No specific biological targets, pathways, or activities are claimed or implied for this product. Use is limited to research applications per Product Data (Research Use Only).
Buffer Applications
Not typically applicable. As a hydrophobic organic building block with poor water solubility, this compound is not used to prepare aqueous buffer systems.
Practical notes for labs handling it alongside buffers:
Prepare concentrated stock solutions in DMSO, EtOH, or THF and add to buffered systems with vigorous mixing to avoid precipitation (final cosolvent usually kept ≤1–2% v/v in biochemical assays, if applicable).
If hydrolysis studies are intended, standard buffers (e.g., phosphate pH 7.4, carbonate pH 10) can be used to model ester stability, but the compound itself is not a buffering agent.
Green Alternatives
While the reagent itself is a specialty building block, greener choices can often be made in the solvents and conditions used with it. Below are practical substitutions and trade-offs (literature-based guidance):
Solvent substitutions
Replace DCM/chloroform with EtOAc or dimethyl carbonate (DMC) for extractions and chromatography where feasible; both are less toxic and more sustainable.
Use 2-MeTHF or CPME instead of THF for enolate chemistry; they are derived from renewable resources (2-MeTHF) and simplify aqueous workups due to lower water miscibility.
Prefer toluene or anisole over benzene for aromatic-compatible reactions.
Bases and reducing agents
Consider K2CO3 or DBU in green solvents for mild transesterifications instead of strong mineral acids. For selective ketone reduction, NaBH(OAc)3 in EtOAc or ethanol can be milder and safer than pyrophoric hydrides.
Energy and workup
Conduct reactions at ambient temperature when possible; apply flow or microwave selectively to reduce time/energy. Optimize crystallization or precipitation workups to minimize halogenated waste.
Comparison snapshot (general)
THF vs 2-MeTHF: similar performance for enolates; 2-MeTHF is bio-based and eases phase separation, but can have broader peroxides specification—monitor and test.
DCM vs EtOAc: DCM offers superior volatility and elution but is a halogenated solvent with higher environmental impact; EtOAc is greener but may require longer evaporation times and higher eluent polarity.
Note: Always validate alternative solvents for solubility and selectivity with this specific substrate.
Pharmaceutical Uses
No pharmacopeial grade or excipient role is specified for this item; it is provided for research use only.
General formulation context (literature-based):
Structural class relevance: Aryl ketone–esters can serve as intermediates en route to candidate APIs (e.g., via amidation, reduction, or cyclization). However, this product is not supplied as a drug substance or excipient.
Preformulation considerations: High hydrophobicity suggests the need for nonaqueous vehicles (EtOH, PEG 400) or lipid-based systems if used as an intermediate in preclinical enabling chemistry; the ester can be hydrolyzed to the corresponding acid for salt formation during lead optimization.
Regulatory note: In the absence of pharmacopeial monographs or GMP designation, material should not be used in human or veterinary applications. For any development work, resynthesis under GMP and full impurity profiling would be required.
Item-specific status
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Pharmacopeia listings: None indicated.
Intended use: Research and laboratory synthesis only.
Physical Properties
Item-specific specifications are not provided in the Product Data; consult the CoA/Spec Sheet for lot-specific values. The following values are general expectations inferred from structure and literature/computational estimation—use for planning only, not as product specifications.
Appearance (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: ~331.24 g/mol (literature/computed from C16H20Cl2O3).
Physical state: Likely low-melting solid or viscous oil (literature expectation for analogous aryl-alkyl keto esters of similar MW); verify per CoA.
Boiling point: Typically decomposes or distills under reduced pressure; exact BP not established for this specific compound (literature: aryl keto esters in the 300–350 °C range at 1 atm often distill at 120–180 °C under 0.1–5 mmHg).
Melting point: Not found in common references for this exact structure.
Density: Not specified for this item; refer to CoA/Spec Sheet. (Literature expectation for chlorinated aryl keto esters: ~1.20–1.30 g/mL at 20–25 °C.)
Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
LogP (octanol/water): Expected high hydrophobicity (literature estimate logP ~3–5) due to aryl dichloro ring and aliphatic chain.
Solubility (qualitative, literature): High in nonpolar/aprotic organics (DCM, CHCl3, toluene, EtOAc, THF); low in water; moderate in alcohols.
UV-vis: Aromatic chromophore with typical π–π* absorption in near-UV (literature: λmax ~230–280 nm depending on solvent); no item-specific UV cutoff provided.
Always confirm critical method parameters (e.g., RI, density) experimentally for this item/lot.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizer/additives: Not specified for this item; refer to CoA/Spec Sheet.
How to interpret and apply quality information (context for this compound type):
Research-use reagent: This listing is intended for research and laboratory applications only (per Product Data: Research Use Only). Absent pharmacopeial grading, material is typically suitable for synthesis, method development, and structure–activity studies.
If “>95%” or higher purity is provided on the CoA: This is generally adequate for most synthetic transformations (e.g., enolate chemistry, reductions, couplings). For photophysical or kinetic studies, consider additional purification (flash chromatography, recrystallization) to remove trace acid/base that could catalyze side reactions (e.g., self-condensation, transesterification).
UV/LCMS suitability: In the absence of designated “HPLC grade” or “LC-MS grade,” expect typical organic impurities. If low background absorbance or MS cleanliness is critical, pre-test blank solvent extracts of the solid or perform minor pre-purification.
Residual solvents/trace metals: Not specified for this item; refer to CoA/Spec Sheet. These are normally low for small-molecule organics prepared by standard routes, but verify if sensitive downstream chemistry (e.g., base-catalyzed cyclizations) is planned.
Lot-to-lot verification: For building blocks like aryl keto esters, confirm identity by 1H/13C NMR (diagnostic aryl signals and two carbonyl carbons), IR (two C=O stretches), and HRMS.
Reaction and Applications
As an ethyl 1,7-dicarbonyl equivalent bearing an aryl ketone, this compound is a versatile building block for C–C and C–X bond-forming chemistry and heterocycle synthesis.
Enolate chemistry and alkylations
The methylenes α to the ketone (C7) and ester (C2) are enolizable. Under LDA or NaHMDS at −78 to 0 °C (THF), selective deprotonation adjacent to the ketone is typically favored; HMPA or mixed solvents can be used to tune selectivity (literature guidance).
Alkylation of the ketone-derived enolate enables installation of side chains prior to downstream cyclizations or reductions.
Reductive transformations
NaBH4 or NaBH(OAc)3 can reduce the aryl ketone to a secondary alcohol while leaving the ester intact (solvent-controlled chemoselectivity). Stronger hydride (LiAlH4) reduces both carbonyls to diols/alcohols.
Wolff–Kishner or Clemmensen protocols can convert the aryl ketone to a methylene, yielding an aryl-alkyl chain with a terminal ester.
Functional group interconversions
Saponification to the corresponding acid (EtOH/H2O, NaOH) followed by amide coupling (EDC/HOBt or HATU) furnishes amides retaining the distal aryl ketone.
Transesterification (ROH, acid/base catalysis) to tune protecting group stability.
Cyclizations and ring construction
Intramolecular aldol/Dieckmann-type closures are accessible after suitable α-functionalization, enabling cyclohexanone- or lactone-type frameworks fused or tethered to a 2,5-dichlorophenyl unit.
Late-stage diversification
The 2,5-dichloro pattern supports cross-coupling (Suzuki, Buchwald–Hartwig) after conversion to the corresponding aryl boronate/amine partners, enabling rapid SAR around a preserved 1,7-dicarbonyl backbone (via selective activation at aryl–Cl under Pd catalysis, literature precedent).
Reaction Conditions
General literature-guided conditions for transformations of aryl keto esters like Ethyl 8-(2,5-dichlorophenyl)-8-oxooctanoate (use as starting points; optimize for this substrate):
Enolate formation and alkylation
Base: LDA or NaHMDS (1.1–1.5 equiv) in dry THF or 2-MeTHF.
Temperature: −78 to 0 °C for selectivity; warm to rt after electrophile addition.
NaBH4 (1–2 equiv) in MeOH, EtOH, or i-PrOH at 0–25 °C; monitor by TLC/LC-MS. Alternatively, NaBH(OAc)3 in DCE/EtOAc with AcOH for milder conditions.
Global reduction (ketone and ester)
LiAlH4 (2–4 equiv) in dry THF/diethyl ether at 0 °C to reflux; slow addition and strict anhydrous conditions. Quench cautiously.
Saponification to acid
NaOH or KOH (1–2 M) in EtOH/H2O (1:1) at rt to 60 °C, 1–6 h, then acidify to pH ~2 and extract with EtOAc.
Transesterification
ROH solvent with catalytic acid (p-TsOH) or base (NaOMe/ROH), rt–reflux, removing alcohol byproduct or using Dean–Stark as needed.
Cross-coupling on aryl chloride (after appropriate protection/sequence planning)
Suzuki–Miyaura: Pd(dppf)Cl2 (1–3 mol%), base (K3PO4 or K2CO3), 2-MeTHF/H2O or dioxane/H2O, 60–100 °C.
Buchwald–Hartwig amination: Pd2(dba)3 (1–2 mol%) with BrettPhos or XPhos ligand, NaOtBu, toluene/tert-amyl alcohol, 80–110 °C.
Yields and selectivities vary with substituents and conditions; confirm by small-scale trials and analytical monitoring.
Safety and Handling
Item-specific hazard classification data (signal word, pictograms, GHS classes, H-statements) are not provided; defer to the official SDS for authoritative information.
General laboratory safety guidance for aryl–aliphatic keto esters (informational):
Anticipated hazards: May cause skin/eye irritation and respiratory tract irritation upon dust/vapor/aerosol exposure; avoid ingestion and inhalation. Aromatic ketones can be photosensitizers; minimize UV exposure of bulk material and solutions.
PPE: Wear lab coat, safety glasses or splash goggles, and appropriate nitrile gloves. Use in a fume hood to limit vapor/solvent exposure during handling and transfer.
Handling: Avoid prolonged exposure to light and heat. Prevent contact with strong bases (enolate formation) unless intended, and with strong oxidizers or reducing agents that may affect carbonyl groups or the aryl ring.
Incompatibilities (general): Strong bases and nucleophiles (can induce transesterification, saponification, or aldol-type reactions); strong acids (acid-catalyzed hydrolysis); potent oxidizers.
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 attention if irritation persists. Inhalation: move to fresh air and monitor for symptoms. Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Fire safety: Use CO2, dry chemical, or foam. Combustion may produce HCl and other irritating fumes due to chlorinated aromatic content.
Storage per Product Data: Room temperature. Keep container tightly closed, dry, and protected from light. Always consult the SDS for the specific lot before use.
Solvent Selection
This hydrophobic aryl–aliphatic keto ester dissolves readily in common organic solvents. Select solvents based on the operation (dissolution, reaction, purification):
Moderately soluble: MeOH, i-PrOH, acetonitrile (varies with temperature).
Practically insoluble: Water and aqueous buffers at neutral pH.
Choosing solvents by task
Reaction medium for enolate chemistry: Anhydrous THF, 2-MeTHF, or toluene/THF mixtures under inert atmosphere to control base strength and temperature.
Reductions (ketone to alcohol): Alcoholic solvents (MeOH, i-PrOH) with borohydrides; or EtOH/THF with NaBH(OAc)3 for chemoselective transformations if compatible with ester.
Hydrolysis/transesterification: MeOH or EtOH with catalytic acid/base as appropriate; for saponification, aqueous MeOH/THF enhances phase homogeneity.
Chromatography: Normal-phase silica using hexanes/EtOAc or toluene/EtOAc. Aromatic ring and dual carbonyls give moderate Rf in 20–40% EtOAc/hexanes; adjust with 1–5% MeOH if tailing occurs.
Small comparison (literature-based)
THF vs 2-MeTHF: Similar solvating power for enolates; 2-MeTHF offers greener profile and easier water separation. THF is more miscible with water, aiding extractions but complicating workups.
DCM vs EtOAc: DCM provides stronger elution and low viscosity; EtOAc is less toxic and bio-based but more polar—can increase co-elution of polar impurities.
Storage and Reconstitution
Storage conditions (item-specific): Room temperature (per Product Data). Store in a tightly closed container in a dry place, protected from light. For long-term stability, many labs prefer 2–8 °C to minimize slow hydrolysis/oxidation, but this is not mandated by the 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.
Reconstitution and handling (general guidance):
Solubility: Readily soluble in common organic solvents (DCM, THF, EtOAc, toluene, alcohols); insoluble in water (literature expectations).
Preparing solutions: Use anhydrous solvents for base-sensitive operations. For analytical stocks, prepare 10–100 mM in dry acetonitrile, DMSO, or ethanol. Mix thoroughly to ensure homogeneity; warm gently if needed.
Stability in solution: Ester and ketone are moisture- and base-sensitive. Avoid prolonged exposure to strong acids/bases; minimize time in protic solvents if base is present.
Freeze–thaw: Not typically applicable unless stored as solution. If freezing solutions, aliquot to avoid repeated freeze–thaw; store at −20 °C in airtight vials.
Container compatibility: Use amber glass vials with PTFE-lined caps to reduce adsorption and protect from light.
Always consult the CoA/SDS for lot-specific guidance. Product is for research use only.
Structure and Identity
Ethyl 8-(2,5-dichlorophenyl)-8-oxooctanoate is a bifunctional aryl–aliphatic 1,7-dicarbonyl ester featuring a distal aryl ketone and a terminal ethyl ester.
Item-specific identifiers (Product Data)
SKU: E936457
CAS: 898778-20-6
PubChem CID: 24727536
InChIKey: 266304 (as provided)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Computed/literature structural data (informational)
Proposed molecular formula (from name analysis): C16H20Cl2O3 (literature/computed)
Core scaffold: an eight-carbon chain bearing an ethyl carboxylate at C1 and an aryl ketone at C8.
Aryl substituent: 2,5-dichlorophenyl group bonded to the ketone carbonyl carbon (ipso position), ring chlorines at the 2- and 5-positions, leaving three ring hydrogens.
Functional groups: one ethyl ester (–CO2Et) and one aryl–alkyl ketone (–CO–Ar); multiple acidic α-C–H sites flanking each carbonyl.
2D structure (described): EtO2C–CH2–CH2–CH2–CH2–CH2–CH2–C(=O)–C6H3Cl2(2,5). The chain is linear, terminating at a benzoyl-type carbonyl directly attached to a 2,5-dichlorophenyl ring; the other terminus is an ethyl ester.
Stereochemistry: None (acyclic, no stereocenters implied by the name).
Notes: Structural and formula details above are provided as literature/computed context to aid method planning; consult primary spectral/analytical data (CoA/NMR/MS) for definitive identity confirmation for this specific lot.
Synthetic Utility
Key functional elements enable diverse downstream chemistry:
Dual carbonyl reactivity
Ketone site: Enolate formation (LDA/NaHMDS) enables α-functionalization (alkylation, aldol). Nucleophiles like NaBH4 or organometallics (RMgX, R2CuLi under controlled conditions) add to the ketone; chemoselectivity over the ester is tunable by reagent and temperature.
Ester site: Hydrolysis to the acid enables amide coupling (EDC/HATU), Curtius rearrangement (via acyl azide) to isocyanates/carbamates, or conversion to Weinreb amide for controlled acylations.
Strategic disconnections
Retrosynthetically, the molecule can arise from acylation of a 2,5-dichloroaryl lithium/cuprate with an ω-ester acylating agent or via Friedel–Crafts acylation of 2,5-dichlorobenzene derivatives with an 8-oxo acyl chloride equivalent (with directing concerns). Alternatively, Claisen condensation variants from ethyl adipate homologs and 2,5-dichlorobenzoyl chloride can assemble the 1,7-dicarbonyl.
Diversification of aryl ring
Two aryl chlorides enable Pd-catalyzed cross-couplings (Suzuki–Miyaura, Buchwald–Hartwig) to install (hetero)aryl or amine groups after or before manipulating the aliphatic chain, allowing SAR libraries while retaining the dicarbonyl backbone.
Cyclizations
After α-functionalization, intramolecular aldol/Dieckmann-type closures can yield cyclic ketones/lactones tethered to the aryl unit. Baeyer–Villiger oxidation of the aryl ketone offers ring-expanded/aromatic acetate motifs.
Overall, the substrate acts as a robust, chemoselectivity-rich handle set for stepwise elaboration toward complex small molecules.
Target Specificity
Not applicable. This product is a small-molecule organic building block, not a biological macromolecule or affinity reagent.
No antigen/epitope, clone, isotype, or species reactivity data are relevant.
For biochemical experiments, any “specificity” arises from the design of the assay or downstream derivatives synthesized from this scaffold, not from inherent target binding attributes of the reagent itself.
Domande frequenti
How should this product be stored?
Store at room temperature.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 898778-20-6, the molecular formula is C16H20Cl2O3, and the molecular weight is 331.23 g/mol. InChIKey OSORFDBMXOTXQS-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.
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