Ethyl 5-(2-fluorophenyl)-5-oxovalerate - ≥95% , CAS No.898753-35-0

CAS: 898753-35-0 Cat. No.: E947622 Formula: C₁₃H₁₅FO₃ Peso molecolare: 238.258 PubChem CID: 24727406

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifiche e purezza

≥95%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥95%

Nomi e identificatori

• Sorrisi canonici: CCOC(=O)CCCC(=O)C1=CC=CC=C1F
• IUPAC Name: ethyl 5-(2-fluorophenyl)-5-oxopentanoate
• InChIKey: JWDJUKXKHBKNFO-UHFFFAOYSA-N
• INCHI: 1S/C13H15FO3/c1-2-17-13(16)9-5-8-12(15)10-6-3-4-7-11(10)14/h3-4,6-7H,2,5,8-9H2,1H3
• Isomeri SMILES: CCOC(=O)CCCC(=O)C1=CC=CC=C1F
• PubChem CID: 24727406
• Peso molecolare: 238.258

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Classe Organooxygen compounds
      • Subclass Carbonyl compounds
        • Level5 Ketones
          • Level6 Aryl ketones
            • Level7 Phenylketones
              • Level8 Alkyl-phenylketones

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Classe: Organooxygen compounds
• Subclass: Carbonyl compounds
• Intermediate Tree Nodes: Ketones - Aryl ketones - Phenylketones
• Direct Parent: Alkyl-phenylketones
• Alternative Parents: Butyrophenones Benzoyl derivatives Aryl alkyl ketones Fluorobenzenes Fatty acid esters Aryl fluorides Vinylogous halides Carboxylic acid esters Monocarboxylic acids and derivatives Organofluorides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Alkyl-phenylketone - Butyrophenone - Benzoyl - Aryl alkyl ketone - Halobenzene - Fluorobenzene - Fatty acid ester - Aryl fluoride - Benzenoid - Fatty acyl - Aryl halide - Monocyclic benzene moiety - Vinylogous halide - Carboxylic acid ester - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Hydrocarbon derivative - Organic oxide - Organohalogen compound - Organofluoride - Aromatic homomonocyclic compound
• Descrizione: 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

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: 238.250 g/mol
• XLogP3: 2.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 238.101 Da
• Monoisotopic Mass: 238.101 Da
• Topological Polar Surface Area: 43.400 Ų
• Heavy Atom Count: 17
• Formal Charge: 0
• Complexity: 265.000
• 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 assay or immunoassay application protocols apply to this small-molecule building block. Typical laboratory use involves synthetic organic transformations as outlined in the Reaction & Applications and Reaction Conditions sections. For analytical verification, users commonly employ:

• NMR (1H, 13C; 19F NMR for the aryl fluorine) to confirm structure.
• IR to verify dual carbonyl features (distinct ester and ketone stretches).
• LC-MS/GC-MS for purity and mass confirmation, with UV detection benefiting from the aromatic ketone chromophore (general/literature).

Refer to your project-specific SOPs for reaction setup, workup, and purification procedures.

Biological Roles

This product is a synthetic organic intermediate with no known endogenous biological role.

• Not a natural metabolite or cofactor; no established participation in primary or secondary metabolic pathways (general/literature).
• Aryl ketoesters of this type are commonly used in medicinal chemistry programs as building blocks during target exploratory synthesis, SAR elaboration, and pro-fragment installation; however, such use is within research contexts only and does not imply biological activity of the reagent itself.
• The 2-fluorophenyl motif is frequently employed to modulate physicochemical properties (lipophilicity, metabolic stability) in candidate molecules; here it is anchored via a benzoyl linkage and separated from an ester terminus by a three-methylene spacer, offering a handle for conjugation or diversification (general observation in synthetic chemistry).

No medical, therapeutic, or diagnostic claims are made for this product. It is supplied strictly for research use only (per Product Data). For any biological testing or screening, users should establish their own safety and risk assessments and ensure compound purity and identity via analytical methods before use.

Buffer Applications

Not typically applicable. Ethyl 5-(2-fluorophenyl)-5-oxovalerate is a hydrophobic organic building block and is not used as a buffering agent. For experiments requiring this compound in aqueous environments, employ suitable co-solvents (e.g., DMSO, ethanol) and then dilute into buffered media as needed. Select the buffer based on the biological system, not on this reagent; verify compatibility to avoid hydrolysis under strongly basic or acidic conditions.

Green Alternatives

While the compound itself is a substrate, greener practices can be adopted in its use, focusing on solvent choice, reagent selection, and energy efficiency (general/literature guidance).

• Prefer greener solvents where feasible:

  • Replace DCM/chloroform with ethyl acetate, 2-methyltetrahydrofuran (2-MeTHF), cyclopentyl methyl ether (CPME), or toluene, depending on reaction needs.
  • Use acetonitrile judiciously; where possible, ethanol or isopropanol can serve as greener polar solvents for some reductions or coupling steps.

• Reagent alternatives:

  • Reduce reliance on pyrophoric bases (LDA/NaHMDS) by using carbonate/alkoxide bases under phase-transfer conditions when selectivity allows.
  • For reductions, prefer catalytic hydrogenation (H2/Pd, H2/Ni) or transfer hydrogenation (e.g., formate-based) over stoichiometric metal hydrides, where compatible.

• Process intensification:

  • Employ flow chemistry for hazardous steps (cryogenic enolate generation, acyl chloride formation) to improve safety and reduce solvent inventory.
  • Optimize to room-temperature conditions and higher concentrations to cut energy and solvent use.

• Small comparison (general):

  • DCM vs 2-MeTHF: similar solvency for ketoesters; 2-MeTHF is biorenewable, higher boiling (reduces VOC emissions) but can retain water—ensure adequate drying.
  • THF vs CPME: CPME shows low peroxide formation tendency and good hydrophobicity; THF is widely compatible but tends to form peroxides and often requires inhibitor checks.

Waste management: segregate halogenated from non-halogenated streams; recover/recycle EtOAc/MeTHF where infrastructure exists.

Pharmaceutical Uses

• Formulation/excipient role: None. This product is not an excipient and is not intended for incorporation into finished dosage forms.
• Typical context (general/literature): Employed as a synthetic intermediate in medicinal chemistry and process research to build aryl-alkyl frameworks containing both ketone and carboxylate-derived functionalities. The ortho-fluoro aryl ketone can influence conformation and electronics, and the terminal ester enables late-stage diversification (e.g., amidation, hydrolysis to acids for salt screening) at the research stage.
• Pharmacopeia/compendial status: Not a compendial article.
• Regulatory note: Research use only (per Product Data). Any use in cGMP or pharmaceutical manufacturing would require independent qualification, specifications, and impurity controls determined by the user.

When using as an API intermediate or impurity standard in research settings, confirm identity/purity via orthogonal analyses (NMR, LC-MS, HRMS) and document traceability to the CoA. Avoid claims of therapeutic effect; this material is not approved for human or veterinary applications.

Physical Properties

Item-specific physical constants are not provided in the Product Data. Do not use numerical values on specifications without consulting the lot-specific CoA/SDS.

• Appearance (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point: Not specified for this item; refer to CoA/Spec Sheet. (Aryl aliphatic ketoesters of similar size are typically liquids at ambient temperature and may distill under reduced pressure; literature, general.)
• Melting point: Not specified for this item; refer to CoA/Spec Sheet.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (general/literature):
  • Low solubility in water; miscible with common organic solvents such as dichloromethane, chloroform, THF, ethyl acetate, toluene, and acetonitrile.
  • Partitioning expected to favor organic phase in liquid–liquid separations (literature, general behavior of aryl ketoesters).
• Vapor pressure/volatility: Typically low at ambient temperature for compounds of this molecular class (literature, general).
• Spectral characteristics (general):
  • IR: strong C=O stretches for ketone (~1680–1715 cm⁻¹) and ester (~1735–1750 cm⁻¹); aromatic C–F stretch typically ~1000–1100 cm⁻¹ (literature).
  • 1H NMR: two different α-CH2 groups (to ketone and to ester) typically downfield relative to internal methylenes; aromatic multiplets with characteristic o-F coupling patterns (literature).

For binding specifications (water content, residual solvents, metals, UV cutoff, etc.): Not specified for this item; refer to CoA/Spec Sheet.

Quality and Grades

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

• Interpreting grade (general guidance):

  • If supplied as synthetic/intermediate grade: appropriate for research-scale synthesis and method development.
  • If HPLC or LC-MS grade were specified (not provided here), such grades would emphasize low UV background and minimal nonvolatile residues, beneficial for analytical use. In absence of such a designation, treat as a research chemical intended for preparative/synthetic applications.

• Stabilizers and additives: Not specified for this item; refer to CoA/Spec Sheet. Ketoesters typically do not require inhibitors; however, adventitious acid/base can promote side reactions. Neutral, dry storage minimizes degradation (general/literature).

• What to check on receipt (best practice):

  • Verify identity by NMR/IR and, if applicable, GC/LC-MS.
  • Review CoA for assay (%), water (KF), and residual solvent content when available.
  • Inspect for discoloration or particulate matter; ketoesters often are colorless to pale liquids or low-melting solids (general) but the appearance for this specific item is not specified here.

• Regulatory/usage note: Research use only (per Product Data). Not for human or veterinary use.

Reaction and Applications

As an aryl–aliphatic ketoester, Ethyl 5-(2-fluorophenyl)-5-oxovalerate offers two orthogonal carbonyl handles and two distinct α-positions, enabling diverse synthetic transformations (general/literature guidance):

• Enolate chemistry (ketone vs ester):

  • The methylene α to the benzoyl group (ArCO–CH2–) is typically more acidic than the methylene α to the ester. Using LDA or NaHMDS at −78 to −20 °C in THF can provide kinetic control at the ketone α-position; stronger bases/chelation or stepwise protection can target the ester α-site.
  • Subsequent alkylation, acylation, or aldol additions furnish elaborated frameworks.

• Functional group interconversions:

  • Ester: hydrolysis to the carboxylic acid (saponification), conversion to acid chloride (oxalyl chloride, SOCl2), amide coupling (EDC/HATU/peptide coupling), or reduction to primary alcohols (LiAlH4) or aldehydes (DIBAL-H, −78 °C).
  • Ketone: formation of oximes/hydrazones, reductive amination, selective reduction to secondary alcohols (NaBH4, MeOH; or catalytic hydrogenation).

• Ring construction and tether strategies:

  • Intramolecular condensations (Dieckmann/Claisen variants) after appropriate derivatization can form cyclic ketones/esters.
  • Michael-type additions if the substrate is converted to an enone; conversely, the ketoester can serve as a nucleophile in conjugate additions to enones.

• Cross-coupling on the aryl ring: The 2-fluoro substituent is relatively inert but can participate in SNAr with strongly activated nucleophiles or be leveraged for subsequent regioselective metalation (e.g., ortho-lithiation adjacent to fluorine; literature) to introduce further functionality.

Use dry, oxygen-free conditions for strong-base enolate work; quench carefully to maintain chemoselectivity.

Reaction Conditions

General, literature-derived guidance for typical manipulations of aryl–aliphatic ketoesters. Always optimize for your specific substrate and consult primary literature.

• Enolate formation/alkylation:

  • Base: LDA or NaHMDS (1.1–1.5 equiv) in dry THF, −78 to −40 °C; add electrophile (alkyl halide, acyl chloride) at low temperature, then warm to 0–25 °C. Kinetic control generally favors deprotonation α to the benzoyl group. Typical reaction times 0.5–3 h after electrophile addition; isolated yields often 50–85% depending on electrophile.
  • Alternative: K2CO3/DMF or Cs2CO3/MeCN for milder α-functionalization adjacent to the ester, especially with activated electrophiles.

• Ester transformations:

  • Saponification: NaOH or KOH (1–2 M aqueous), EtOH/H2O, 0–25 °C, 1–4 h; acidify to pH ~1–2, extract with EtOAc.
  • Amidation: HATU or EDCI coupling in DMF or DCM with amine base (DIPEA), 0–25 °C, 1–16 h.
  • Reduction: DIBAL-H (1.1–1.5 equiv) in toluene/CH2Cl2 at −78 °C to aldehyde; LiAlH4 (excess) in THF reflux to primary alcohol.

• Ketone manipulations:

  • NaBH4 (1–2 equiv) in MeOH/EtOH, 0–25 °C, 0.5–2 h to secondary alcohol (often chemoselective vs ester).
  • Reductive amination: amine, NaBH3CN or H2/Pd, pH-controlled solvent (MeOH/AcOH), 0–25 °C.

• Aryl functionalization (advanced):

  • Directed ortho-metalation adjacent to F with s-BuLi/TMEDA at −78 °C (strictly anhydrous); quench with electrophiles (CO2, aldehydes) as compatible with the tethered ketoester.

• Workup/purification:

  • Quench strong bases at low temperature with saturated NH4Cl; extract into EtOAc/DCM; dry (Na2SO4). Silica gel chromatography using hexanes/EtOAc or toluene/EtOAc.

All temperatures and times are general literature guidance and should be experimentally validated.

Safety and Handling

• GHS classification, signal word, pictograms, and H-statements: Not specified for this item; refer to the SDS for authoritative safety information.
• General hazards (literature/general for aryl ketoesters):
  • May cause skin and eye irritation; avoid inhalation of vapors/aerosols and contact with skin or eyes.
  • Combustible organic liquid; keep away from ignition sources and hot surfaces.
• Personal protective equipment (PPE):
  • Lab coat, safety glasses or chemical splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood to control vapors and to prevent exposure.
• Handling guidance:
  • Avoid strong bases and strong acids that may induce hydrolysis, condensation, or decomposition.
  • Avoid strong oxidizers and reducing agents that may react with the ketone or ester functionalities.
  • Cap promptly after use to minimize moisture uptake and to prevent contamination.
• First-aid overview (consult SDS for full instructions):
  • Skin: Wash with soap and water. Remove contaminated clothing.
  • Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present and easy to do.
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Spill/leak response:
  • Absorb with inert material (vermiculite, sand), collect for disposal. Ventilate area. Eliminate ignition sources.
• Fire-fighting measures:
  • Use alcohol-resistant foam, dry chemical, or CO2. Cool containers with water spray.

Always defer to the product SDS and institutional EHS policies for risk assessment and controls.

Solvent Selection

This product is a functionalized building block rather than a solvent. Solvent selection pertains to dissolving it for reactions, extractions, and purification.

• Polarity/solubility profile (general/literature):

  • Readily soluble in medium-polarity organic solvents: dichloromethane (DCM), chloroform, ethyl acetate (EtOAc), tetrahydrofuran (THF), acetonitrile (MeCN), and toluene.
  • Poorly soluble in water; partitions strongly into organic phases during workups.

• Typical choices by operation:

  • Reaction media: DCM or toluene for electrophilic/aromatic-compatible steps; THF or MeTHF for base-mediated enolate chemistry; MeCN for SN2/phase-transfer conditions.
  • Workup/extraction: EtOAc/MTBE/hexanes combinations; brine washes help break emulsions.
  • Chromatography: Silica gel with hexanes/EtOAc or toluene/EtOAc gradients. The aryl ketone often shows moderate UV absorbance at 254 nm, aiding detection (general/literature).

• Comparison notes:

  • THF vs 2-MeTHF: similar solubilizing power; 2-MeTHF offers greener credentials and higher hydrophobicity, which can aid separations.
  • DCM vs EtOAc: DCM provides stronger elution and higher solvating power; EtOAc is a greener alternative but may require larger volumes/longer times.

Select solvents based on reaction mechanism (e.g., enolate generation benefits from aprotic ethers) and downstream environmental/ESG priorities.

Storage and Reconstitution

• Storage conditions (item-specific): Room temperature (per Product Data). Store tightly closed in a dry, well-ventilated area.
• Container recommendations: Keep in amber glass if long-term storage is anticipated to minimize potential photochemical degradation of the aryl ketone (general). Use PTFE-lined caps to reduce permeation.
• Inert atmosphere: Not strictly required for most handling; however, storing under nitrogen/argon is good practice for moisture- and base-sensitive ketoesters (general/literature).
• Incompatibilities: Avoid strong acids/bases (can induce hydrolysis/condensation), strong oxidizers/reductants, and prolonged exposure to moisture.
• Reconstitution/Preparation for use: If solidified or viscous, warm gently to ambient and dissolve in a suitable dry solvent (e.g., DCM, THF, EtOAc, toluene, MeCN) to the desired concentration. For aqueous systems, prepare a concentrated stock in DMSO or ethanol, then dilute into buffer immediately before use; verify stability against hydrolysis under chosen pH.
• Freeze–thaw: Typically unnecessary at room-temperature storage; if cold storage is chosen for extended periods, minimize freeze–thaw cycles by aliquoting.
• Stability monitoring: Periodically check by TLC/LC for signs of hydrolysis (appearance of acid/alcohol) or reduction/oxidation products if stored for extended durations.

Research use only (per Product Data). Refer to the CoA/SDS for any lot-specific handling and stability details.

Structure and Identity

Ethyl 5-(2-fluorophenyl)-5-oxovalerate is a bifunctional aryl–aliphatic ketoester useful as a synthetic building block.

• Item-specific identifiers (Product Data)

  • SKU: E947622
  • Product name: Ethyl 5-(2-fluorophenyl)-5-oxovalerate
  • CAS: 898753-35-0
  • CID: 24727406
  • InChIKey: 171695 (as provided); full standardized InChIKey not specified for this item
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Molecular formula and weight

  • 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/literature description)

  • Functional groups: one aryl ketone (benzoyl) and one ethyl ester on a pentyl chain (ethoxycarbonyl–(CH2)3–CO–aryl).
  • Aryl substituent: 2-fluorophenyl directly bonded to the ketone carbonyl (o-fluorobenzoyl moiety).
  • 2D structure in words: an ethyl ester carbonyl connected to a three-methylene spacer that terminates at a benzoyl carbonyl attached to a 2-fluorophenyl ring (i.e., ethyl 4-(2-fluorobenzoyl)butyrate).
  • Stereochemistry: none (acyclic, no stereogenic centers).

• Notes

  • The compound presents two distinct α-positions (adjacent to the ketone and to the ester), enabling differentiated enolate chemistry.
  • The o-fluoro substituent is an ortho-directing, deactivating ring substituent that can influence reactivity and NMR characteristics (literature).

Synthetic Utility

Ethyl 5-(2-fluorophenyl)-5-oxovalerate provides complementary reactivity at two carbonyl termini and at both α-positions, enabling convergent and divergent routes (general/literature guidance):

• Carbonyl toolbox:

  • Ketone: amenable to oxime/hydrazone formation, reductive amination, and stereoselective reductions (CBS, chiral transfer hydrogenation) to give benzylic secondary alcohols.
  • Ester: convertible to acid, acid chloride, amide, hydroxamic acid, or alcohol/aldehyde (DIBAL-H) without perturbing the aryl ketone under controlled conditions.

• Enolate differentiation:

  • Regioselective deprotonation near the benzoyl moiety often favored under kinetic conditions (LDA/THF, −78 to −40 °C). Thermodynamic control or use of weaker bases/chelation can bias the ester α-site. Subsequent electrophile capture installs substituents remote from the aryl ring.

• Tether-enabled cyclizations:

  • After suitable activation, intramolecular condensations can build five- or six-membered carbocycles or lactones (e.g., Dieckmann-type if the ester end is converted appropriately), furnishing motifs relevant to fragrance, materials, or lead-like scaffolds.

• Aryl fluorine as a handle:

  • Ortho-fluorine can direct lithiation for further aryl elaboration (e.g., metal–halogen exchange adjacent to F followed by electrophile trapping; literature), enabling late-stage diversification of the aryl domain while retaining the aliphatic ketoester.

• Protecting-group orthogonality: The ester and ketone can be chemoselectively protected (e.g., ketalization, conversion to Weinreb amide) to choreograph multi-step sequences.

Target Specificity

Not applicable. This product is a small-molecule organic building block and is not an antibody, protein, or affinity reagent. No target, epitope, clone, isotype, or species reactivity information applies.