Ethyl 8-(2,3-dichlorophenyl)-8-oxooctanoate , CAS No.898777-93-0

CAS: 898777-93-0 Cat. No.: E947631 Formula: C₁₆H₂₀Cl₂O₃ Peso molecolare: 331.23 PubChem CID: 24727526

Storage

Room temperature

Specifications

Condizioni di conservazione di stoccaggio

Room temperature

Nomi e identificatori

• Sorrisi canonici: CCOC(=O)CCCCCCC(=O)C1=C(C(=CC=C1)Cl)Cl
• IUPAC Name: ethyl 8-(2,3-dichlorophenyl)-8-oxooctanoate
• InChIKey: GANNSLPPFDIBRT-UHFFFAOYSA-N
• INCHI: 1S/C16H20Cl2O3/c1-2-21-15(20)11-6-4-3-5-10-14(19)12-8-7-9-13(17)16(12)18/h7-9H,2-6,10-11H2,1H3
• Isomeri SMILES: CCOC(=O)CCCCCCC(=O)C1=C(C(=CC=C1)Cl)Cl
• PubChem CID: 24727526
• Peso molecolare: 331.23

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 Dichlorobenzenes Benzoyl derivatives Aryl alkyl ketones Fatty acid esters Aryl chlorides Vinylogous halides Carboxylic acid esters Monocarboxylic acids and derivatives Organochlorides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Alkyl-phenylketone - Butyrophenone - Benzoyl - 1,2-dichlorobenzene - Aryl alkyl ketone - Halobenzene - Fatty acid ester - Chlorobenzene - Aryl halide - Benzenoid - Fatty acyl - Monocyclic benzene moiety - Aryl chloride - Vinylogous halide - Carboxylic acid ester - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Hydrocarbon derivative - Organohalogen compound - Organic oxide - Organochloride - 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: 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

Application Protocols

No biological assay protocols are specified for this item. As a chemical building block, typical “application protocols” correspond to synthetic procedures.

• Item-specific tested applications: Not specified for this item.

• General laboratory handling

  • Verify identity and purity upon receipt (e.g., 1H/13C NMR, LC/MS).
  • For reaction setup, dry solvents and glassware if engaging in base-sensitive or enolate chemistry; exclude moisture for organometallic steps.
  • Employ standard inert-atmosphere techniques where strong bases or moisture-sensitive reagents are used.

Consult the literature or your internal SOPs for reaction-specific protocols.

Biological Roles

This product is offered for research use as a synthetic intermediate. It is not intended for biological assays as an active agent.

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

• General notes (literature context; not product-specific claims)

  • Aryl–aliphatic keto esters of this type are commonly used as inert intermediates in medicinal chemistry campaigns to construct analog libraries. Any “biological role” arises only after further transformation into target compounds.
  • The 2,3-dichlorophenyl ring is electron-withdrawing/deactivating; its presence can modulate lipophilicity and metabolic stability when incorporated into final molecules. These are design considerations rather than inherent biological activity of the intermediate.

No clinical or therapeutic uses are claimed or implied. For any in vitro testing, evaluate purity, residual solvents, and vehicle compatibility independently.

Buffer Applications

Not typically applicable. This compound is a hydrophobic organic intermediate and is not used to prepare aqueous buffer systems.

• If dissolution into assay media is required (general guidance), co-solvents such as DMSO or EtOH may be used in small percentages, but this is outside the typical use of this building block and should be validated for your assay.

Item-specific buffer relevance and recipes: Not specified for this item.

Green Alternatives

While the compound itself is a building block (not a solvent), greener choices can be made in its handling and transformations.

• Greener solvent swaps (general; literature)

  • Replace DCM with EtOAc or toluene where feasible (workups, extractions, and many coupling reactions can tolerate EtOAc).
  • Use 2-MeTHF or CPME instead of THF for reductions and enolate chemistry; both are less volatile and often derived from renewable feedstocks.
  • Favor MeOH/EtOH over IPA/MeCN when compatible with reaction selectivity.

• Greener reagents and conditions (general)

  • Chemoselective ketone reduction: NaBH4 in green alcohol solvents often suffices, avoiding pyrophoric hydrides.
  • Ester saponification under aqueous conditions minimizes organic solvent use; consider continuous-flow or microwave assistance to reduce energy/time.
  • Amidation: use water-compatible coupling systems (e.g., EDCI/HOAt alternatives or enzyme-catalyzed couplings) to reduce hazardous reagents.

• Waste and energy reduction

  • Employ solvent recovery (EtOAc, toluene, 2-MeTHF recycle well).
  • Prefer catalytic hydrogenation over stoichiometric metal hydrides when chemoselectivity allows (using EtOH or EtOAc as solvent).

Comparison snapshot (general)

• THF → 2-MeTHF: similar polarity; higher hydrophobicity aids phase separation; better stability toward peroxide formation than ethers like diethyl ether.
• DCM → EtOAc: eliminates chlorinated solvent; often similar solubility for hydrophobic substrates; slightly higher bp can extend reaction times but improves safety.

Pharmaceutical Uses

No excipient or pharmacopeial status is provided for this item.

• Item-specific information

  • Intended use: For research use only (per Product Data).
  • Pharmacopeia/monograph status: Not specified for this item; refer to CoA/Spec Sheet.

• General context (non-clinical)

  • In drug discovery and process chemistry, aryl keto esters like this are employed as synthetic intermediates to access carboxylic acids, amides, alcohols, and amines. They can be leveraged to modulate lipophilicity and aromatic substitution patterns in lead series.
  • Any use in pharmaceutical manufacturing would be as an intermediate subjected to further transformation and purification; it is not intended for direct inclusion in formulations.

Physical Properties

Item-specific physicochemical specifications (bp, mp, density, refractive index, UV cutoff, residuals) are not provided in the Product Data for this SKU.

• Item-specific values

  • Boiling point: Not specified for this item; refer to CoA/Spec Sheet.
  • 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: Not specified for this item; refer to CoA/Spec Sheet.
  • LogP / pKa: Not specified for this item; refer to CoA/Spec Sheet.

• Literature-based expectations (for planning only; not product specifications)

  • Physical state: typically an oil or low-melting solid for long-chain aryl–alkyl keto esters (literature).
  • Polarity: moderately hydrophobic due to aryl and aliphatic chain; ester and ketone confer limited polarity (literature).
  • Solubility profile: usually soluble in common organic solvents (EtOAc, DCM, THF, toluene, MeOH) and poorly soluble in water (literature).

Always verify exact values on the item’s CoA/Spec Sheet prior to process design.

Quality and Grades

• Item-specific quality information

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

• How to interpret common grades (general guidance)

  • Research grade: suitable for synthetic and analytical work; limits for trace impurities are fit for most R&D uses.
  • Analytical/HPLC grade (if applicable): minimized nonvolatile residue and UV background for chromatography.
  • Synthetic intermediate grade: typically controls on residual solvents, assay by NMR/GC/LC, and identity (NMR/HRMS/IR).

• Verification and documentation

  • For each lot, consult the CoA for assay method (qNMR, LC purity), residual solvent data, and identity confirmation (e.g., 1H/13C NMR).
  • Stabilizers: none are listed for this item in the Product Data. If present in a specific lot, the CoA will disclose them; implications include downstream purification or compatibility with catalysts.

• Practical note for this chemotype

  • Aryl–alkyl keto esters can display minor enol content; purity assays should account for potential tautomeric signals.
  • If you require low-UV-absorbing material for detection near 254–280 nm, specify UV cutoffs and LC purity upfront (not specified here).

Reaction and Applications

As a bifunctional 1,7-dicarbonyl equivalent, Ethyl 8-(2,3-dichlorophenyl)-8-oxooctanoate is a versatile intermediate for assembling aryl–aliphatic frameworks and for late-stage diversification.

• Transformations at the ketone (general literature)

  • Chemoselective reduction to the secondary alcohol using NaBH4 or catalytic hydrogenation, typically leaving the ester intact.
  • Oxime/hydrazone formation for derivatization or protection; conditions: hydroxylamine or hydrazine derivatives in EtOH/AcOH.
  • Reductive amination to install benzylic secondary/tertiary amines (NaBH3CN, NaBH(OAc)3; solvents like DCE/MeOH). The ester usually remains untouched.

• Transformations at the ester (general literature)

  • Saponification to the corresponding acid, enabling amide coupling (HATU, EDCI, DIC) or further diversification.
  • Alcoholysis/transesterification (acidic or basic) to adjust protecting group strategy.
  • Reduction to primary alcohols (LiAlH4) or aldehydes (DIBAL-H, carefully controlled at low temperature).

• Chain and ring constructions (general)

  • Enolate chemistry at positions alpha to the ester enables alkylation or Michael additions; the distal aryl ketone provides additional chemoselectivity handles.
  • Intramolecular cyclizations (e.g., intramolecular aldol) to form medium rings may be explored, leveraging the 1,7-distance between carbonyls.

• Use cases in discovery chemistry (general)

  • Installation of lipophilic aryl tails with orthogonal reactivity for SAR studies.
  • Precursor to ω-aryl carboxylic acids/amides bearing a benzylic alcohol or amine after selective ketone modification.

Reaction Conditions

The following are general, literature-style conditions commonly used for this chemotype. They are not item-specific specifications.

• Chemoselective ketone reduction (leaving ester intact)

  • NaBH4 (1.5–3.0 eq), MeOH or EtOH, 0–25 °C, 0.5–3 h; typical isolated yields 70–95% for secondary alcohols.
  • Catalytic hydrogenation (H2, 1–5 bar) with Pd/C in EtOH or EtOAc at rt–40 °C can reduce the ketone; monitor for potential dehalogenation on the 2,3-dichlorophenyl ring.

• Reductive amination at the ketone

  • Carbonyl + amine (1.2–2.0 eq) with NaBH3CN or NaBH(OAc)3 in DCE/MeOH or THF/AcOH, 0–25 °C, 2–16 h; yields commonly 60–90%.

• Ester hydrolysis (saponification)

  • NaOH or KOH (1.1–2.0 eq) in MeOH/H2O or THF/H2O, 0–25 °C to reflux, 1–6 h; acidify to isolate the carboxylic acid; typical yields 80–95%.

• Ester reduction

  • DIBAL-H (1.1–1.5 eq) in toluene or CH2Cl2 at −78 to −20 °C for partial reduction to aldehyde; quench cautiously. LiAlH4 (2–3 eq) in THF at 0–25 °C for full reduction to primary alcohol.

• Enolate alkylation (at the ester alpha-position)

  • LDA (1.1–1.5 eq) in THF or 2-MeTHF at −78 to −20 °C, then alkyl halide; quench at low temperature, warm to rt; variable yields 40–80% depending on electrophile.

Caution: The 2,3-dichloroaryl ring can be sensitive to strong nucleophiles and catalytic hydrogenation (risk of dechlorination). Optimize conditions and monitor closely by LC/MS or NMR.

Safety and Handling

• Regulatory/GHS (item-specific)

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

• General hazards for aryl keto esters (literature guidance; not a substitute for SDS)

  • May cause skin/eye irritation and respiratory irritation if mist/vapor is generated.
  • Combustible organic; keep away from ignition sources.

• PPE and lab practices

  • Wear appropriate PPE: lab coat, safety goggles, and nitrile gloves.
  • Handle in a fume hood to avoid inhalation of vapors/aerosols.
  • Avoid strong bases and strong acids that can promote ester hydrolysis or transesterification; avoid strong oxidizers.

• First-aid overview (follow institutional procedures; consult SDS)

  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Skin contact: wash with soap and water; remove contaminated clothing.
  • Eye contact: rinse cautiously with water for several minutes; seek medical advice if irritation persists.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.

• Storage incompatibilities and stability

  • Store tightly closed at room temperature (per Product Data) in a dry place.
  • Protect from moisture and prolonged UV exposure; esters can slowly hydrolyze under basic or acidic conditions.

Always consult the product-specific SDS for authoritative safety information.

Solvent Selection

This compound is a moderately hydrophobic aryl–aliphatic keto ester. Solvent choice depends on the transformation (ketone vs ester chemistry) and on solubility constraints.

• General polarity/miscibility (literature)

  • Expected to dissolve well in medium-polarity organic solvents (DCM, EtOAc, THF, MeCN) and in aromatic hydrocarbons (toluene). Poor water solubility is expected.

• Typical solvent choices by operation (general)

  • Reductions of the aryl ketone (chemoselective): MeOH, EtOH, i-PrOH, or THF with NaBH4; alcohols accelerate hydride delivery to ketones.
  • Saponification of the ester: MeOH/H2O or THF/H2O with NaOH or KOH.
  • Amide coupling after hydrolysis: DMF, DCM, or MeCN with carbodiimide/uronium reagents.
  • Electrophilic aromatic substitutions on the ring are disfavored by dichloro deactivation; if attempted, use polarizable solvents (HFIP/TFA mixtures) with caution.

• Comparison with alternatives (general)

  • EtOAc vs DCM: EtOAc offers greener profile and comparable solubility; DCM may give faster phase separations and higher solubility for hydrophobic substrates.
  • 2-MeTHF or CPME vs THF: greener ethers with higher hydrophobicity can improve solubility and facilitate extractions.

Confirm solubility empirically for your lot; no item-specific solubility data are provided here.

Storage and Reconstitution

• Storage (item-specific)

  • Storage conditions: Room temperature (per Product Data). Store in a tightly closed container in a dry, well-ventilated area.
  • Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

• Stability and handling (general guidance)

  • Protect from moisture and prolonged exposure to strong acids/bases to minimize ester hydrolysis and side reactions.
  • If long-term storage is planned, consider protecting from light and storing under inert gas to limit oxidative degradation of sensitive functionalities.

• Reconstitution

  • Supplied neat; no reconstitution is typically required. If a solution is needed, prepare immediately before use in an appropriate dry solvent (e.g., EtOAc, THF, DCM, toluene) and store solutions at low temperature when feasible.

• Freeze–thaw guidance

  • Not applicable for neat solids/oils. For prepared solutions, avoid repeated freeze–thaw; aliquot as needed.

For definitive shelf-life and solution stability, consult the lot-specific CoA/Spec Sheet.

Structure and Identity

Ethyl 8-(2,3-dichlorophenyl)-8-oxooctanoate is an aryl–aliphatic 1,7-dicarbonyl building block bearing an ethyl ester at one terminus and an aryl alkyl ketone at the other.

• Item-specific IDs (from Product Data)

  • SKU: E947631
  • CAS: 898777-93-0
  • PubChem CID: 24727526
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed identifiers and features (general reference)

  • Typical molecular formula: C16H20Cl2O3 (literature)
  • Typical molecular weight: ~331.24 g/mol (literature)
  • Structural features: one ethyl ester (–C(=O)OCH2CH3), one aryl–alkyl ketone (–CO–Ar), a flexible hexamethylene spacer between the carbonyls, and a 2,3-dichlorophenyl ring.
  • Functional groups: secondary aryl ketone, aliphatic ethyl ester; multiple enolizable methylenes adjacent to each carbonyl.

• 2D structure description (general)

  • Linear chain: EtO–C(=O)–(CH2)6–C(=O)–ArCl2, where ArCl2 is a phenyl ring substituted by Cl at the 2- and 3-positions relative to the acyl attachment.
  • No stereogenic centers are present; the molecule is achiral.

Notes: Literature/computed fields are provided for context only and are not item-specific specifications.

Synthetic Utility

Key functional handles enable orthogonal and chemoselective transformations:

• Orthogonal reactivity

  • Aryl ketone: readily undergoes nucleophilic addition (hydride, organometallics), imine/oxime formation, and reductive amination. It is more reactive than the ester toward hydride sources like NaBH4, enabling selective reductions.
  • Ethyl ester: stable to many nucleophiles and weak bases; can be hydrolyzed to the acid, reduced (LiAlH4, DIBAL-H), or converted to amides via coupling.

• Enolate chemistry (general)

  • The methylenes alpha to the ester can be deprotonated with LDA, NaHMDS, or weaker bases under phase-transfer to enable C–C bond formation (alkylation, Michael additions). The distant aryl ketone provides an additional carbonyl for potential intramolecular strategies.

• Retrosynthetic value

  • Disconnection at the aryl ketone suggests access via Friedel–Crafts acylation of 2,3-dichlorobenzene derivatives with an appropriate acid chloride, followed by esterification, or via coupling of a 2,3-dichloroacyl chloride with a protected ω-ester.
  • The ester end serves as a versatile linchpin for late-stage diversification to acids, amides, or alcohols without perturbing the aryl ketone-derived stereoelectronics.

• Protection strategies

  • The ketone may be masked as an acetal/ketal if conditions risk reduction or condensation, while the ester protects the acid functionality during multi-step sequences.

Target Specificity

Not applicable. This product is a small-molecule synthetic intermediate and is not an antibody, enzyme, or ligand with defined biological target specificity.

• Item-specific target/epitope/clone/isotype data: Not specified for this item.

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 898777-93-0, the molecular formula is C16H20Cl2O3, and the molecular weight is 331.23 g/mol. InChIKey GANNSLPPFDIBRT-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.