Ethyl 8-chloro-2-oxooctanoate , CAS No.717919-91-0

CAS: 717919-91-0 Cat. No.: E964693 Formula: C₁₀H₁₇ClO₃ Peso molecolare: 220.69 PubChem CID: 24722235

Storage

Room temperature

Specifications

Condizioni di conservazione di stoccaggio

Room temperature

Nomi e identificatori

Sorrisi canonici

CCOC(=O)C(=O)CCCCCCCl

IUPAC Name

ethyl 8-chloro-2-oxooctanoate

InChIKey

OQRSLBNWMVQWPP-UHFFFAOYSA-N

INCHI

1S/C10H17ClO3/c1-2-14-10(13)9(12)7-5-3-4-6-8-11/h2-8H2,1H3

Isomeri SMILES

CCOC(=O)C(=O)CCCCCCCl

PubChem CID

24722235

Peso molecolare

220.69

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Classe Fatty Acyls
      • Subclass Fatty acid esters

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Classe: Fatty Acyls
• Subclass: Fatty acid esters
• Intermediate Tree Nodes: Not available
• Direct Parent: Fatty acid esters
• Alternative Parents: Alpha-keto acids and derivatives Ketones Carboxylic acid esters Monocarboxylic acids and derivatives Organochlorides Organic oxides Hydrocarbon derivatives Alkyl chlorides
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Fatty acid ester - Alpha-keto acid - Keto acid - Carboxylic acid ester - Ketone - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Alkyl chloride - Organohalogen compound - Organochloride - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Carbonyl group - Organic oxygen compound - Alkyl halide - Aliphatic acyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
• 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: 220.690 g/mol
• XLogP3: 2.500
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 9
• Exact Mass: 220.087 Da
• Monoisotopic Mass: 220.087 Da
• Topological Polar Surface Area: 43.400 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 180.000
• 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 validated bioassay or immunoassay protocols are associated with this small-molecule reagent in the product data. Application is reaction‑dependent; see the Reaction & Applications and Reaction Conditions sections for general synthetic guidance.

For analytical control in synthetic use, typical protocols include:

• Identity/purity checks by 1H/13C NMR, IR (carbonyl bands for keto and ester), and LC‑MS/GC‑MS.
• Monitoring reactions by TLC with UV visualization (α‑dicarbonyls often show strong UV) and carbonyl‑specific stains (e.g., 2,4‑DNPH for keto functionality).

Biological Roles

No biological function is specified for this catalog item; it is supplied for research use only.

General context (literature):

• α‑Keto acids (2‑oxo acids) are central intermediates in metabolism (e.g., pyruvate, 2‑oxoglutarate), undergoing transamination, decarboxylation, and redox transformations. While Ethyl 8‑chloro‑2‑oxooctanoate is a synthetic derivative rather than a known natural metabolite, its α‑keto motif can participate in analogous chemical transformations in vitro.
• ω‑Chloroalkyl chains can serve as electrophilic handles to tether the molecule to nucleophilic biomolecules in chemical biology experiments (e.g., forming alkylated adducts with thiols or amines under controlled conditions). Any such use should be confined to in‑vitro research settings with appropriate controls and safety practices.

No claims are made regarding biological activity, selectivity, or in vivo relevance. Researchers should design assays that account for the general electrophilicity of α‑keto carbonyls and alkyl chlorides and control for non‑specific modification of biomolecules.

Buffer Applications

This compound is a non-ionic organic α‑keto ester and is not used as a buffering agent. It lacks acid–base pairs appropriate for maintaining pH in aqueous systems.

• Guidance: For work involving this reagent, select an external buffer system compatible with your reaction or assay (e.g., phosphate, HEPES, or acetate) and verify that it does not promote ester hydrolysis or undesired nucleophilic substitution at the ω‑chloro site.
• If conducting biphasic chemistry or extractions, choose buffers near neutral pH to minimize saponification of the ester.

Green Alternatives

Greener choices often relate to solvent and process rather than changing the substrate itself.

• Solvent alternatives (comparative, literature)

  • Replace CH2Cl2 with EtOAc or 2‑MeTHF when feasible (comparable polarity, easier recovery; 2‑MeTHF is bio-derived and supports low‑temperature enolization chemistry).
  • Substitute DMF/DMSO in SN2 with MeCN or propylene carbonate when kinetics allow; MeCN is more volatile and easier to remove, while propylene carbonate is low‑toxicity/low‑vapor‑pressure.
  • Use CPME or cyclohexane/EtOAc blends for extraction/chromatography to reduce halogenated solvent waste.

• Reagent/process choices

  • For reductive amination, employ hydrogenation (H2 with Pd/C or Raney Ni) instead of hydride donors where compatible—lower waste and easier purification (literature).
  • Employ aqueous micellar catalysis for some SN2 substitutions on ω‑chloro groups using surfactants (e.g., TPGS‑750‑M), minimizing organic solvent use (emerging literature).

• Trade‑offs

  • 2‑MeTHF/CPME can retain peroxides; implement routine peroxide testing and inhibitor management.
  • MeCN has toxicity concerns and requires proper capture; propylene carbonate may slow reactions due to higher viscosity.
  • Hydrogenation requires pressure equipment and careful safety controls; hydride reagents generate salt waste but are operationally simple.

Pharmaceutical Uses

No pharmacopeial status or excipient role is specified for this item; it is supplied strictly for research and laboratory use.

General notes (non-clinical, formulation chemistry context):

• α‑Keto esters can serve as synthetic intermediates toward prodrugs or lipophilic modifiers in medicinal chemistry workflows, but this listing makes no claims regarding suitability for clinical development.
• Any use in preclinical formulation would require independent evaluation of purity, stability (to hydrolysis and enolization), and extractables/leachables; none of these specifications are provided here and must be established by the user.

Physical Properties

No item-specific physical constants were supplied for this catalog entry. The following notes distinguish between unspecified values and general expectations.

• Item-specific values (specs)

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Melting/Boiling Point: Not specified for this item; refer to CoA/Spec Sheet.
  • Density, Refractive Index: Not specified for this item; refer to CoA/Spec Sheet.
  • Solubility in water/organics: Not specified for this item; refer to CoA/Spec Sheet.

• General chemistry expectations (literature, for α‑keto ethyl esters of medium chains)

  • Physical state: typically colorless to pale liquids for C8‑chain esters (literature), with low water solubility and good solubility in common organic solvents (Et2O, CH2Cl2, EtOAc, THF, hexanes/tert‑butyl methyl ether).
  • Volatility: moderate; distillation often feasible under reduced pressure (literature).
  • Acidity/basicity: α‑keto position on the aliphatic side is enolizable; ester carbonyl is non‑basic (literature).

Note: Use item CoA/SDS for authoritative constants when planning purifications or scaling. Where a specific numeric value is critical (e.g., refractive index for identity checks), consult the lot-specific documentation.

Quality and Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• UV cutoff, residual water, metal content, stabilizer: Not specified for this item; refer to CoA/Spec Sheet.

Guidance for this compound class (general):

• Research-use material: supplied for R&D only; not for human or veterinary use. For reactions sensitive to trace acid/base, verify acidity/alkalinity by micro-titration or small-scale testing.
• α‑Keto esters may be prone to slow self-condensation under basic conditions; high-purity material should be handled under neutral/dry conditions. If specifications include inhibitors or stabilizers, understand their impact on your transformation (e.g., traces of acid inhibiting base-catalyzed steps).
• If HPLC or GC identity is required, request CoA for retention data and any spectroscopic fingerprints (1H/13C NMR, IR, MS) available for the supplied lot.
• For chromatography-heavy workflows, a low-UV-absorbing solvent system and pre-dried silica can reduce tailing of polar carbonyl compounds (general best practice).

Reaction and Applications

This reagent integrates an α‑keto ester core with an ω‑chloro handle, enabling divergent synthesis.

• Transformations at the α‑keto ester
  • Reductive amination (literature): converts the α‑keto into α‑amino esters under catalytic hydrogenation (e.g., H2/Pd, or NaBH3CN in presence of amines and mild acid). Useful for accessing amino‑functionalized fatty ester analogs.
  • Nucleophilic additions: organometallics (RMgX/RLi) add to the α‑keto, furnishing tertiary/secondary alcohols after workup; control over-addition to the ester requires low temperature and protective strategies.
  • Enolization/α‑functionalization: deprotonation α to the keto (on the aliphatic side) enables halogenation, acylation, or aldol-type couplings. Use non-nucleophilic bases (LDA/LiHMDS) in dry ether solvents.
• Transformations at the ω‑chloro terminus
  • SN2 substitution with O-, N-, S‑nucleophiles (alkoxides, amines, thiolates) to introduce diverse polar headgroups; phase-transfer conditions can be effective.
  • Azidation (NaN3) followed by Staudinger or CuAAC elaboration to triazoles (literature pathway to click handles).
  • Elimination to terminal alkene under strong base (E2), enabling subsequent hydroboration/oxidation or epoxidation sequences.
• Tandem/orthogonal strategies
  • Sequential ω‑substitution then α‑keto elaboration allows convergent construction of bifunctional molecules (e.g., lipidic probes, linkers).
  • Intramolecular cyclizations are possible after introducing a nucleophile at the terminus (e.g., tethered amine/thiol) to form medium rings via SN2 or lactamization, with the ester/keto providing additional activation handles.
• Practical notes
  • Maintain anhydrous conditions to avoid ester hydrolysis and self-condensation under base.
  • For ω‑SN2, choose bases that do not deprotonate/enolize the α‑keto site unless desired; carbonate or tertiary amines are often gentler alternatives.

Reaction Conditions

The following are general literature-style guidelines for common transformations of α‑keto esters and ω‑chloroalkyl groups. These are not item-specific specifications.

• Reductive amination at the α‑keto
  • Typical: amine (1.2–2.0 equiv), AcOH (0.1–0.5 equiv) in MeOH or EtOH, then NaBH3CN (1.2–1.5 equiv) at 0–25 °C, 2–16 h. Alternatively, H2 (1–5 bar) with Pd/C (5–10 wt%) in alcohol at RT–50 °C.
• Organometallic addition to the α‑keto
  • RMgX or RLi (1.1–1.5 equiv) in THF/Et2O at −78 to 0 °C, 0.5–2 h; quench with saturated NH4Cl. Protect the ester if over‑addition is a concern.
• α‑Functionalization via enolization (adjacent to the keto on the aliphatic side)
  • LDA or LiHMDS (1.1–1.5 equiv) in THF at −78 to −40 °C, followed by electrophile (e.g., Br2, ClCO2R, RCHO). Strictly anhydrous.
• ω‑SN2 substitutions
  • Nucleophile (1.5–3.0 equiv) with base (K2CO3, Cs2CO3, or NaH for alcohols/thiols) in DMF/MeCN at 25–80 °C, 2–24 h; monitor for competing E2 at higher temperatures/with strong base.
• ω‑Azidation and click
  • NaN3 (2–3 equiv) in DMF at 60–80 °C, 4–16 h; CuAAC thereafter with alkyne in t‑BuOH/H2O (1:1) using CuSO4/sodium ascorbate at RT.

Yields vary widely (literature), depending on substrate and conditions. Always perform small‑scale optimization and monitor by TLC/GC/HPLC/LC‑MS.

Safety and Handling

Hazard classification specifics were not provided for this product entry; consult the SDS for authoritative information.

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

Practical handling guidance (general for α‑keto esters and ω‑chloroalkyl esters; defer to SDS):

• Likely hazards: irritant to skin/eyes; harmful if swallowed or inhaled. ω‑Chloroalkyl groups and α‑keto functionality may cause mucous membrane irritation (literature, general chemical knowledge).
• PPE: wear lab coat, safety glasses or splash goggles, and appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood to minimize inhalation exposure.
• Storage incompatibilities: avoid strong bases (can induce undesired condensations/eliminations), strong nucleophiles (SN2 at –CH2Cl), and strong oxidants/reductants. Keep away from moisture and prolonged light/heat.
• Spill/first aid overview: in case of skin/eye contact, rinse with copious water for ≥15 minutes; remove contaminated clothing. If inhaled, move to fresh air. If ingested, do not induce vomiting; seek medical attention. Follow institutional protocols.
• Reactivity notes: α‑keto esters can form enamines/enols; control base exposure. ω‑Chloro groups undergo SN2 with strong nucleophiles; segregate from amines/thiolates unless intended.
• Waste: collect halogenated organic waste separately per local regulations.

Solvent Selection

Solvent choice should reflect the dual reactivity: an α‑keto ester motif and an ω‑chloroalkyl handle.

• Polarity/miscibility (general expectations)
  • Likely miscible with: CH2Cl2, CHCl3, THF, EtOAc, MTBE/CPME, toluene, hexanes mixtures (literature, general for medium-chain ethyl esters).
  • Sparingly soluble in water (literature); use biphasic systems (e.g., toluene/aqueous base) judiciously to limit hydrolysis.
• Selection by operation
  • Nucleophilic substitution at –CH2Cl: polar aprotic solvents (DMF, DMSO, MeCN) promote SN2; ensure anhydrous conditions to avoid ester hydrolysis.
  • Reductive amination or additions to the α‑keto: alcohols (MeOH, EtOH) or MeCN/THF often used with hydrogenation or borohydride variants; buffer pH where relevant in two-phase systems.
  • Carbon–carbon bond formations (aldol-type at the α‑position to the keto): THF or toluene with strong non-nucleophilic bases (LDA, LiHMDS); rigorously dry, low-temperature.
• Comparison notes
  • CH2Cl2 vs toluene: CH2Cl2 often improves solubility and rate for polar transitions; toluene is preferred when minimizing chlorinated solvent use or at higher temperatures.
  • THF vs DMF: THF is easier to remove and compatible with organometallics; DMF offers higher polarity for SN2 but can engage in side reactions at high base loadings.

Storage and Reconstitution

• Storage conditions (from Product Data): Room temperature.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Container: Use amber glass with PTFE‑lined cap when possible to minimize light exposure and headspace moisture ingress (general best practice for esters and α‑keto compounds).
• Stability notes (general):
  • Keep tightly closed under dry, inert atmosphere for extended storage to minimize hydrolysis and adventitious base exposure.
  • Avoid prolonged contact with strong bases or nucleophiles; the ω‑chloro group is susceptible to substitution, and the ester can hydrolyze.
  • If distillation is required, use reduced pressure and minimal hold times at elevated temperatures.
• Reconstitution: Not applicable; supplied neat (no reconstitution instructions provided). If preparing stock solutions, use dry, oxygen‑free solvents (e.g., anhydrous CH2Cl2, THF, or MeCN), store at 2–8 °C or RT depending on solvent, and use within a few days.
• Research Use Note: For research use only.

Structure and Identity

Ethyl 8-chloro-2-oxooctanoate is an α-keto ester bearing a terminal (ω) chloro substituent on an eight‑carbon backbone, offering two distinct functional handles: a reactive α‑keto carbonyl adjacent to the ester and an ω‑chloroalkyl site for substitution.

• Item-specific identifiers (from Product Data)
  • SKU: E964693
  • Product Name: Ethyl 8-chloro-2-oxooctanoate
  • CAS: 717919-91-0
  • InChIKey: 264897 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Composition descriptors
  • 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 chemistry description)
  • Functional groups: ethyl ester (–COOEt), α‑keto (2‑oxo, R–CO–COOR′), terminal ω‑chloro (–CH2Cl).
  • Connectivity (2D description in words): an ethyl ester of 2‑oxooctanoic acid with chlorination at C8 (the terminal carbon). From the ester carbonyl (C1), the adjacent carbon (C2) is a ketone carbonyl; the aliphatic chain continues to C8, which is substituted with chlorine (–CH2Cl).
  • Stereochemistry: none specified; the name does not imply any stereogenic centers.
• Synonymy/context (literature): Often described as an α‑keto (2‑oxo) long‑chain ethyl ester bearing an ω‑chloro handle (literature).

Synthetic Utility

Ethyl 8‑chloro‑2‑oxooctanoate is a bifunctional synthon enabling orthogonal elaborations on both ends of the molecule.

• α‑Keto ester handle
  • Reductive amination → α‑amino esters (precursors to amino‑functional lipids or surfactants).
  • Organometallic additions to the α‑keto → tertiary alcohols; protecting strategies may be required to prevent over‑addition to the ester.
  • α‑Functionalization via enol/enolate chemistry on the aliphatic side (halogenation, acylation, aldol couplings).
  • Decarboxylative pathways after hydrolysis (via α‑keto acids) can generate ketones under oxidative or thermal conditions (literature).
• ω‑Chloro terminus
  • SN2 substitution to introduce azides, amines, thiols, or alkoxides, enabling late‑stage diversification or installation of reporter groups (fluorophores/biotin via linkers).
  • E2 elimination to terminal alkenes for further olefin chemistry (hydroboration–oxidation, cross‑metathesis).
• Convergent assembly
  • Acts as a linchpin for constructing amphiphiles: polar headgroup via ω‑substitution and core modifications via α‑keto chemistry.
  • Can be incorporated into solid‑phase or solution‑phase diversification libraries owing to its complementary reactive sites.

Operational considerations: keep conditions anhydrous and avoid prolonged exposure to strong base unless exploiting enolate chemistry; control temperature to manage chemoselectivity between the keto and ester carbonyls.

Target Specificity

Not applicable. This product is a small-molecule reagent and not an affinity reagent or biological targeting agent. No antigen/epitope, species reactivity, clone, or isotype information applies.

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 717919-91-0, the molecular formula is C10H17ClO3, and the molecular weight is 220.69 g/mol. InChIKey OQRSLBNWMVQWPP-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.