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
296.790 g/mol
XLogP3
4.200
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
10
Exact Mass
296.118 Da
Monoisotopic Mass
296.118 Da
Topological Polar Surface Area
43.400 Ų
Heavy Atom Count
20
Formal Charge
0
Complexity
304.000
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 validated bioassay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule building block. For synthetic usage, refer to Reaction Conditions and Application notes provided in other sections.
Biological Roles
This product is a synthetic organic building block without an inherent biological role. No endogenous metabolic, signaling, or structural function is associated with ethyl 8-(2-chlorophenyl)-8-oxooctanoate.
Literature/general context:
Aryl–aliphatic keto-esters can serve as precursors to amides, alcohols, and acids used in probe development or materials chemistry; any biological studies would involve derivatives rather than the parent compound.
The ortho-chloro substituent provides a potential handle for cross-coupling to introduce bioactive motifs; however, the parent compound itself is not a ligand, cofactor, or metabolite.
Research use only: Not for human or veterinary use.
Buffer Applications
Not typically applicable. Ethyl 8-(2-chlorophenyl)-8-oxooctanoate is a hydrophobic organic building block rather than a buffering agent. It does not participate in defined acid–base equilibria suitable for laboratory buffering in the physiological pH range. For practical use, focus on sections covering Reaction & Applications, Synthetic Utility, and Solvent Selection.
Green Alternatives
While the compound itself is a target building block, greener choices pertain primarily to reaction and workup media (literature/general guidance):
Replace chlorinated solvents where feasible:
DCM/CHCl3 → EtOAc, MTBE, CPME, or toluene for extractions and chromatography.
Swap petroleum ethers/hexane with heptane or cyclopentyl methyl ether (CPME) to reduce VOC hazard and improve recyclability.
Use bio-derived ethers: 2-MeTHF (from hemicellulose) as a greener alternative to THF for organometallic additions and reductions; often affords improved phase separation and lower peroxide propensity.
Alcohol/water systems for reductions or hydrolyses when compatible (e.g., NaBH4 in ethanol; aqueous base for saponification) to minimize halogenated waste.
Catalysis and atom economy:
Employ catalytic hydrogenation (H2/Pd) for ketone reductions where selectivity permits, rather than stoichiometric hydrides.
Use enzymatic ester hydrolysis or amidation (lipases, acyl transferases) for mild, aqueous-compatible routes when functional group tolerance allows.
Small comparison (general):
THF vs 2-MeTHF: Similar reactivity for Grignard and LDA chemistry; 2-MeTHF offers higher boiling point, easier separations, and renewable sourcing, but may solvate some bases less effectively at very low temperatures.
DCM vs EtOAc: EtOAc is biodegradable and less toxic; DCM provides superior silica mobility and solubility for very nonpolar mixtures. Choose EtOAc when separation allows.
Note: Validate solvent changes by pilot experiments; monitor for altered selectivity or rates.
Pharmaceutical Uses
No pharmacopeial monograph or excipient designation is provided for this item. The compound is best regarded as a synthetic intermediate/building block.
Intermediate en route to amides, alcohols, or acids bearing a 2-chlorobenzoyl motif.
Diversification via aryl chloride cross-coupling to access libraries of analogs for SAR exploration during early discovery.
Compliance note: This product is for research use only and is not intended for use in humans or for manufacturing of active pharmaceutical ingredients without further qualification. No therapeutic claims are made or implied.
Physical Properties
Item-specific specs are not provided; values below are literature/computational guidance only for planning.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Boiling point: Not specified for this item; refer to CoA/Spec Sheet. (Large, nonvolatile keto-ester; typically distilled only under high vacuum if at all.)
Melting point: Not specified for this item; refer to CoA/Spec Sheet.
Density: Not specified for this item; refer to CoA/Spec Sheet. (Literature expectation: ~1.1–1.2 g/mL for chlorinated aryl keto-esters, but confirm experimentally.)
Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
LogP: Expected high (literature: lipophilic due to aryl ring and C8 chain; cLogP likely >3). Exact value not specified.
pKa: No titratable groups in the neutral range; carbonyl alpha C–H acidity typical of ketones/esters (literature: pKa ~20–25 for ketone α-CH, ~25–26 for ester α-CH in DMSO), but no item-specific value.
Solubility (literature/general):
Soluble in common organic solvents (DCM, CHCl3, EtOAc, THF, toluene, acetonitrile).
Low solubility in water due to hydrophobic aryl and long alkyl chain.
Vapor pressure: Expected very low (literature/general for C16 aryl esters). Not specified for this item; refer to CoA/Spec Sheet.
Note: Use these literature descriptors for method development only; for specifications relevant to QC/release, consult the CoA/Spec Sheet.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Inhibitors: None indicated. Not specified for this item; refer to CoA/Spec Sheet.
Guidance for interpretation (general):
For synthetic building blocks like aryl keto-esters, key quality attributes typically include identity (1H/13C NMR), purity by HPLC/GC, water content (Karl Fischer), and residual solvents. If relevant to your application (e.g., photochemistry, bioconjugation), review UV cutoff/trace metals, but these are Not specified for this item; refer to CoA/Spec Sheet.
If an assay grade (e.g., 95%, 98%+) is required for a sensitive step (e.g., asymmetric catalysis), request the latest CoA and batch-specific impurity profile.
UV absorbance: Aromatic systems may exhibit significant absorbance <300 nm; if using for analytical calibration or photochemical steps, assess baseline in your solvent system (not specified as an item spec).
Recommendation: For moisture/acid/base-sensitive transformations, pre-dry the material under vacuum and verify purity by LC or NMR prior to use.
Reaction and Applications
Ethyl 8-(2-chlorophenyl)-8-oxooctanoate is a versatile bifunctional building block combining an aryl ketone and an alkyl ethyl ester separated by a C6 spacer. Literature/general synthetic uses include:
Chemoselective carbonyl transformations:
NaBH4 or catalytic transfer hydrogenation can reduce the aryl ketone preferentially, leaving the ester intact, affording secondary alcohols that retain the ester (useful for subsequent intramolecular cyclizations or ester elaboration).
LiAlH4 or DIBAL-H (at low temperature) enables stepwise reduction: ketone to alcohol and/or ester to primary alcohol; conditions dictate selectivity.
Enolate chemistry at the ketone α-position: The methylene adjacent to the aryl ketone can be deprotonated (LDA, NaHMDS) for alkylation, aldol additions, or Michael additions, installing further functionality remote from the ester.
Ester functionalization:
Saponification to the corresponding acid (then amidation via EDC/HOBt, HATU, or CDI) provides amide-linked analogs.
Transesterification to introduce alternative alcohol handles (e.g., benzyl, tert-butyl) for protecting-group strategies.
Cross-coupling diversification on the aryl chloride after prior functional interconversions: The ortho-chloro substituent on the phenyl ring can be transformed via Pd-catalyzed Suzuki, Buchwald–Hartwig amination (after oxidative addition), or Negishi couplings—typically facilitated if the ketone is protected as an acetal or converted downstream to mitigate catalyst poisoning.
Intramolecular cyclizations: After ketone reduction to a secondary alcohol, activation (e.g., tosylation) can enable cyclization to medium rings; alternatively, Dieckmann-type strategies on derivatives of the ester can form rings incorporating part of the tether.
Applications: Synthesis of aryl-alkyl scaffolds, linker-modified benzoyl derivatives, and as a handle to construct 1,ω-difunctional intermediates for materials or probe synthesis.
Reaction Conditions
General literature guidance (optimize for your system; not item-specific specifications):
Selective ketone reduction:
NaBH4 (1–2 equiv) in MeOH or MeOH/DCM at 0–25 °C, 0.5–2 h. Typically reduces the ketone faster than the ester. Quench with NH4Cl. Monitor by TLC/LC.
Catalytic hydrogenation (H2, 1–3 bar) with Pd/C (5–10 wt%) in EtOH or EtOAc at rt–40 °C can reduce the ketone; check for potential dechlorination under forcing conditions.
Ester hydrolysis (saponification):
NaOH (1–2 M) in MeOH/H2O (4:1 to 1:1), 20–50 °C, 1–6 h to give the acid. Acidify to pH ~2 and extract with EtOAc.
DIBAL-H reduction to aldehyde:
DIBAL-H (1.1–1.5 equiv) in toluene or 2-MeTHF at −78 to −40 °C, 0.5–2 h. Quench with Rochelle salt. Avoid over-reduction of the ketone by temperature control/protecting groups.
Organometallic addition to the ketone:
RMgX (1.2–2.0 equiv) in THF or 2-MeTHF at −20 to 0 °C, 0.5–3 h affords tertiary alcohols after aqueous quench. Protect ester if necessary to prevent transesterification.
Enolate formation/alkylation at ketone α-position:
LDA (1.1–1.5 equiv) in THF or THF/HMPA alternative (e.g., DMPU) at −78 to −40 °C, then add primary electrophile (RX). Typical times 0.5–2 h.
Cross-coupling at aryl chloride (on derivatives where needed):
Suzuki–Miyaura: Pd2(dba)3 (1–2 mol%), XPhos/SPhos (2–4 mol%), base (K3PO4), 2-MeTHF/toluene/H2O, 60–100 °C, 2–16 h. Consider carbonyl protection.
Yields: Highly substrate- and condition-dependent; consult primary literature and perform small-scale optimization before scale-up.
Safety and Handling
GHS classification, pictograms, and H-statements are not provided for this catalog entry. Always consult the SDS for authoritative safety information.
GHS classification: Not specified for this item; refer to SDS.
Signal word/H-statements/Pictograms: Not specified for this item; refer to SDS.
General laboratory handling (good practice, literature-based for aryl keto-esters):
PPE: Use lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Work in a fume hood to avoid inhalation of vapors or aerosols.
Incompatibilities: Avoid strong bases and strong acids in the presence of water (ester hydrolysis/transesterification). Strong nucleophiles (hydrides, organometallics) will react with the ketone and/or ester carbonyls. Oxidants may affect the aryl ring under forcing conditions.
Special risks: Not an ether—no specific peroxide hazard expected. Combustible organic liquid/solid; keep away from ignition sources.
First aid (overview; defer to SDS):
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; obtain medical advice.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Spills: Absorb with inert material (vermiculite, sand), collect for disposal. Prevent entry into drains.
Waste: Dispose of as organic chemical waste per institutional and local regulations.
Storage conditions (from Product Data): Store at room temperature.
Solvent Selection
This product is a hydrophobic aryl–aliphatic keto-ester intended as a reagent/building block (not a bulk solvent). The following selection guidance (literature/general) supports its use in synthesis and purification:
Polarity/miscibility (expected):
Soluble in moderately polar aprotic and nonpolar organic solvents: DCM, CHCl3, EtOAc, THF, toluene, MeCN.
Poorly soluble in water; aqueous workups will partition into organic layers (increase EtOAc/MTBE proportion for efficient extraction).
Typical selections by operation:
Nucleophilic additions to the ketone: THF, 2-MeTHF, or diethyl ether for Grignard/organolithium; toluene/CPME for hydride reductions.
Selective ketone reduction over ester: MeOH/EtOH or i-PrOH with NaBH4 (monitor chemoselectivity), or DCM/MeOH mixtures.
Ester hydrolysis or amidation: MeOH/THF/H2O (basic saponification), or DMF/DCM with coupling reagents for aminolysis.
Friedel–Crafts acylation analog development or further acyl manipulations: non-nucleophilic solvents (DCM, nitrobenzene, chlorobenzene) with Lewis acids when applicable to derived substrates.
Purification: Flash chromatography with hexanes/EtOAc or toluene/EtOAc gradients typically provides good resolution from aromatic by-products.
Comparison notes (general):
THF vs 2-MeTHF: 2-MeTHF often offers improved phase separation and greener profile; both solvate organometallics well.
DCM vs EtOAc: DCM provides high solubility and fast chromatography; EtOAc is greener and safer but may give broader bands.
Storage and Reconstitution
Storage conditions (Product Data): Store at room temperature.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Form/appearance: Not specified for this item; refer to CoA/Spec Sheet.
General guidance (literature/practice for keto-esters):
Protect from moisture and strong acids/bases to minimize ester hydrolysis or transesterification during storage.
If long-term storage is anticipated, keep in a tightly sealed amber container under inert gas (N2/Ar) to limit oxidation and adventitious moisture uptake.
Reconstitution/preparation:
For stock solutions, dissolve in anhydrous organic solvents (e.g., DCM, THF, 2-MeTHF, EtOAc, toluene, MeCN) at convenient concentrations (0.1–1.0 M). Filter if necessary through PTFE.
For air/moisture-sensitive downstream steps, make solutions in a glovebox or using drybox techniques; pre-dry solvent over molecular sieves (3Å/4Å).
Freeze–thaw: Not typically required for this class. If storing solutions, aliquot to avoid repeated warming and minimize hydrolysis.
Stability: The aryl ketone is generally stable; the ethyl ester can slowly hydrolyze under humid/alkaline/acidic conditions. Verify integrity by NMR/LC before critical uses.
Always consult the latest CoA/SDS for batch-specific handling and stability details.
Structure and Identity
Ethyl 8-(2-chlorophenyl)-8-oxooctanoate is an aryl–aliphatic keto-ester building block featuring a terminal benzoyl unit (2-chlorobenzoyl) tethered to an ethyl octanoate via a saturated C6 spacer.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: C16H21ClO3 (computed from name/literature)
Molecular weight: ~296.79 g/mol (computed)
Structural features (descriptive, literature-based):
Functional groups: one aryl ketone (2-chlorobenzoyl) and one ethyl ester.
Ring systems: monosubstituted 2-chlorophenyl ring bonded to the ketone carbonyl carbon.
Connectivity (2D description): EtO2C–(CH2)6–C(=O)–C6H4–Cl(ortho). The carboxyl-derived carbonyl is on one end (ethyl ester), while the opposite end bears a benzoyl carbonyl directly attached to an ortho-chloro phenyl ring.
Stereochemistry: none (acyclic, no stereogenic centers in the named structure).
Category path: 全部 / 可售 / 生命科学
Research use: For research use only.
Synthetic Utility
Key functional groups and reactivity (literature/general):
Aryl ketone site:
Electrophilic toward nucleophiles (RMgX, RLi, hydrides) to furnish tertiary/secondary alcohols after workup.
Enolizable α-CH enables formation of kinetic (LDA, −78 °C) or thermodynamic (NaHMDS, −20 to 0 °C) enolates for C–C bond formation (alkylation, aldol, Michael additions).
Protecting options: Convert to ketal/acetal to enable aryl chloride cross-couplings without carbonyl interference.
Ethyl ester terminus:
Hydrolysis (NaOH, MeOH/H2O) to the carboxylic acid; subsequent coupling (EDC/HOBt, HATU) to amides/peptides.
Reduction (DIBAL-H, −78 to −20 °C) to the corresponding aldehyde; LiAlH4 to primary alcohol.
Transesterification (acidic or basic catalysis) to tailor protecting groups or install handles (e.g., benzyl for later hydrogenolysis).
Aryl chloride handle (ortho to the carbonyl):
Pd-catalyzed cross-couplings (Suzuki, Negishi, Stille, Buchwald–Hartwig amination) to introduce heteroaryl/alkyl/amine functionality, enabling diverse late-stage diversification.
Strategic value:
Serves as a linear 1,ω-difunctional synthon with orthogonal reactivity (ketone vs ester vs aryl–Cl), useful in modular assembly of linkers, macrocycle precursors, and conjugation-ready scaffolds.
Facilitates convergent routes: functionalize each end independently, then close rings or append pharmacophores as needed.
Target Specificity
Not applicable. This product is a small-molecule building block and is not an antibody, oligonucleotide, or biological probe with defined target specificity. No antigen/epitope, clone, isotype, or species reactivity information applies.
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