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.
Stock solutions: Prepare at 10–100 mM in dry DMSO, DMF, or acetonitrile for high-throughput synthesis or assay seeding; filter (0.2 μm PTFE) if particulates are present.
Gradient: 5%→95% B over 5–10 min; ESI+ detection leveraging tertiary amine protonation.
Purification: Silica gel chromatography using EtOAc/hexanes or DCM/MeOH (0–5% MeOH with 0.1% Et3N to suppress tailing of the basic morpholine).
For any bioassay or materials application, develop method-specific protocols and validate for your system.
Biological Roles
This product is supplied for research and synthetic chemistry; no biological function is claimed for the material itself.
General considerations (literature/guidance for related motifs):
Morpholine-containing aromatics often serve as polarity-tuning elements in small molecules due to the tertiary amine and ether oxygen, enabling salt formation and improving aqueous compatibility in probe or lead-like compounds.
β-Keto esters are pro-nucleophilic units that can be transformed into diverse heterocycles and carbonyl compounds frequently encountered in bioactive libraries; however, the parent β-keto ester typically lacks specific biological roles.
Protonation state: At physiological pH, morpholine nitrogens (pKaH ~8–9 in simple morpholine, literature) may be partially protonated, affecting membrane permeability and binding profiles when embedded within larger molecules.
No cellular targets, pathways, or biochemical activities are assigned to this catalog item. Any biological evaluation should be performed within the context of newly synthesized derivatives or conjugates using appropriate controls.
Research Use Note: For research use only.
Buffer Applications
Not typically applicable. This compound is an organic synthetic building block rather than a buffering agent. It does not constitute a recognized buffer system.
Practical guidance:
If dissolution in aqueous systems is required for assays, consider forming a water-soluble salt (e.g., HCl salt) of the morpholine nitrogen or using co-solvents (DMSO, MeOH) followed by dilution into buffered media.
Select buffer components (e.g., phosphate, acetate, HEPES) based on the biology/assay requirements; avoid strong basic or strongly acidic conditions that may hydrolyze the β-keto ester.
Green Alternatives
Selecting greener solvents and processes can reduce environmental footprint while preserving performance in β-keto ester chemistry.
Greener solvent swap ideas (literature/guidance):
Replace chlorinated solvents where possible:
DCM/chloroform → EtOAc, 2-MeTHF, or CPME for extractions and medium-polarity reactions.
Replace petroleum ethers/hexanes in crystallizations:
Use heptane or cyclopentyl methyl ether (CPME) with EtOAc to reduce VOC toxicity.
For enolate chemistry:
2-MeTHF often substitutes for THF in LDA-based alkylations (better safety profile, higher boiling point, partially bio-based). Ensure similar enolate solubility and consider temperature adjustments due to different cryoscopic behavior.
For polar media needs:
Minimize DMF/DMSO usage by employing acetonitrile, propylene carbonate, or green amide solvents (e.g., NBP, Cyrene) where compatible with base and nucleophiles.
Small comparison (general):
2-MeTHF vs THF: bio-based, forms fewer peroxides, higher bp (80 vs 66 °C, literature), but can have water content variability; enolate reactions may require drier conditions.
EtOAc vs DCM: similar medium polarity and extraction performance; EtOAc is biodegradable with lower halogenated waste, but can be more prone to hydrolysis under strong base.
Process tips:
Employ telescoped sequences to avoid isolating sensitive intermediates.
Use solvent recycling and in-line drying (molecular sieves) to limit waste.
Favor catalytic over stoichiometric reagents when feasible (organocatalysis for Knoevenagel/Michael additions).
Pharmaceutical Uses
No pharmacopeial or excipient status is specified for this item; it is provided strictly for research use.
Context (general, non-clinical):
Role as an intermediate: Aryl β-keto esters with tertiary amines are common intermediates in medicinal chemistry campaigns for tuning lipophilicity, basicity, and hydrogen-bonding capacity. They enable rapid analog generation via enolate chemistry and N-functionalization of the morpholine.
Salt formation: The tertiary amine facilitates salt screening (e.g., HCl, mesylate, fumarate) to modulate solid-state properties of downstream targets. Such operations apply to derivatives, not to the catalog item as a drug substance.
Formulation development (screening stage): For in vitro tool compounds, stock solutions are often prepared in DMSO and diluted into aqueous vehicles; ensure compatibility with assay buffers to prevent ester hydrolysis.
No therapeutic indications, dosing, or clinical claims are made or implied for this product.
Physical Properties
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight (MW): Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Boiling point / Melting point: Not specified for this item; refer to CoA/Spec Sheet.
Density, refractive index, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
Solubility (general expectations; literature/guidance, not item-specific):
Likely soluble in common organic solvents such as dichloromethane, chloroform, ethyl acetate, THF, acetone, and acetonitrile due to the ester/ketone functions and aryl ring.
The morpholine tertiary amine may enhance solubility in alcohols (MeOH, EtOH) and partially in water when protonated (e.g., in dilute acid), but the overall hydrophobic scaffold typically limits aqueous solubility at neutral pH.
Acid–base behavior (literature/guidance): The morpholine nitrogen is a weak base (pKb ~5.6 in simple morpholine; pKaH ~8–9, literature). The β-keto ester methylene is enolizable (typical pKa ~10–13 for analogous systems), enabling enolate formation under basic conditions.
Partitioning (qualitative, literature/guidance): Expected amphiphilic character: lipophilic aryl/alkyl domain with a polar tertiary amine ether; anticipate moderate logP in neutral form and increased hydrophilicity upon protonation.
For authoritative, item-specific physical constants, consult the product CoA/Spec Sheet.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
When grade is provided (e.g., ≥95%, ≥98%):
Assay indicates the chromatographic purity of the principal component; trace residual solvents or inorganics may be present unless otherwise noted.
For structure-rich building blocks like this β-keto ester bearing a morpholine substituent, minor impurities can include regioisomers, over-alkylation products, or hydrolysis byproducts; the CoA chromatogram can help assess suitability for sensitive applications.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet. β-Keto esters typically do not require added inhibitors; they benefit from dry storage to minimize hydrolysis.
Identity confirmation: Expect NMR (1H/13C), HRMS/ESI, and HPLC/GC purity on the CoA. The presence of both carbonyls (ester and ketone), aromatic signals, and morpholine methylenes are diagnostic in NMR.
Use-case guidance:
For synthesis development or SAR libraries, ≥95% purity is often adequate.
For methodology benchmarking or when trace amines/esters interfere (e.g., catalysis screens), consider higher-purity material or repurification in-house (silica gel, recrystallization).
Regulatory note: This catalog item is supplied for research use only; it is not subjected to pharmacopeial monographs unless explicitly stated on the CoA.
Reaction and Applications
As an aryl-substituted β-keto ester bearing a tertiary amine (morpholine), this building block is well-suited to enolate chemistry, cyclizations, and late-stage diversification.
Enolate generation and C–C bond formation:
Strong bases (e.g., LDA, LiHMDS, NaH) deprotonate the methylene between the ketone and ester to afford a stabilized enolate. This enables alkylation, Michael additions, and aldol condensations with electrophiles such as alkyl halides, acrylates, and aldehydes (literature precedents for β-keto ester chemistry).
Decarboxylative strategies: Thermal or base-promoted Krapcho-like conditions can transform β-keto esters, while selective saponification/decarboxylation sequences allow access to ketones after hydrolysis of the ester (literature guidance for acetoacetate analogs).
Heterocycle construction: Intramolecular condensations with appended electrophiles furnish carbocycles or heterocycles; the morpholinomethyl-phenyl unit can guide proximity effects or serve as a directing/basic site.
Amine functionalization: The morpholine nitrogen can be quaternized, acylated, or sulfonylated to tune physicochemical properties (e.g., to generate salts or ionic tags for purification/analytical purposes).
Cross-coupling adjunct: While the aryl ring here is not halogenated, installing a halide or boronate on the aryl unit (in a prior step) allows Suzuki, Buchwald–Hartwig, or Heck elaborations while retaining the β-keto ester handle for orthogonal diversification.
Library synthesis: Orthogonal handles (enolizable carbonyl and tertiary amine) support parallel synthesis for medicinal chemistry scaffolds and fragment elaboration.
Always control moisture and temperature to avoid ester hydrolysis; buffer basic workups to protect the β-keto ester functionality.
Reaction Conditions
General conditions for β-keto ester transformations (literature guidance; not item-specific):
Enolate alkylation:
Base: LDA (1.1–1.5 equiv) in THF or 2-MeTHF, −78 to −20 °C; add alkyl halide (1.2–2.0 equiv); warm to 0–25 °C over 1–4 h. Typical isolated yields for simple systems: 60–85% depending on electrophile and sterics.
Alternatives: NaH (60% in oil) in THF/DMF at 0–25 °C; LiHMDS in THF/toluene at −78 to 0 °C.
Michael addition:
Base: DBU, K2CO3, or t-BuOK; solvent: MeCN, THF, or toluene; 0–60 °C, 2–16 h. Catalytic secondary amines (enamine catalysis) can be used for asymmetric variants.
Knoevenagel condensation:
Catalyst: ammonium acetate, piperidine, or basic alumina; solvent: toluene, ethanol, or acetonitrile; 25–110 °C, water removal (Dean–Stark) improves conversions.
Hydrolysis/decarboxylation:
Saponification with NaOH/MeOH–H2O (0–25 °C), then acidify and heat (80–120 °C) for decarboxylation to the corresponding ketone (two-step sequence typical for acetoacetate analogs).
Amine derivatization:
N-acylation with acyl chlorides (Et3N or DIPEA, DCM, 0–25 °C). N-alkylation with alkyl halides (K2CO3, MeCN/acetone, 25–60 °C). Quaternization in MeCN or acetone often proceeds at rt–50 °C.
Analytical monitoring: LC-MS in ACN/H2O (0.1% FA) with ESI+; β-keto ester enol/keto tautomerism can yield dual peaks in NMR; dry solvents minimize exchange.
Note: The morpholine nitrogen may coordinate bases/acids; adjust equivalents to avoid competitive N-alkylation when C-alkylation is desired.
Safety and Handling
GHS classification / Signal word / H-statements / Pictograms: Not specified for this item; refer to the SDS for definitive hazard information.
General hazards (class-based guidance): Aromatic β-keto esters and tertiary amine-containing compounds are commonly classified as irritants to skin, eyes, and respiratory tract. Avoid inhalation of dust/aerosols and contact with skin or eyes. Morpholine derivatives may be harmful if swallowed.
PPE: Lab coat, appropriate gloves (e.g., nitrile), safety glasses or face shield; handle in a fume hood to minimize exposure to vapors/aerosols.
Handling notes:
Avoid strong acids and bases that can lead to hydrolysis (ester cleavage) or uncontrolled enolization/condensation.
Prevent prolonged exposure to elevated temperatures that could promote decomposition or transesterification.
Keep containers tightly closed to limit moisture uptake and oxidation.
Incompatibilities (general): Strong oxidizers; strong acids/bases; reactive acylation/alkylation agents that may modify the morpholine nitrogen; sodium hydride or other strong bases require controlled addition and anhydrous conditions if enolization is intended.
First aid (overview; consult SDS):
Skin/eye contact: Rinse with plenty of water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
Inhalation: Move to fresh air; seek medical attention if symptoms occur.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Fire safety: Use CO2, dry chemical, or foam. Combustible organic; thermal decomposition may produce COx and nitrogen-containing fumes. Refer to SDS for detailed firefighting measures.
Waste: Dispose via licensed chemical waste contractor in accordance with local regulations.
Solvent Selection
This compound is a polar, multifunctional organic molecule (β-keto ester + tertiary amine ether). Solvent choice should balance enolate chemistry needs with amine basicity and overall polarity.
Polarity class (guidance): Moderately polar, aprotic preference for enolate reactions; protic alcohols or mildly acidic media can protonate the morpholine and increase solubility when needed.
Likely miscibility/solubility (general): Good solubility expected in DCM, chloroform, EtOAc, acetone, acetonitrile, THF, DMF/DMSO; limited in hexanes/heptane unless co-solvent is used.
When to choose which solvent:
Enolate formation/alkylation: Anhydrous THF, MTBE, toluene, or DME with strong bases (LDA, NaH). Polar aprotics (DMF/DMSO) can enhance rates but complicate workup.
Catalytic hydrogenation or transfer hydrogenation of aryl substituents (if applicable): EtOH/EtOAc mixtures or MeOH with buffered conditions to avoid ester cleavage.
Salt formation/purification: Use alcohol/ether mixtures with a volatile acid (HCl in dioxane/Et2O) to crystallize the hydrochloride salt of the morpholine, enhancing handling and storage.
Crystallization: Ethyl acetate/hexanes or toluene/EtOAc screens are typical for aryl β-keto esters; protonation state will influence solid form.
Analytical solvents: ACN/H2O with 0.1% formic acid for LC-MS (positive ESI expected). For NMR, CDCl3 or DMSO-d6; CD3OD may exchange enolic protons and broaden signals.
Alternatives: For greener choices, consider 2-MeTHF or CPME in place of THF/DCM; see Green Alternatives tab for tradeoffs.
Storage and Reconstitution
Storage conditions (item-specific): Room temperature (as provided). Store in a tightly closed container, protected from moisture and direct light.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Stability considerations (general): β-Keto esters can undergo slow hydrolysis or transesterification in the presence of moisture or base. Keep the material dry; use desiccant and minimize headspace if long-term storage is anticipated.
Reconstitution/dissolution (guidance):
For synthetic use, dissolve in dry organic solvents such as DCM, THF, EtOAc, acetone, acetonitrile, DMF, or DMSO. Sonication and gentle warming (≤40 °C) may aid dissolution.
For aqueous work, consider forming a protonated salt (e.g., HCl salt) of the morpholine nitrogen to enhance water compatibility, or use a co-solvent approach (DMSO → buffer dilution).
Freeze–thaw: If solutions are prepared for storage, aliquot to avoid repeated freeze–thaw. Store solutions at −20 to 4 °C depending on solvent; protect from moisture and air.
Research Use Note: For research use only.
Refer to the product CoA/Spec Sheet and SDS for definitive handling and stability data.
Structure and Identity
Ethyl 6-[2-(morpholinomethyl)phenyl]-6-oxohexanoate is an aryl-substituted β-keto ester incorporating a tertiary amino ether (morpholine) side chain.
InChIKey (as provided): 41799 (note: provided identifier appears truncated; consult CoA/SDS for full string)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
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 description):
Core scaffold: A hexanoate chain bearing a β-keto ester motif (–CO–CH2–CO2Et) at C-6 (6-oxohexanoate), esterified as an ethyl ester.
Aryl substituent: The chain is substituted at the terminal (C-6) carbonyl-bearing carbon with a 2-(morpholinomethyl)phenyl group, i.e., an ortho-benzylmorpholine attached via a methylene linker to the aromatic ring.
Functional groups: One aromatic ring, one tertiary amine within a morpholine ring (O- and N-heterocycle), one ketone (β to the ester), and one ethyl ester.
Stereochemistry: As named, no stereocenters are specified; the molecule is expected to be achiral in its free form (literature expectation for this substitution pattern).
2D structure in words: Ethyl acetoacetate-like fragment extended to a hexanoate, whose carbonyl-bearing quaternary center is bonded to an ortho-benzylmorpholine-substituted phenyl ring; morpholine confers basicity and polar character, while the aryl β-keto ester confers enolizability.
Synthetic Utility
Key functional elements and how to exploit them:
β-Keto ester manifold:
Readily forms enolates/enamines, enabling C-alkylation, Michael addition, and aldol-type condensations. Suitable for Knoevenagel condensations with aldehydes to access α,β-unsaturated esters.
Selective hydrolysis/decarboxylation leads to substituted ketones (classic acetoacetate transformations), expanding access to aryl-alkyl ketone motifs.
Morpholine tertiary amine:
Amenable to N-acylation, N-alkylation, N-oxide formation, or quaternization, allowing polarity and binding modulation. Quaternary ammonium derivatives aid in phase-switch purification.
Aryl handle:
Electrophilic aromatic substitution (if suitably activated) or, after prior installation of a halide/boronate on a precursor, cross-coupling routes to diversify the aryl domain while retaining the β-keto ester.
Orthogonal reactivity: The basic nitrogen and enolizable carbonyl provide two independent vectors for diversification, facilitating parallel synthesis and SAR exploration.
Cyclizations: Intramolecular condensation with tethered electrophiles can yield tetralone, chromanone, or indane-like frameworks depending on substitution patterns (general strategy for aryl β-keto esters).
Practical tips:
Strictly anhydrous conditions for strong-base steps; quench carefully to minimize transesterification.
Consider temporary amine protection (e.g., Boc) if competing N-alkylation is problematic during C-alkylation sequences.
Monitor by LC-MS (ESI+) where the tertiary amine enhances ionization efficiency.
Target Specificity
Not applicable. This product is a small-molecule building block and is not an antibody, protein, or biochemical reagent with defined biological targets.
No antigen/epitope, clone, isotype, or species reactivity information applies.
For target engagement studies, derivatives synthesized from this scaffold would need to be evaluated empirically.
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