This compound belongs to the class of organic compounds known as phenylmorpholines. These are aromatic compounds containing a morpholine ring and a benzene ring linked to each other through a CC or a CN bond.
External Descriptors
morpholines - delta-lactam
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
233.310 g/mol
XLogP3
2.500
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
2
Exact Mass
233.142 Da
Monoisotopic Mass
233.142 Da
Topological Polar Surface Area
29.500 Ų
Heavy Atom Count
17
Formal Charge
0
Complexity
279.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
1
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
1
Calcolatori di soluzioni
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Recensioni
Recensioni dei clienti
Application Protocols
No tested biological or analytical application protocols are provided for this item.
General suggestions (informational; verify experimentally):
Stock solution preparation: weigh accurately and dissolve in dry DMSO to 10–50 mM; sonicate gently if needed. Filter through 0.22 µm PTFE for particulate removal before biological assays.
Reaction set-up: dry glassware, inert atmosphere (N2/Ar) for moisture-sensitive steps; use anhydrous solvents and monitor by TLC/LC-MS.
Purification: flash chromatography on silica with EtOAc/hexanes or DCM/MeOH gradients; adjust based on polarity. For final polishing, consider preparative HPLC if UV-visible response is adequate.
For any specific downstream application, develop and document a fit-for-purpose protocol as this listing includes no validated procedures.
Biological Roles
Item-specific biological data
None provided for this SKU. No biochemical target or pathway data are specified.
General context (informational; research-only, no medical claims)
Morpholinone-containing scaffolds appear in discovery programs as polarity-tuning motifs: the lactam contributes a strong hydrogen bond acceptor and reduces basicity relative to morpholine, often aiding passive permeability/clearance balance.
The ortho-disubstituted aryl group (2-ethyl-6-methylphenyl) introduces steric bulk and a lipophilic vector that can project into hydrophobic binding pockets in screening campaigns.
Typical in vitro studies for such scaffolds include ADME profiling (solubility, permeability, microsomal stability) and broad target screening to establish tractable SAR; none of these data are provided here for this specific compound.
This product is supplied strictly for laboratory research use. Any biological evaluation should be conducted under appropriate approvals and in accordance with institutional guidelines.
Buffer Applications
This compound is a neutral organic building block and is not typically used to formulate laboratory buffer systems.
No buffer system, pH range, or composition is applicable for this item.
For solution preparation aimed at biological assays, dissolution is generally performed in organic co-solvents (e.g., DMSO) before dilution into assay media, as solubility in water is typically limited for aryl lactams. Validate solubility and assay compatibility empirically.
Refer to sections Solvent Selection and Storage & Reconstitution for practical guidance on preparing stock solutions.
Green Alternatives
Because this product is a solid organic building block rather than a process solvent, greener practice focuses on solvent and reagent choices when using it.
Prefer greener solvents when feasible (informational):
Replace dichloromethane with ethyl acetate or methyl tert-butyl ether (MTBE) for extractions and chromatography, when separation allows.
Substitute DMF/NMP with dimethyl carbonate, propylene carbonate, or Cyrene for coupling/alkylation if reactivity and stability are compatible.
Use 2-MeTHF or CPME instead of THF for moisture-tolerant reactions; both offer improved safety and lifecycle metrics.
Reagent choices:
Opt for organic bases (e.g., DBU, BTMG) or carbonate bases over strong inorganic bases where compatible to reduce hazard and waste.
Employ catalytic methods (e.g., Pd-catalyzed cross-coupling with ppm-level catalysts, photoredox) to minimize stoichiometric metals.
Work-up/waste minimization:
Design crystallization-driven isolations to avoid large solvent volumes.
Implement aqueous phase neutralization and brine minimization strategies; recover and recycle EtOAc/MeCN where permissible.
Comparison snapshot (general)
THF vs 2-MeTHF: similar polarity; 2-MeTHF derived from renewables, higher bp, better phase separation; may change reaction kinetics.
DCM vs EtOAc: EtOAc less toxic and biodegradable; may reduce extraction efficiency for very polar species.
Evaluate on small scale to balance greenness with yield, selectivity, and impurity control.
Pharmaceutical Uses
No pharmacopeial status or excipient role is specified for this item; it is provided for research use only.
General R&D context (informational)
Potential role: a discovery chemistry intermediate or screening compound. Morpholinone motifs can modulate physicochemical properties in lead optimization, but this listing includes no data on formulation or clinical use.
Pre-formulation considerations for research samples:
Stock solutions are commonly prepared in DMSO or DMF and stored at low millimolar to high millimolar concentrations, then diluted into assay buffers immediately before use.
Salt formation is less straightforward for lactams (weakly basic); if higher aqueous solubility is needed, consider prodrug approaches or formulate with solubilizers (e.g., cyclodextrins) in exploratory studies.
Manufacturing/CMC: not applicable; no GMP grade or compendial monograph is provided.
All uses must remain within non-clinical, laboratory research contexts.
Physical Properties
Item-specific facts (from Product Data)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Other specifications (bp, mp, density, refractive index, solubility): Not specified for this item; refer to CoA/Spec Sheet.
Literature/general expectations for aryl‑substituted morpholin-3-ones (informational, not item specifications)
Physical state: typically crystalline solids or low-melting solids due to rigid lactam ring and aryl substituent.
Polarity: moderate polarity from the lactam; often soluble in moderately polar organic solvents (e.g., DCM, EtOAc, THF) and in polar aprotic media (DMF, DMSO). Limited aqueous solubility is common unless ionized.
Acid–base: the lactam nitrogen is weakly basic; protonation can increase aqueous solubility in strong acid. No pKa values are provided for this specific item.
Thermal behavior: lactams generally have defined melting points and good thermal stability below decomposition; aryl ortho-substitution can increase melting point via packing, but steric clash can also lower it—empirical data are required.
Please consult the item’s CoA/Spec Sheet for exact, tested physical properties applicable to this specific SKU.
Quality and Grades
Item-specific quality information (from Product Data)
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on grades (general information)
Research grade: commonly supplied for discovery chemistry; purity is typically established by HPLC/GC and NMR. If a specific assay (e.g., ≥98% by HPLC) is important for your work, confirm the current lot’s CoA.
Trace metal / residual solvent limits: not specified for this item. For catalytic or analytical sensitivity, request extended analytics (metals by ICP-MS, residual solvents by GC) if needed.
Stabilizers/inhibitors: none are indicated for this item. If your application is moisture- or acid-sensitive, consider storing with a desiccant and under inert atmosphere even when not explicitly required.
Documentation: each shipped lot is accompanied by or linked to a CoA detailing analytical methods and results. For method suitability (e.g., LC-UV vs. LC-MS), request chromatograms to ensure compatibility with your detection wavelength and matrix.
Note: In the absence of a specified grade on this page, treat this product as research-use only material. Verify exact purity, water content, and other QC attributes in the lot-specific CoA/Spec Sheet.
Reaction and Applications
Item-specific applications (from Product Data)
Manufacturer applications: Not specified for this item.
Research Use Note: For research use only.
General applications for 4-aryl-5-methylmorpholin-3-ones (informational)
Medicinal chemistry scaffold: morpholinone cores are frequently used to modulate polarity, H-bonding, and metabolic stability in lead series. The 2-ethyl-6-methylphenyl group introduces ortho congestion, influencing conformational bias and potentially selectivity in target binding screens.
Building block behavior: the lactam nitrogen can undergo N-alkylation or N-acylation under basic conditions, expanding SAR rapidly. The 5-methyl substituent can sometimes be functionalized via benzylic-type oxidation or halogenation if enolizable (assess experimentally).
Derivatization options:
Electrophilic activation of the lactam carbonyl for ring-opening to furnish β-amino acid/amide derivatives.
Directed metalation on the aryl ring is disfavored by ortho substituents; instead, prefunctionalization (e.g., halogenation via SEAr on activated positions) may be explored if electronics permit.
Reductive transformations of the lactam (e.g., partial reduction to hemiaminal-type species) under carefully chosen hydride conditions.
Platform for library synthesis: late-stage diversification at nitrogen, and potential C–H functionalization on the aryl ring using modern catalytic methods (e.g., Ir-catalyzed borylation at least hindered positions, then cross-coupling).
All transformations require orthogonal protection/activation strategies validated on small scale before scale-up.
Reaction Conditions
No item-specific, validated reaction conditions are provided for this SKU. The following are general literature-style guidelines for related transformations; they are not specifications.
N-Alkylation of lactams: base such as NaH or K2CO3 in DMF/MeCN, 0–25 °C to initiate, then 25–60 °C as needed. Monitor by LC-MS; typical times 1–12 h. Avoid overalkylation by using slight excess of electrophile and controlled addition.
N-Acylation: acid chloride/anhydride with Et3N or DIPEA in DCM/THF, 0–25 °C; catalytic DMAP can accelerate. Quench cautiously and wash with bicarbonate to remove acids.
Benzylic-type functionalization at C-5 methyl (if feasible): NBS/AIBN in CCl4 or safer alternatives (NBS in MeCN with light) at 0–25 °C; radical conditions require thorough safety assessment. Follow with nucleophile trapping.
Lactam reduction: BH3·THF (under inert atmosphere) 0 °C to reflux; or catalytic hydrogenation with suitable catalysts under mild conditions. Workup borane complexes carefully.
Aryl diversification (if prefunctionalized): Suzuki coupling using Pd(dppf)Cl2·DCM (1–2 mol%), K3PO4 (2–3 equiv), dioxane/water (4:1), 80–100 °C, 4–16 h. Optimize ligand/base per substrate.
Always dry solvents and exclude moisture/air where base- or metal-catalyzed methods are used. Confirm stability of this specific compound under chosen conditions prior to scale-up.
Safety and Handling
Item-specific hazard information (from Product Data)
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 (informational; defer to SDS for authoritative guidance)
Personal protective equipment: wear lab coat, safety glasses or face shield, and appropriate chemically resistant gloves (e.g., nitrile). Handle in a fume hood to avoid inhalation of dusts or vapors generated during processing.
Avoid: contact with strong oxidizers and strong acids/bases that may lead to degradation or ring-opening; avoid heating above decomposition temperatures. Prevent dust formation; use local exhaust during weighing and charging.
First aid overview: in case of skin contact, wash with soap and water; for eye contact, rinse cautiously with water for several minutes; if inhaled, move to fresh air; if ingested, rinse mouth. Seek medical attention as needed. Always follow the SDS instructions.
Spill/cleanup: contain solid spills by gentle sweeping while minimizing dust; absorb solutions with inert material. Dispose of waste according to institutional and regulatory requirements.
Fire safety: organic heterocycles are typically combustible. Use CO2, dry chemical, or foam as appropriate. Combustion can produce CO/CO2 and nitrogen oxides.
Always consult the Aladdin Scientific SDS for this catalog item prior to use.
Solvent Selection
Item-specific facts (from Product Data)
No measured solubility profile is provided for this SKU. Refer to CoA/Spec Sheet for any available solubility notes.
General guidance for aryl morpholin-3-ones (informational)
Polarity class: moderately polar neutral heterocycle (lactam). Often dissolves in polar aprotic and moderately polar organic solvents.
Typical solvents for dissolution or reaction media:
Conditional: methanol/ethanol (check for limited solubility; risk of transesterification is negligible for lactams but monitor for alcoholysis under strong acid/base).
Poor: nonpolar alkanes (e.g., hexanes) unless co-solvent is used.
Miscibility notes: choose high-dielectric solvents (DMSO/DMF/MeCN) for kinetic transformations or when using polar reagents; DCM/EtOAc are practical for workup and chromatography.
Selection tips:
For N-acylation/alkylation: use dry, polar aprotic solvents (DMF/MeCN) with non-nucleophilic bases.
For cross-couplings on the aryl ring (if a leaving group is introduced): dioxane/DMF/toluene mixtures are commonplace.
For crystallization: EtOAc/hexanes or MeOH/water mixtures may be screened.
These are literature-style guidelines; confirm solvent compatibility and solubility empirically for your batch.
Storage and Reconstitution
Item-specific storage (from Product Data)
Storage conditions: Room temperature.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
General handling and reconstitution (informational)
Container: store tightly closed in the original amber vial to minimize moisture and light exposure. Adding a small desiccant pack in secondary containment is advisable for heterocycles.
Inert atmosphere: not required by specification, but purging headspace with nitrogen/argon can improve long-term integrity for sensitive applications.
Stock solutions: prepare concentrated stocks in anhydrous DMSO, DMF, or acetonitrile. Typical research stocks: 10–50 mM in DMSO. Record exact solvent and concentration on the vial.
Stability of solutions: many lactam-containing compounds are stable for weeks at 2–8 °C in dry organic solvents; however, confirm by LC before critical use. Avoid repeated freeze–thaw by aliquoting.
Aqueous use: if dilution into aqueous buffers is required, add organic stock slowly with vigorous mixing to avoid precipitation; keep final DMSO ≤1–2% v/v for cell-based assays when applicable.
Always consult the lot-specific CoA and SDS for definitive storage and handling instructions.
InChIKey: 73610 (as provided; note this string is atypical in length for an InChIKey)
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 description (literature/general)
Core scaffold: a morpholin-3-one (a 6-membered heterocycle containing N and O with a lactam carbonyl at the 3-position).
Substitution pattern: aryl substitution at the 4-position with a 2-ethyl-6-methylphenyl group; an additional methyl at the 5-position of the morpholinone ring.
Functional groups: cyclic amide (lactam), ether (ring oxygen), tertiary-like amide nitrogen in a constrained ring; substituted alkyl-aryl (o-ethyl, o-methyl) creating steric hindrance around the biaryl junction.
Stereochemistry: no stereocenters are implied by the name; the ring is achiral in the absence of additional stereogenic elements.
2D depiction in words: a six-membered O–C(=O)–C–C–N ring (morpholin-3-one) bearing a methyl at C-5 and an aryl at C-4; the aryl is a benzene ring carrying an ethyl at ortho-1 relative to the attachment point and a methyl at ortho-3 relative to the attachment point.
Synthetic Utility
A 4-aryl-5-methylmorpholin-3-one is a versatile heterocyclic platform for derivatization and library expansion.
Functional handles:
Lactam nitrogen: suitable for N-alkylation (SN2 with alkyl halides under basic conditions) or N-acylation (acid chlorides/anhydrides with base). Protecting strategies (e.g., Boc on nitrogen) may be applied if orthogonality is needed.
C-5 methyl: potential for oxidative or radical functionalization to introduce diversity (e.g., NBS under radical conditions for benzylic-type bromination; verify selectivity).
Aryl ring: heavily ortho-substituted (2-ethyl, 6-methyl) limits directed ortho-metalation; late-stage diversification more likely via C–H borylation at less hindered positions followed by Suzuki couplings, subject to feasibility.
Transformations:
Ring opening of the activated lactam to β-amino derivatives provides access to linear scaffolds.
Reduction: selective partial reduction conditions (e.g., borane for lactams) can afford corresponding morpholinols or aminals; control conditions to avoid overreduction.
Cross-coupling: if a halide/boronate is installed on the aryl ring, standard Pd-catalyzed Suzuki/Negishi protocols can be employed to append substituents.
Retrosynthetic value: serves as a masked β-amino carbonyl equivalent, enabling convergent coupling routes where the lactam ring is unveiled or transformed late stage to modulate liabilities.
These strategies are general to the class; confirm reactivity with small-scale trials and appropriate analytical monitoring.
Target Specificity
No target, antigen, enzyme, receptor, or pathway specificity is provided for this product.
This SKU is offered as a research chemical building block. It is not an antibody, protein, or assay-validated ligand in this catalog entry.
If you require target-annotated screening compounds, contact Aladdin Scientific with the desired target class to check availability of appropriately characterized materials.
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