This compound belongs to the class of organic compounds known as morpholine carboxylic acids and derivatives. These are heterocyclic compounds containing a morpholine ring substituted by one or more carboxylic acid groups (or derivative thereof).
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.
Zertifikate (CoA, COO, BSE/TSE und Analyse-Diagramm)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemische und physikalische Eigenschaften
Molekulargewicht
261.100 g/mol
XLogP3
1.900
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
1
Exact Mass
260.012 Da
Monoisotopic Mass
260.012 Da
Topological Polar Surface Area
42.400 Ų
Heavy Atom Count
16
Formal Charge
0
Complexity
249.000
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
Lösungsrechner
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Application Protocols
No standardized biological or analytical application protocols are specified for this item. Typical usage is as a synthetic building block/intermediate.
General laboratory practices (literature/general guidance):
Stock solutions: Prepare at 10–100 mM in dry DMSO or DMF for screening chemistry; filter (0.2 µm PTFE) if needed.
Reaction setup: For SNAr or cross-couplings, dry glassware, inert atmosphere (N2/Ar), anhydrous solvents, and calibrated stirring/heating are recommended. Monitor by TLC or LC–MS.
Analytical characterization: 1H/13C NMR in DMSO-d6 or CDCl3 as soluble; LC–MS with ESI positive mode typically provides clear [M+H]+ for heteroaromatic amides.
For any assay-specific procedures, develop and validate methods tailored to your system. Refer to the CoA/SDS for handling constraints.
Biological Roles
This product is a synthetic heteroaromatic amide intended for research and laboratory use only. No endogenous biological role is established for 4-(2,6-Dichloroisonicotinoyl)morpholine.
General context (literature/general knowledge):
Heteroaromatic amides and substituted pyridines are common motifs in chemical biology probes and medicinal chemistry, often used to tune lipophilicity, basicity, and binding geometry. However, any bioactivity of this specific compound would be context-dependent and must be determined experimentally.
The pyridine nitrogen can be protonated in physiological-like media, potentially affecting membrane permeability and solubility; morpholine is likewise a commonly used solubilizing/basic moiety in probe design.
Important caveat:
No biological function, target engagement, ADME, or toxicity profile is specified for this item. Any exploration of biological effects should be undertaken strictly as research, with appropriate controls and risk assessments.
Compliance note:
For research use only. Not for human or veterinary use, not for diagnostic procedures, and not for clinical applications.
Buffer Applications
This compound is not a buffering agent and is not typically used to prepare laboratory buffers.
If dissolution for biological assays is required, researchers commonly prepare stock solutions in DMSO or DMF and dilute into assay media with attention to final cosolvent percentage (literature/general practice).
For pH control, use established biological buffers (e.g., phosphate, HEPES, MOPS). This product does not substitute for those systems.
Item-specific buffer formulations, pKa values, or buffering ranges: Not applicable/not specified for this item.
Green Alternatives
Selecting greener media and conditions can reduce environmental impact without sacrificing performance (literature/general guidance).
Greener solvent options for typical transformations:
Replace DMF/DMSO with: Cyrene, propylene carbonate, dimethyl carbonate, or 2-MeTHF where compatible with reagents.
Replace dioxane/toluene with: 2-MeTHF, CPME, or ethyl acetate for many couplings and SNAr.
Aqueous micellar catalysis (e.g., TPGS-750-M) can enable couplings in water-rich media.
Comparison (general):
DMF vs Cyrene: Cyrene offers similar polarity with improved biodegradability but can be less stable to strong bases; evaluate base strength and temperature.
Dioxane vs 2-MeTHF: 2-MeTHF provides lower toxicity and renewable sourcing; adjust for water content and peroxides (perform peroxide test and inhibitor management for ethers).
Toluene vs EtOAc: Ethyl acetate is biodegradable and less toxic; may require temperature optimization due to lower boiling point.
Other green practices:
Ligand/catalyst economy: Use modern ligand systems enabling low Pd loadings (≤0.5 mol%) and room-temperature couplings where feasible.
Base selection: Favor inorganic carbonates/phosphates over strong alkoxides to reduce hazards.
Workup minimization: Use solvent-switch crystallizations or in-pot salt formations to avoid chromatographic silica waste.
Note: Validate solvent/catalyst substitutions at small scale to confirm yield and selectivity parity with traditional conditions.
Pharmaceutical Uses
No pharmacopeial status or excipient role is specified for this item; it is supplied for research use only.
General context (literature/general knowledge):
Substituted pyridyl amides such as 4-(2,6-dichloroisonicotinoyl) derivatives are frequently encountered as synthetic intermediates or SAR analogs during preclinical hit-to-lead optimization. They may serve as protected or solubilizing variants of acid-derived fragments.
Morpholine is a common polarity- and pKa-modulating group in discovery chemistry, often improving solubility and metabolic profiles; however, that does not imply suitability as a pharmaceutical ingredient for this specific compound.
For formulation screening in discovery, DMSO stock solutions and subsequent dilution into aqueous media (with surfactants or cyclodextrins if needed) are typical approaches to enable in vitro testing.
Regulatory note:
Not listed with compendial monographs (USP/EP/JP) for any excipient or API use to our knowledge. Any GMP/CMC applicability would require separate qualification and is outside the scope of this research-only product.
Physical Properties
Item-specific physicochemical specifications were not provided in the 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.
Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
Melting point (MP): Not specified for this item; refer to CoA/Spec Sheet.
Boiling point (BP): Not specified for this item; refer to CoA/Spec Sheet.
Density: Not specified for this item; refer to CoA/Spec Sheet.
Refractive index: Not applicable/unused for solids; if liquid, Not specified for this item; refer to CoA/Spec Sheet.
Solubility: Item-specific solubility not reported. As a general guide for amide-linked heteroaromatics, good solubility is often observed in polar aprotic solvents (DMSO, DMF, NMP) and moderate in ethyl acetate and acetonitrile; limited aqueous solubility is typical unless protonated (literature/general guidance).
pKa/logP: Not specified for this item; refer to CoA/Spec Sheet. For related 2,6-dichloropyridyl amides, the pyridine nitrogen can be protonated under acidic conditions, increasing water solubility (literature/general guidance).
Important: Treat any literature/general values as guidance only. For process design, chromatography, or formulation work, obtain and use the lot-specific CoA/Spec Sheet.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and implications (general guidance):
If provided as “research grade,” the material is intended for synthetic and analytical research only and is not certified for clinical, diagnostic, or GMP manufacturing use. This listing is labeled For research use only.
If a specific assay purity (e.g., ≥98% by HPLC/GC/NMR) is listed on the CoA, it reflects the main-component purity excluding volatile solvents and water. Isomeric and inorganic impurities, as applicable, should be detailed on the CoA/Spec.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet. In the absence of stabilizers, standard storage in closed containers under ambient conditions is typically adequate for neutral amides, but confirm stability in your matrix.
Trace analyses: Water content, residual solvents, and elemental impurities are lot-dependent. Not specified for this item; refer to CoA/Spec Sheet for Karl Fischer, residual solvent, and metal screening results when available.
Documentation:
Each lot should ship with or have access to a CoA detailing assay method, impurity profile, and key test limits. Request additional QC data (NMR, LC–MS, HRMS) as needed for regulated or scale-up workflows.
Reaction and Applications
As a 2,6-dichloro-substituted isonicotinoyl morpholine, this molecule is a versatile heteroaromatic scaffold. While the amide itself is generally robust, the dichloro-pyridine ring and basic heteroatoms enable several transformations (literature/general guidance):
Nucleophilic aromatic substitution (SNAr): The 2- and 6-chloro substituents on a pyridine ring (activated by the ring nitrogen) can undergo SNAr with amines, thiols, or alkoxides under heating and base (e.g., K2CO3, Cs2CO3) in polar aprotic solvents (DMF/DMSO). This enables rapid diversification at the 2/6 positions.
Cross-coupling: Aryl chlorides on electron-deficient pyridines participate in Pd-catalyzed Suzuki–Miyaura, Buchwald–Hartwig, and Stille couplings with appropriate ligands (e.g., BrettPhos/XPhos/DavePhos) to install aryl, heteroaryl, or amine substituents.
Salt formation and crystallization: Protonation of the pyridine nitrogen forms crystalline salts (e.g., HCl, TsOH), aiding purification or polymorph studies.
Amide stability: The N-acyl morpholine amide is typically stable toward many conditions used in cross-couplings; hydrolysis or transamidation requires stronger reagents (acid/base, activating agents) and is uncommon under mild coupling conditions.
Medicinal chemistry: The scaffold supports vector growth in two ortho positions to the ring N, providing useful 3D exit vectors and modulating electronics via the ring nitrogen and amide carbonyl.
Probe/intermediate synthesis for structure–activity relationship (SAR) campaigns
Model substrate for studying reactivity of 2,6-dichloropyridines
Reaction Conditions
General literature guidance for transformations applicable to 2,6-dichloropyridyl amides (not item-specific specifications):
SNAr substitutions:
Solvent: DMF, DMSO, or NMP.
Base: K2CO3, Cs2CO3, or NaH (for alkoxides); DIPEA for milder aminations.
Temperature: 80–140 °C depending on nucleophile strength and substitution pattern.
Time: 2–24 h; monitor by LC–MS or HPLC.
Tips: Excess nucleophile or in situ generation (e.g., thiolate from thiol + base) often accelerates reactions. Water traces can inhibit some SNAr—ensure dry conditions.
Suzuki–Miyaura coupling (for C–Cl activation on electron-poor pyridines):
Catalyst: Pd(PPh3)4 (2–5 mol%) or Pd2(dba)3 (1–2 mol%) with Buchwald-type ligands (XPhos, SPhos).
Base: K3PO4, Cs2CO3, or Na2CO3 (aq/organic biphasic or anhydrous).
Solvent: 1,4-dioxane, 2-MeTHF, toluene/H2O, or DMAc.
Temperature: 80–110 °C.
Notes: Electron-deficient chloropyridines couple efficiently with appropriate ligands; add water (5–10%) to enhance boronate transmetalation when compatible.
Buchwald–Hartwig amination:
Catalyst/ligand: Pd2(dba)3 (1–2 mol%) + BrettPhos or RuPhos; or Pd-PEPPSI-type systems for aryl chlorides.
Base: NaOtBu, KOtBu, or K3PO4.
Solvent: Toluene, dioxane, or CPME.
Temperature: 80–110 °C.
Workup/purification:
Quench with water/brine; extract with EtOAc or DCM.
Purify by silica chromatography (DCM→DCM/MeOH or EtOAc/hexanes) or crystallization from EtOAc/MeOH.
All parameters are literature-style starting points; optimize for your substrate/catalyst system.
Safety and Handling
Hazard classification details were not provided in the Product Data for this item. Always consult the SDS for authoritative and up-to-date safety information.
GHS/CLP: Not specified for this item; refer to SDS.
Signal Word / H-Statements / Pictograms: Not specified for this item; refer to SDS.
General laboratory precautions for chlorinated heteroaromatic amides (literature/general guidance):
Expected hazards: May cause skin and eye irritation and may be harmful if swallowed or inhaled. Dust can be irritating to the respiratory tract.
PPE: Wear lab coat, safety glasses or face shield, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a well-ventilated fume hood to avoid inhalation of dust or vapors.
Incompatibilities: Avoid strong oxidizing agents and strong bases/acids that could lead to decomposition or hydrolysis of the amide under forcing conditions. Store away from moisture if hydrolysis sensitivity is a concern.
First aid (overview): If inhaled, move to fresh air; if on skin, wash with soap and water; if in eyes, rinse cautiously with water for several minutes; if ingested, rinse mouth and seek medical attention. Always follow site SOPs.
Spills: Avoid dust generation, collect with inert absorbent, and dispose according to local regulations.
Thermal decomposition: Organic chlorinated compounds may release HCl and other irritants upon burning; use appropriate firefighting measures (CO2, dry chemical, foam) and SCBA.
Note: The above is general guidance. Rely on the product SDS for specific hazard statements and response measures.
Solvent Selection
This compound is a heteroaromatic amide with a basic pyridine nitrogen and a morpholine auxiliary, imparting moderate polarity and hydrogen-bonding capacity.
General miscibility/solubility tendencies (literature/general guidance):
High solubility: DMSO, DMF, NMP.
Moderate solubility: Acetonitrile, ethyl acetate, dichloromethane, methanol/ethanol (especially when protonated).
Low solubility: Nonpolar alkanes and ethers (e.g., heptane, MTBE) unless warmed or co-solvented.
Aqueous media: Limited at neutral pH; solubility increases under acidic conditions (pyridinium salt formation).
Polarity class and use:
Polar aprotic-compatible substrate; ideal for SNAr or cross-coupling conditions that favor high-dielectric solvents (e.g., DMAc, DME/Dioxane with co-solvents).
Comparison (general):
DMSO vs DMF: DMSO often gives higher solubility for highly polar amides; DMF can be advantageous for base-mediated SNAr; both require rigorous drying for air/moisture-sensitive transformations.
Acetonitrile/EtOAc: Preferred for workup and crystallization screens due to moderate polarity and volatility.
Practical tips:
If LC analysis is required, choose HPLC-grade solvents with low UV background. For salt-formation to aid solubility, add 0.1% TFA or HCl to protic/aqueous eluents.
For scaling purifications, EtOAc/hexanes or DCM/MeOH gradients often provide good selectivity for heteroaromatic amides.
Storage and Reconstitution
Storage and shipping (Product Data):
Storage Conditions: Room temperature.
Shipped In: Normal.
Additional guidance (general best practices for neutral amides and heteroaromatics):
Container: Store in a tightly closed, chemically compatible container (amber glass recommended) to limit moisture and light exposure.
Environment: Keep in a dry place; avoid excessive heat and direct sunlight. Use desiccant in the storage cabinet if ambient humidity is high.
Stability: Neutral amides are generally stable at ambient conditions; avoid prolonged exposure to strong acids/bases which can promote hydrolysis.
Reconstitution/dissolution:
Solvent selection: For stock solutions, use dry DMSO, DMF, or acetonitrile. Sonication and gentle warming (≤40 °C) can aid dissolution. For aqueous use, prepare an organic stock and dilute into buffered media; slight acidification (e.g., 0.1% HCl) may improve solubility via pyridine protonation.
Filtration: If particulates remain, sterile-filter through a 0.2 µm PTFE or PVDF membrane (avoid cellulose esters with strong solvents).
Freeze–thaw: If preparing aliquots of DMSO solutions, store at −20 °C to minimize degradation; avoid repeated freeze–thaw by aliquoting.
Always consult the lot-specific CoA and SDS for definitive handling, storage limits, and compatibility information.
Structure and Identity
A dichloro-substituted pyridine amide bearing a morpholine moiety; useful as a heteroaromatic scaffold for synthesis and SAR exploration.
InChIKey: 6301 (Product Data; appears abbreviated; full InChIKey not specified for this item; refer to CoA/Spec Sheet.)
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 based on the name, literature):
Core ring system: a pyridine (isonicotinoyl = pyridine-4-carbonyl) ring bearing chlorine substituents at the 2- and 6-positions (literature/structure inference).
Functional groups: an amide linkage connecting the 4-pyridinecarbonyl to a morpholine nitrogen (N-acyl morpholine) (literature/structure inference).
Heteroatoms: ring nitrogen (pyridine), amide carbonyl oxygen, morpholine oxygen, and morpholine nitrogen.
2D topology in words: a 2,6-dichloro-4-pyridinecarbonyl group attached via C=O–N to the morpholine ring. The morpholine is a six-membered heterocycle with alternating –CH2– units and embedded O and N atoms opposite each other (literature/structure inference).
Notes:
Stereochemistry: none expected (no stereocenters) (literature/structure inference).
For definitive identifiers (full InChI, SMILES, exact elemental composition), consult the CoA/Spec Sheet for this specific lot.
Synthetic Utility
Key functional elements and reactivity (literature/general guidance):
Electrophilic aryl chloride positions (2,6) on the pyridine ring: amenable to SNAr with hard nucleophiles or to Pd-catalyzed couplings (Suzuki, Buchwald–Hartwig, Stille, Negishi). Electron-deficient pyridines enhance leaving-group departure.
Amide linkage (N-acyl morpholine): robust under many cross-coupling conditions, allowing orthogonal diversification on the ring before any amide modification. Under forcing conditions, can be hydrolyzed or engaged in transamidation after activation.
Basic sites: pyridine nitrogen and morpholine nitrogen (amide-bound) influence coordination and can transiently interact with catalysts, sometimes requiring ligand/base/catalyst tuning to maintain activity.
Retrosynthetic value:
Serves as a linchpin: starting from this scaffold, rapid elaboration at positions 2 and/or 6 provides multiple vectors while conserving the isonicotinoyl-morpholine pharmacophore.
Can be traced back to 2,6-dichloroisonicotinic acid (or acid chloride/activated ester) and morpholine; thus it can also be a benchmark substrate to optimize acylation and coupling sequences.
Representative transformations:
2- or 6-substitution via SNAr with anilines/aliphatic amines, thiolates, or alkoxides.
Suzuki–Miyaura to install (hetero)aryl groups using boronic acids/esters.
Buchwald–Hartwig amination to append amines with tailored ligands (BrettPhos/XPhos).
Outcome: A tractable platform for library synthesis and diversification in heteroaryl chemistry.
Target Specificity
Not applicable. This product is a small-molecule research chemical, not a biological macromolecule or affinity reagent. No target, antigen, isotype, or species reactivity information is provided or implied for this item.
Häufig gestellte Fragen
How should this product be stored?
Store at room temperature.
How is this product shipped?
This product ships under standard ambient conditions. No temperature-controlled packaging is required.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 57803-44-8, the molecular formula is C10H10Cl2N2O2, and the molecular weight is 261.1 g/mol. InChIKey AIIGKPCMCFGSPV-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.
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