This compound belongs to the class of organic compounds known as pyridinecarboxylic acids. These are compounds containing a pyridine ring bearing a carboxylic acid 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
212.160 g/mol
XLogP3
0.800
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
3
Exact Mass
212.043 Da
Monoisotopic Mass
212.043 Da
Topological Polar Surface Area
94.200 Ų
Heavy Atom Count
15
Formal Charge
0
Complexity
252.000
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
No vendor-validated biological application protocols (e.g., WB, IHC, IF, FC) apply to this small-molecule building block.
General synthetic handling tips (literature/good practice):
Weigh and transfer quickly to minimize exposure to ambient moisture when planning moisture-sensitive steps (e.g., acid chloride formation, BBr3 demethylation).
Verify identity (1H/13C NMR, LC–MS) on receipt; establish an HPLC method (e.g., C18, 60:40 MeCN:H2O with 0.1% formic acid) for routine assay monitoring.
For hydrogenations, pre-wet Pd/C and perform a small-scale safety test to evaluate exotherm and gas uptake.
For detailed, step-by-step procedures tailored to your route, consult primary literature and adapt to your specific equipment and safety standards.
Biological Roles
This product is intended for research use as a synthetic intermediate. No biological activity or clinical use is claimed.
General/literature context for the scaffold (not item-specific claims):
Nicotinate (pyridine-3-carboxylate) motifs are structurally related to niacin derivatives; however, nitro- and methoxy-substituted esters such as this are non-natural and are used primarily as synthetic building blocks in medicinal chemistry.
The 5-nitro substituent renders the ring strongly electron-deficient, which can modulate binding characteristics of derived analogs in fragment-based lead discovery.
The ester/acid–amide interconversion pathway enables rapid access to amide-linked libraries to probe SAR against enzymes or receptors in biochemical assays.
Any testing for biological function, target engagement, or ADME properties should be designed and interpreted by qualified researchers. This product is supplied strictly for laboratory research; it is not a drug, diagnostic, or for human/animal consumption.
Buffer Applications
Not typically applicable. Methyl 2-methoxy-5-nitronicotinate is a low–water-solubility heteroaromatic ester used as a synthetic intermediate rather than as a buffering agent.
Practical note:
If aqueous work is necessary (e.g., bioconjugation to derived acids/amides), employ water-miscible co-solvents (DMSO, DMF, acetonitrile) and appropriate biological buffers (e.g., phosphate, HEPES) tailored to the reaction partners. The parent ester is not itself used to prepare biological buffers.
Green Alternatives
While the compound itself is a building block, many of its key transformations can be executed in greener media with improved process mass intensity (PMI). Below are literature/general considerations:
Greener solvent choices (examples):
Hydrogenation (nitro → amine): Prefer ethanol or isopropanol over methanol or ethyl acetate; consider water–alcohol mixtures with supported catalysts to reduce VOC use.
Ester hydrolysis: Aqueous ethanol or water/2-MeTHF biphasic systems can replace DMF/DMSO. Enzymatic ester hydrolysis (lipases) in buffered aqueous/organic systems may be viable for selective transformations.
Demethylation: Classical BBr3 in DCM is effective but not green. Alternatives include AlCl3 in toluene (still hazardous) or oxidative demethylations (e.g., CAN-mediated) where compatible, though scope may be limited. Evaluate ionic liquids or sulfolane cautiously.
Couplings: Replace dioxane/DMF with 2-MeTHF, CPME, propylene carbonate, or Cyrene when catalyst/ligand systems tolerate them.
Trade-offs and risk notes:
Solubility and rate may decrease in greener solvents; adjust temperature, catalyst loading, or concentration accordingly.
Workup and isolation: Greener solvents like 2-MeTHF and CPME often enable efficient aqueous workup and easy solvent recovery via low azeotrope formation.
Mini comparison (general):
DMF/DMSO: Excellent solubility/kinetics; regulatory and EHS concerns.
2-MeTHF/CPME: Biobased or low peroxide formation; good for extractions/couplings; flammable.
Ethanol/water: Benign, inexpensive; may promote side reactions (transesterification/hydrolysis) — leverage intentionally or mitigate.
Pharmaceutical Uses
No excipient or pharmacopeial role is specified for this item; it is supplied for research use only.
General R&D context (not a therapeutic claim):
Heteroaromatic nicotinate esters serve as versatile intermediates in early-stage drug discovery and process development, enabling rapid access to acid, amide, anilide (after nitro reduction), and ether/phenol derivatives.
The scaffold may be incorporated into screening libraries or used to explore electronic effects of nitro/amide substitutions on potency and selectivity.
Regulatory note:
This material is not listed here with any pharmacopoeial monograph and is not intended for human or veterinary use. For any GMP-related development, source appropriate grade and supporting documentation.
Physical Properties
Item-specific specs:
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general expectations for this structural class (informational only, not item specifications):
State/appearance: Substituted nitro-nicotinate esters are commonly solids at ambient temperature and may present as pale yellow to yellow crystalline materials due to the nitro-substituted heteroaromatic chromophore.
Solubility profile: Typically soluble in polar aprotic organic solvents (e.g., acetonitrile, DMF, DMSO, dichloromethane, THF) and esters; sparingly soluble in water due to ester and aromatic ring.
UV/Vis: Nitro-heteroaromatics show strong absorption in the near-UV; exact maxima depend on substitution.
Acid/base behavior: The pyridine nitrogen is weakly basic (ring deactivated by nitro and ester), and the ester is neutral; no readily ionizable acidic protons under neutral conditions.
Handling-relevant traits (general):
Thermal behavior: Aromatic esters are generally stable below 150–200 °C; nitro groups can lower thermal stability—avoid overheating.
Hygroscopicity: Not typically hygroscopic, but dryness is recommended for moisture-sensitive transformations (e.g., coupling or metal-catalyzed steps).
For authoritative, lot-specific values (mp, bp, density, refractive index, water content, residual solvent): refer to the product’s CoA/Specification Sheet.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on grades for heteroaromatic building blocks (general):
Research grade: Suitable for most synthetic and screening applications. Typical acceptance criteria include NMR purity, HRMS match, and controlled residual solvents; check CoA for actual values.
High-purity/Screening grade: Emphasizes high assay (e.g., >98% by HPLC/GC), narrow impurity profile, and consistent performance in parallel synthesis.
Chromatography-grade attributes (if applicable): Low UV baseline-absorbing impurities for photometric detection—relevant when using in photochemical or analytical contexts.
Impurity considerations (general):
Likely impurities: Regioisomeric nicotinate esters, hydrolysis products (nicotinic acid derivatives), residual nitration or O-methylation by-products, and residual inorganic salts.
Stabilizers: None typically required for this class; if used, they would be disclosed on the CoA.
Best practices:
Verify identity and purity by orthogonal methods (1H/13C NMR, LC–MS, HPLC area%).
For sensitive transformations (e.g., catalytic hydrogenation), consider pre-drying under vacuum and checking for peroxides in solvents rather than in the solid.
For this specific SKU (M1065722), rely on the Aladdin CoA/Spec Sheet for assay, residual solvents, water content (Karl Fischer), and detailed impurity limits.
Reaction and Applications
This multifunctional scaffold offers orthogonal handles for diversification (general/literature guidance):
Nitro-to-amine conversion: Selective reduction (H2/Pd–C, Fe/AcOH, SnCl2/HCl) affords the 5-aminonicotinate, enabling subsequent acylation, sulfonylation, or diazotization for further diversification.
Ester transformations: The methyl ester allows hydrolysis to the corresponding acid (for amide coupling), alcoholysis (transesterification to other esters), or conversion to acid chloride (SOCl2, (COCl)2) for in situ coupling.
2-Methoxy as a masked hydroxyl: Demethylation (e.g., BBr3) yields the 2-hydroxynicotinate, enabling O-alkylation, O-acylation, or tautomeric access to 2-pyridone-like reactivity under certain conditions.
N-oxidation and further ring chemistry: Formation of the N-oxide (m-CPBA) can activate the ring for rearrangements or directed substitutions; subsequent deoxygenation (PCl3, Zn/AcOH) restores the pyridine.
Cross-coupling strategies: Installation of halogens (e.g., via diazotization from the aniline derivative or via directed lithiation/borylation after protecting groups) allows Suzuki–Miyaura, Buchwald–Hartwig (from anilines), and other Pd-catalyzed couplings.
SNAr on activated positions: While methoxy is not a classical leaving group, highly activated pyridine rings may undergo methoxy displacement by strong nucleophiles or after prior activation (e.g., conversion to a better leaving group).
Use cases (typical):
Library generation in medicinal chemistry leveraging the amine (from nitro reduction) and acid/amide manifold.
Synthesis of ligands and heteroaromatic fragments where electronic tuning via nitro/amide/ether modifications is desired.
All examples are general literature practices; adjust based on substrate reactivity and catalyst system.
Reaction Conditions
General literature conditions for common transformations of nitro-nicotinate esters (guidance only; optimize per substrate and scale):
Nitro reduction → aniline:
H2 (1–5 bar) over 5–10% Pd/C in EtOH or EtOAc, 20–40 °C, 2–12 h. Monitor by LC–MS; avoid over-reduction of the pyridine ring.
Alternative: Fe powder (3–5 equiv) in AcOH or NH4Cl/H2O–EtOH, 50–80 °C, 2–6 h; or SnCl2·2H2O (2–3 equiv) in EtOH/HCl.
Ester hydrolysis (saponification):
NaOH (1–2 equiv) in THF/H2O (1:1 to 3:1), 25–60 °C, 1–6 h; acidic workup to isolate the acid.
Acidic hydrolysis: Aqueous HCl (3–6 M) in dioxane/H2O, reflux, 2–6 h (may be slower).
Ester reduction:
DIBAL-H (1.2–1.5 equiv) in toluene or DCM at −78 to −20 °C for aldehyde stage; quench carefully to suppress over-reduction.
LiAlH4 (2–3 equiv) in THF, 0–25 °C to reflux, 1–4 h yields primary alcohol.
O-Demethylation (2-OMe → 2-OH):
BBr3 (1–3 equiv) in anhydrous DCM or toluene, −78 to 0 °C then to rt, 2–16 h; strictly anhydrous. Quench cautiously.
Amide coupling (from acid):
HATU (1.1–1.5 equiv), DIPEA (2–3 equiv) in DMF/2-MeTHF, 0–25 °C, 1–4 h; or EDC·HCl/HOBt in DCM/DMF.
Notes:
The electron-deficient ring often improves rates of hydrogenation of the nitro group; protect the ester if reduction conditions jeopardize it.
Monitor for potential transesterification or hydrolysis in alcoholic solvents; adjust pH and time accordingly.
Safety and Handling
Item-specific hazard data from Product Data:
Signal word: Not specified for this item; refer to SDS.
H-statements / GHS classification / Pictograms: Not specified for this item; refer to SDS.
General safety considerations for nitro-substituted pyridine esters (informational; defer to SDS):
Likely hazards: Organic nitro compounds and aromatic esters may cause eye/skin irritation and may be harmful if swallowed or inhaled. Dust may form explosive mixtures in air; minimize dust generation.
PPE: Use appropriate PPE including lab coat, nitrile gloves, and safety glasses or goggles. Handle in a fume hood to avoid inhalation of dust or vapors during reactions.
Incompatibilities: Avoid strong bases for extended periods (ester saponification), strong acids (hydrolysis), strong reducing agents at elevated temperature (risk of uncontrolled nitro reduction), and strong oxidizers.
Special risks: Nitro group reduction is exothermic; control addition of reducing agents and temperature. Avoid overheating and open flames. While not an ether, avoid prolonged storage with strong bases that can induce transesterification.
First aid (overview):
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation develops.
Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
Always consult the product SDS for definitive hazard classification, exposure limits, spill response, waste disposal, and transport information.
Solvent Selection
Applicability: This product is a heteroaromatic ester building block, not used as a solvent. Selection here refers to solvents suitable for dissolving it and for performing common reactions on it.
General solubility/miscibility guidance (literature/general):
Polar aprotic solvents: DMSO, DMF, DMAc, NMP, and acetonitrile typically provide high solubility for nitro-pyridine esters—useful for SNAr-like substitutions on activated positions and for coupling reactions.
Moderately polar organics: Dichloromethane, ethyl acetate, THF, and 2-MeTHF often dissolve nicotinate esters and are appropriate for extractions and chromatographic purification.
Alcohols: Methanol/ethanol can be used for solvolysis or hydrogenation media but may promote transesterification under basic or acidic conditions.
Aqueous media: Limited solubility is expected; use co-solvents or phase-transfer strategies when required.
When to choose what (practical tips):
Reduction of nitro group: Ethanol, methanol, or ethyl acetate under H2/Pd-C are common; for higher solubility, switch to EtOH/THF or EtOAc/MeOH blends.
Ester hydrolysis: THF/H2O, dioxane/H2O, or MeOH/H2O mixtures with base (NaOH, K2CO3) or acid catalysis.
Demethylation of 2-methoxy: Non-protic chlorinated solvents (DCM, toluene) are preferred with BBr3/AlCl3; strictly anhydrous conditions required.
Cross-coupling on further-functionalized analogs: If a halide is introduced, use dioxane, toluene, or 2-MeTHF with Pd catalysis.
Note: Verify solvent compatibility with planned reagents and catalysts; ensure water content and amine/acid impurities are controlled for moisture- or acid/base-sensitive steps.
Storage and Reconstitution
Item-specific storage and shipping:
Storage Conditions: Room temperature (per Product Data).
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
General storage guidance for nitro-heteroaromatic esters:
Keep container tightly closed in a dry, well-ventilated place. Protect from excessive heat and prolonged exposure to light.
If long-term storage is anticipated, consider storing in an amber glass bottle with desiccant. Avoid persistent exposure to strong acids/bases which can promote hydrolysis or transesterification.
No reconstitution is typically required; dissolve directly in a suitable anhydrous organic solvent (e.g., DMSO, DMF, acetonitrile, DCM) immediately before use.
For stock solutions: Prepare under dry, inert atmosphere if reactions are moisture-sensitive. Store solutions at 2–8 °C when feasible and use within a few days; check for precipitation or degradation by LC–MS/HPLC prior to use.
Always consult the product’s CoA and SDS for container compatibility, stability data, and any additional handling requirements.
Structure and Identity
Brief overview: Methyl 2-methoxy-5-nitronicotinate is a substituted nicotinate (pyridine-3-carboxylate methyl ester) bearing a methoxy group at the 2-position and a nitro group at the 5-position, yielding an electron-deficient, multifunctional heteroaromatic ester useful as a building block.
Item-specific (from Product Data):
CAS: 122433-50-5
PubChem CID: 14371731
InChIKey: 67286 (as provided)
Storage: Room temperature
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 name; literature):
Core ring: Pyridine (six-membered aromatic ring with one ring nitrogen).
Carboxylate function: Methyl ester at the 3-position ("nicotinate").
Substituents: 2-methoxy (–OCH3) and 5-nitro (–NO2) on the ring.
Functionality profile: Contains an electron-withdrawing nitro group and an ester; 2-methoxy is a masked 2-hydroxy handle (demethylatable) adjacent to ring nitrogen.
2D structural description (general): A pyridine ring with N at position 1; at C-3 a –C(=O)OCH3 ester; at C-2 an –OCH3 substituent; at C-5 a –NO2 group. No stereocenters; fully aromatic.
Synthetic Utility
Functional group leverage (literature/general):
Ester handle (–CO2Me at C-3):
Hydrolysis to acid for subsequent amide coupling (EDC/HOBt, HATU, CDI) or Curtius/Schmidt rearrangements.
Alcoholysis/transesterification to tune protecting groups or solubility.
Reduction to benzyl-like alcohols (DIBAL-H for aldehyde stage; LiAlH4/NaBH4–iodide systems for alcohol).
Nitro group (C-5 –NO2):
Chemoselective reduction to an aniline (H2/Pd–C, Fe/AcOH), enabling urea, sulfonamide, or diazonium chemistry (Sandmeyer-type diversifications after diazotization).
Nucleophilic additions under specific conditions (e.g., Nef/related pathways after conversion to oxime/imine on derivative substrates).
2-Methoxy (C-2 –OMe):
Demethylation to 2-hydroxynicotinate (BBr3, AlCl3) for O-derivatization or tautomeric 2-pyridone chemistry.
Potential leaving group under strong activation for SNAr-type substitutions, especially after converting –OMe to a better leaving group (e.g., –OTf from the phenol stage).
Ring nitrogen (pyridine N):
N-oxidation (m-CPBA) to direct further functionalization; quaternization (MeI, MeOTf) to tune electronics/solubility.
Retrosynthetic value:
Serves as a convergent node where orthogonal modifications (nitro reduction vs. ester hydrolysis vs. O-demethylation) can be sequenced with high chemoselectivity, enabling rapid analog generation with minimal protecting group manipulations.
Target Specificity
Not applicable. This product is a small-molecule building block, not a biological macromolecule or affinity reagent. No antigen/epitope/clone/isotype information applies.
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