6-Nitronicotinaldehyde - ≥97% , CAS No.1804410-06-7

CAS: 1804410-06-7 Cat. No.: N971545 Fórmula: C₆H₄N₂O₃ Peso molecular: 152.110

GRADE & PURITY ≥97%

Storage

Room temperature

Specifications

Especificaciones y pureza

≥97%

Condiciones de almacenamiento de almacenamiento

Room temperature

Pureza

≥97%

Nombres e identificadores

• Sonrisas canónicas: C1=CC(=NC=C1C=O)[N+](=O)[O-]
• IUPAC Name: 6-nitropyridine-3-carbaldehyde
• InChIKey: FJIUIBAOGRIIDR-UHFFFAOYSA-N
• INCHI: 1S/C6H4N2O3/c9-4-5-1-2-6(7-3-5)8(10)11/h1-4H
• Peso molecular: 152.110

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Clase Pyridines and derivatives
      • Subclass Pyridine carboxaldehydes

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Clase: Pyridines and derivatives
• Subclass: Pyridine carboxaldehydes
• Intermediate Tree Nodes: Not available
• Direct Parent: Pyridine carboxaldehydes
• Alternative Parents: Nitroaromatic compounds Aryl-aldehydes Imidolactams Heteroaromatic compounds Propargyl-type 1,3-dipolar organic compounds Organic oxoazanium compounds Azacyclic compounds Organonitrogen compounds Organic salts Organic oxides Hydrocarbon derivatives Organic cations
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Nitroaromatic compound - 3-pyridine carboxaldehyde - Aryl-aldehyde - Imidolactam - Heteroaromatic compound - C-nitro compound - Organic nitro compound - Organic oxoazanium - Allyl-type 1,3-dipolar organic compound - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Azacycle - Organic oxide - Organic oxygen compound - Organooxygen compound - Organic nitrogen compound - Aldehyde - Organic salt - Hydrocarbon derivative - Organonitrogen compound - Organic cation - Aromatic heteromonocyclic compound
• Descripción: This compound belongs to the class of organic compounds known as pyridine carboxaldehydes. These are aromatic compounds containing a pyridine ring which bears a carboxaldehyde group.
• External Descriptors: Not available

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Propiedades químicas y físicas

• Peso molecular: 152.110 g/mol
• XLogP3: 0.500
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 152.022 Da
• Monoisotopic Mass: 152.022 Da
• Topological Polar Surface Area: 75.800 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 166.000
• 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

Application Protocols

Not applicable as a validated bioassay reagent. No tested applications (e.g., WB, IHC, IF, FC) or recommended dilutions are provided for this small-molecule building block. For synthetic applications, see the Reaction Conditions and Synthetic Utility sections for general literature guidance.

Biological Roles

This product is a synthetic heteroaromatic building block and is not known as a natural metabolite or cofactor.

General considerations (non-clinical, research context only):

• The nicotinyl (pyridine-3-) motif occurs in biological molecules (e.g., nicotinamide derivatives), but 6-nitro substitution and the free aldehyde are not typical in vivo.
• In chemical biology, aldehyde-bearing heteroaromatics may be used as reactive handles for covalent capture (e.g., imine formation with amines) in probe design; however, any such use should be validated case-by-case.
• Nitro groups can alter membrane permeability and electron affinity; the compound could serve as a precursor to 6-amino analogs that more closely resemble biologically active pyridines after reduction.

No biological function, target specificity, or pharmacology is claimed for this item. For research use only (per Product Data).

Buffer Applications

Not typically applicable. 6-Nitronicotinaldehyde is not a buffering agent and does not constitute a defined acid/conjugate base pair suitable for maintaining pH. If used in biochemical assays, select an appropriate buffer (e.g., phosphate, HEPES, MOPS) compatible with aldehydes and nitroaromatics, and avoid primary amine buffers (e.g., Tris) when imine formation would interfere.

Green Alternatives

Perspective: The substrate itself is a specialized heteroaromatic building block; “green alternatives” relate mainly to solvent/base choices and chemoselective oxidants/reductants used with it.

Greener choices (literature/general):

• Solvents:
  • Replace DMF/DMSO with bio-derived or lower-toxicity media where feasible: ethanol, isopropanol, 2-MeTHF, CPME, propylene carbonate.
  • For Wittig/HWE: 2-MeTHF or CPME can substitute for THF; acetonitrile can often be replaced by EtOH for Knoevenagel.
• Oxidations of the aldehyde to acid:
  • Use NaClO2 (buffered) or Oxone/TEMPO systems in aqueous alcohols rather than chromium(VI) reagents.
• Reductions:
  • Catalytic hydrogenation (H2/Pd/C) in EtOH/EtOAc is preferable to stoichiometric tin salts; for reductive amination, NaBH(OAc)3 in toluene/EtOH is milder than NaBH3CN in MeCN.
• Water removal:
  • Employ molecular sieves instead of azeotropic reflux when possible.

Trade-offs:

• Solubility constraints in greener solvents may reduce rates or yields; screen mixed solvent systems (e.g., EtOH/MeCN, 2-MeTHF/EtOH).
• Nitro reduction under hydrogenation may also reduce the aldehyde; consider temporary protection (acetal) or chemoselective transfer hydrogenation protocols.

Small comparison (general):

• THF vs 2-MeTHF: similar polarity; 2-MeTHF offers higher boiling point, partial water immiscibility, and bio-based origin; may simplify extractions.
• DMF vs EtOH: EtOH is greener and easier to remove but offers lower solubility for some heteroaromatics.

Pharmaceutical Uses

No excipient or pharmacopeial role is specified for this item; refer to CoA/Spec Sheet. This compound is intended for research use only.

General process-chemistry context (literature):

• As a heteroaromatic aldehyde, it can serve as an intermediate in the synthesis of active pharmaceutical ingredient (API) candidates where a 3-formylpyridine skeleton is required.
• The nitro group provides a handle for late-stage diversification (e.g., reduction to anilines for amide coupling or heterocycle formation), enabling SAR campaigns.
• Aromatic aldehydes may also be used in prodrug or linker synthesis (e.g., oxime/imine conjugates) in early discovery chemistry, with subsequent conversion to more stable functionalities.

No therapeutic claims are made. Suitability for cGMP manufacturing would require specification, impurity control, and validation beyond the scope of this research-grade listing.

Physical Properties

Item-specific property values (bp, mp, density, RI, water/peroxide/metal limits, UV cutoff) are not specified for this item; refer to CoA/Spec Sheet.

General/literature expectations for a nitro-substituted heteroaromatic aldehyde (for method development only):

• Physical state: typically a crystalline solid at ambient temperature (literature expectation for closely related nitro-nicotinaldehydes)
• Polarity: moderately polar due to the pyridine N, aldehyde, and nitro group; strong H-bond acceptor, not an H-bond donor
• Solubility profile (qualitative, literature):
  • Good solubility in polar aprotic organic solvents (DMSO, DMF, acetonitrile)
  • Moderate solubility in alcohols and esters
  • Limited solubility in nonpolar hydrocarbons
  • Low water solubility expected
• Acid–base behavior (literature): weakly basic pyridine nitrogen (pKaH of pyridines typically ~5.0–5.5; nitro substituent further lowers basicity)
• Partitioning: electron-withdrawing nitro and aldehyde reduce hydrophobicity relative to unsubstituted alkylpyridines; logP expected in the low-to-moderate range for aromatic heterocycles (qualitative)

Practical notes:

• The aldehyde can slowly oxidize to the corresponding acid and can self-condense under basic conditions; minimize exposure to air/base and moisture during storage and handling.
• For crystallization/handling, polar aprotic solvents or alcohols are commonly suitable; confirm solvent choice on small scale first.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

Guidance on grades (general):

• Research/technical grade: typically suitable for most synthetic applications. Assay and impurity profile vary by lot.
• Analytical (AR) grade: tighter limits on inorganic/organic impurities; appropriate for analytical development and impurity-sensitive steps.
• HPLC grade (for solvents) or low-UV materials: not applicable here; however, UV background of aromatic aldehydes can be significant—use caution in trace analysis.

Stabilizers/Inhibitors: None listed for this item. In general, aldehydes are sometimes stabilized by acid traces or antioxidants; absence/presence of stabilizers can influence reactivity in base-catalyzed condensations.

Release testing typically includes identity (1H/13C NMR, IR), assay (qNMR/GC/HPLC), and residual solvents. For this item, consult the CoA for:

• Assay (%), water (Karl Fischer), residual solvents, and impurity profile
• Spectral data (NMR, MS) and chromatographic purity

Note: Select the grade that matches your application’s sensitivity to base-catalyzed side reactions and to nitro-reduction impurities.

Reaction and Applications

6-Nitronicotinaldehyde is a versatile electrophilic building block combining a heteroaromatic aldehyde (for C–C/N–C bond formation) with a strongly deactivating nitro substituent that modulates ring electronics and can be transformed orthogonally.

Key reaction families (literature/general):

• Carbon–carbon formation at the aldehyde:
  • Wittig/Horner–Wadsworth–Emmons to install alkenes (E-selectivity often favored by HWE). Solvents: THF/MeCN; bases: NaH, K2CO3, DBU.
  • Knoevenagel condensations with active methylenes (malononitrile, cyanoacetates, barbiturates) using piperidine, ammonium acetate, or amine resins in EtOH or acetonitrile.
  • Aldol-type additions from enolates, silyl enol ethers (Mukiyama aldol with Lewis acids).
• Carbon–nitrogen bond construction:
  • Imine/Schiff base formation with primary amines; subsequent reductive amination (NaBH3CN/NaBH(OAc)3) to 3-benzyl/alkyl pyridines.
• Functional group interconversions at the aldehyde:
  • Oxidation to 6-nitronicotinic acid (e.g., NaClO2/NaH2PO4; TEMPO/bleach systems) or to nitrile via oxime–dehydration sequence.
  • Reduction to alcohol (NaBH4) or to methyl via Wolff–Kishner/Clemmensen or catalytic hydrogenation sequences.
• Nitro group transformations:
  • Selective reduction to the amine (Fe/AcOH, SnCl2/HCl, Zn/NH4Cl, or H2/Pd) affording 6-aminonicotinaldehyde, enabling further cross-coupling, amide formation, or annulations.
  • N–O bond chemistry (e.g., N-oxide of pyridine) is separate; note that ring N-oxidation can further activate the ring for SNAr.
• Heteroaryl elaborations:
  • Directed metalation adjacent to the nitro or aldehyde is challenging but possible under strong base/low-temperature conditions; protect aldehyde if required.

Applications: synthesis of push–pull chromophores (via Knoevenagel), ligand scaffolds, heteroaryl vinyl derivatives, and intermediates toward nicotinamide/nicotinic acid analogs.

Practical tips:

• Dry, oxygen-limited conditions suppress aldehyde oxidation. Use molecular sieves or Dean–Stark for water-sensitive steps.
• If reducing the nitro group, protect the aldehyde (as an acetal/oxime) to avoid over-reduction.

Reaction Conditions

General literature guidance for common transformations of heteroaromatic aldehydes; adjust to your substrate and scale. Values are indicative, not item-specific specifications.

• Knoevenagel condensation:
  • Typical: aldehyde (1.0 eq), malononitrile (1.1–1.5 eq), catalytic piperidine or ammonium acetate (10–20 mol%), EtOH or MeCN, rt–60 °C, 1–6 h. Water removal (molecular sieves) can improve E selectivity/yield.
• Wittig/HWE olefination:
  • Wittig: ylide from phosphonium salt (1.1–1.5 eq) with n-BuLi/NaHMDS in THF at −78 to 0 °C; then add aldehyde; warm to 0–25 °C, 1–3 h. HWE: phosphonate (1.2–1.5 eq), base (NaH/DBU/K2CO3) in THF/MeCN, 0–25 °C, 2–6 h; often E-selective.
• Imine formation/reductive amination:
  • Aldehyde + amine (1.0–1.5 eq), 3 Å MS or Dean–Stark (toluene), 25–110 °C, then reduce with NaBH(OAc)3 (AcOH, DCE/MeOH) or H2/Pd in EtOH. Monitor to avoid over-reduction of the pyridine.
• Aldehyde reductions/oxidations:
  • NaBH4 to alcohol in MeOH/EtOH at 0–25 °C, 0.5–2 h. TEMPO/NaOCl or NaClO2 (buffered) to acid at 0–25 °C, 1–3 h.
• Nitro reduction to amine:
  • Fe/AcOH or Zn/NH4Cl in EtOH/H2O, 50–80 °C, 2–8 h; or H2 (1–3 bar)/Pd-C (5–10 wt%) in EtOH or EtOAc at rt–40 °C. Protect aldehyde (acetal) to prevent concomitant reduction.

Notes:

• The pyridine nitrogen can coordinate bases/metals; adding Lewis acids (e.g., BF3·Et2O) may activate the aldehyde toward nucleophiles but assess compatibility with nitro.
• Strictly exclude moisture and oxygen for base-sensitive steps to limit side reactions (self-condensation, oxidation).

Safety and Handling

Item-specific GHS classification, signal word, pictograms, and H-statements are not specified for this item; consult the Aladdin SDS for authoritative safety information.

General safety considerations for nitroaromatic aldehydes (literature/experience-based):

• Hazards: May cause skin/eye irritation and respiratory irritation. Nitroaromatics can present systemic toxicity upon significant exposure. Aldehydes are sensitizing/irritating and can form peroxides only rarely; the main risk is oxidation/polymerization.
• PPE: Use chemical-resistant gloves (e.g., nitrile), lab coat, safety goggles. Handle in a fume hood to avoid inhalation of dust or vapors.
• Handling:
  • Avoid heat and strong bases to limit self-condensation (aldol-type) and Cannizzaro-type side processes.
  • Keep away from strong oxidizers/reductants except when intentionally used in synthesis.
  • Minimize dust generation; weigh in a hood.
• Incompatibilities (general): strong bases, strong reducing agents (risk of exothermic reduction of nitro), strong oxidizers (over-oxidation of aldehyde), and reactive nucleophiles that can attack the aldehyde.
• First aid (overview; follow SDS):
  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: rinse with water for ≥15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
• Fire: Use CO2, dry chemical, or foam. Combustion may release NOx; firefighters should wear SCBA.

Storage per Product Data: Room temperature. Store tightly closed, in a dry, cool, well-ventilated place; protect from light and moisture to slow aldehyde oxidation. Always defer to SDS for final guidance.

Solvent Selection

This compound is a moderately polar heteroaromatic aldehyde.

• Polarity/miscibility (general):
  • Readily soluble in DMSO, DMF, NMP, acetonitrile; moderately soluble in ethanol/methanol; limited in water and nonpolar hydrocarbons.
  • Dielectric constant context (literature values for solvents): DMSO (~47), DMF (~37), MeCN (~37), EtOH (~25). These media support polar condensations (Knoevenagel, Schiff base, Wittig workups).
• When to choose specific solvents:
  • DMSO/DMF: high solubility; good for base-catalyzed condensations or SNAr attempts on activated systems.
  • MeCN/THF: suitable for Wittig/Horner–Wadsworth–Emmons (HWE) reactions; easy removal.
  • Alcohols (EtOH/MeOH/i-PrOH): useful for piperidine- or ammonium acetate-catalyzed Knoevenagel reactions and imine formations.
  • Toluene/xylene: for azeotropic water removal in imine formation under Dean–Stark; solubility may limit.

Comparison (selection tips):

• For nucleophile-addition control and minimal side reactions, dry aprotic solvents (THF, MeCN) are preferred.
• For greener profiles, EtOH or 2-MeTHF can often substitute for acetonitrile/THF, respectively, if solubility permits.

Always confirm solvent/base compatibility to avoid undesired Cannizzaro-type or polymerization pathways with aldehydes.

Storage and Reconstitution

• Storage (from Product Data): Room temperature.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Shipping: Not specified for this item; refer to CoA/Spec Sheet.

Best practices for aldehyde-containing heteroaromatics (general):

• Keep container tightly sealed, protected from moisture and light to minimize oxidation to the corresponding acid and polymerization.
• If long-term storage is anticipated, consider inert-atmosphere storage (nitrogen/argon) and placing the bottle in a desiccator with desiccant. Refrigeration is usually not required unless specified, but cooler/dry conditions can further slow degradation.
• After opening, purge headspace with inert gas and recap promptly.

Reconstitution/solution preparation (general):

• Dissolves readily in DMSO, DMF, or acetonitrile; moderately in alcohols. Use dry, oxygen-free solvents for moisture-sensitive reactions.
• Prepare stock solutions immediately before use when possible; for longer storage, aliquot under inert gas in amber vials and freeze to limit oxidation (verify stability for your conditions).

Research Use Note: For research use only (per Product Data).

Structure and Identity

Brief description: 6-Nitronicotinaldehyde is a nitro-substituted pyridine-3-carbaldehyde (nicotinaldehyde) derivative; the aldehyde is at the 3-position of the pyridine ring and the nitro group at the 6-position.

• Item-specific identifiers (from Product Data)

  • SKU: N971545
  • Product Name: 6-Nitronicotinaldehyde
  • CAS: 1804410-06-7
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Product Data lists "84281", which is not a standard InChIKey.)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Structure (literature/interpretation from name)

  • Core scaffold: pyridine ring (heteroaromatic, one ring nitrogen at position 1)
  • Substituents: aldehyde (–CHO) at C-3; nitro (–NO2) at C-6
  • Functional groups: aromatic heterocycle, aldehyde (electrophilic), nitro (strongly electron-withdrawing)
  • Stereochemistry: none (achiral)
  • 2D description: a six-membered aromatic ring with one ring N. Counting from the ring N as position 1, formyl at position 3 (meta to N), and nitro at position 6 (ortho to N, para to C-3 substituent).

• Formula & mass (computed/literature, not item-specific specs)

  • Molecular formula (literature): C6H4N2O3
  • Molecular weight (literature): ~152.11 g/mol

Note: For authoritative identity parameters used for this specific lot (e.g., exact SMILES/InChI, spectral data), refer to the product CoA/Spec Sheet.

Synthetic Utility

Functional handles and their reactivity (literature/general):

• Aldehyde (–CHO):
  • Electrophile in nucleophilic additions (cyanation, Grignard/organolithium—though ring N may require protection or Lewis acid mediation).
  • Platform for C=C construction via Wittig/HWE; for conjugated push–pull systems by Knoevenagel with donor-activated methylenes.
  • Convertible to acid, alcohol, nitrile, or amine derivatives (via oxime formation/reduction).
• Nitro (–NO2):
  • Strong –I/–M effects deactivate the ring, influencing regioselectivity and reducing basicity of the ring nitrogen.
  • Reduction to amine yields 6-aminonicotinaldehyde, opening routes to amide/urea formation, diazotization, or intramolecular cyclizations to N-containing bicyclics.
  • Can participate in nucleophilic aromatic substitution on suitably activated systems (often enhanced by pyridine N-oxide formation).
• Pyridine nitrogen:
  • Can be N-oxidized to further activate the ring toward SNAr; can coordinate to metals, enabling directed catalysis or acting as a ligand in cross-couplings of substituted congeners.

Retrosynthetic value:

• A convergent node to access 6-amino- or 6-substituted nicotinaldehydes via nitro reduction followed by derivatization.
• Entry to vinylpyridines through aldehyde-to-alkene tactics (Wittig/HWE), valuable in material and medicinal chemistry.

Protecting-group strategy:

• Protect the aldehyde as an acetal during conditions that reduce nitro or form metalated intermediates; deprotect under mild acid after transformations.

Target Specificity

Not applicable. This product is a small-molecule building block and not a biological macromolecule, antibody, or probe with defined target binding parameters. No antigen, epitope, species reactivity, clone, or isotype information is relevant.