6-Nitropyridine-2-carboxamide - ≥95% , CAS No.60278-80-0

CAS: 60278-80-0 Cat. No.: N1008317 分子式: C₆H₅N₃O₃ 分子量: 167.120

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

仕様と純度

≥95%

保管条件

Room temperature

純度

≥95%

名前と識別子

• カノニカル・スマイル: C1=CC(=NC(=C1)[N+](=O)[O-])C(=O)N
• IUPAC Name: 6-nitropyridine-2-carboxamide
• InChIKey: GKRHQIJGGWWLNL-UHFFFAOYSA-N
• INCHI: 1S/C6H5N3O3/c7-6(10)4-2-1-3-5(8-4)9(11)12/h1-3H,(H2,7,10)
• 分子量: 167.120

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • 分類 Pyridines and derivatives
      • Subclass Pyridinecarboxylic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• 分類: Pyridines and derivatives
• Subclass: Pyridinecarboxylic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Pyridinecarboxamides
• Alternative Parents: Nitroaromatic compounds 2-heteroaryl carboxamides Imidolactams Heteroaromatic compounds Primary carboxylic acid amides Propargyl-type 1,3-dipolar organic compounds Organic oxoazanium compounds Azacyclic compounds Organooxygen compounds Organonitrogen compounds Organic zwitterions Organic salts Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Pyridinecarboxamide - 2-heteroaryl carboxamide - Nitroaromatic compound - Imidolactam - Heteroaromatic compound - Carboxamide group - C-nitro compound - Organic nitro compound - Primary carboxylic acid amide - Carboxylic acid derivative - Organic oxoazanium - Azacycle - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Allyl-type 1,3-dipolar organic compound - Organic nitrogen compound - Organic zwitterion - Organic salt - Organooxygen compound - Organonitrogen compound - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Aromatic heteromonocyclic compound
• 説明: This compound belongs to the class of organic compounds known as pyridinecarboxamides. These are compounds containing a pyridine ring bearing a carboxamide.
• 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

化学的性質と物理的性質

• 分子量: 167.120 g/mol
• XLogP3: 0.200
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 167.033 Da
• Monoisotopic Mass: 167.033 Da
• Topological Polar Surface Area: 102.000 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 201.000
• 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

No assay-specific or bioanalytical protocols are provided in the Product Data for this item. For general handling:

• Prepare stock solutions in dry DMSO (e.g., 10–50 mM); filter-sterilize if required for cell-free assays; avoid prolonged aqueous exposure if solubility is limited.
• For synthetic use, follow the Reaction Conditions guidance and standard organic workup and purification protocols (crystallization, column chromatography). Consult the CoA/SDS for any special handling instructions.

Biological Roles

Applicability

• 6-Nitropyridine-2-carboxamide is a synthetic heteroaromatic compound. It is not known as an endogenous metabolite or biochemical cofactor.

General biochemical context (literature; not product-specific)

• Picolinamide motif: The 2-carboxamide on a pyridine ring can act as a bidentate hydrogen-bonding and metal-chelating motif (via ring N and carbonyl O), which is frequently used in inhibitor design and coordination chemistry.
• Nitro group: Typically introduced as a synthetic handle or electronic modulator; can be reduced in situ in biological settings to amines, but such behavior is context-dependent and not a product claim.

Usage note

• For research use only. Any biological testing or screening should ensure appropriate vehicle controls (e.g., DMSO) and solubility/aggregation assessment (e.g., light scattering, UV–vis) due to the compound’s aromatic, moderately polar nature.

Buffer Applications

This compound is not a buffering agent and is not typically used to prepare biochemical buffer systems. If solutions are needed for assays, dissolve in an appropriate co-solvent (e.g., DMSO) and dilute into the desired buffer while monitoring for precipitation. For pH control, use established buffers (e.g., phosphate, HEPES, Tris) rather than this reagent.

Green Alternatives

Context

• This item is a solid building block, not a solvent. Greener choices focus on the media and reagents used to transform or formulate it.

Greener solvent options (literature guidance)

• Replace DMF/NMP/DMAc with:
  • Cyrene (dihydrolevoglucosenone): strong dipolar aprotic character; works in many amidations and reductions; viscosity and base sensitivity can be limiting.
  • Propylene carbonate: high boiling, low toxicity; good for some nucleophilic reactions; limited miscibility with nonpolars.
  • 2-MeTHF or CPME: improved safety vs THF/Et2O; useful for extractions/recrystallizations; lower polarity may limit solubility.

Reagent alternatives

• Nitro reduction: use catalytic hydrogenation (H2, Pd/C) or transfer hydrogenation (e.g., ammonium formate) instead of stoichiometric tin chloride; minimizes heavy-metal salt waste.
• Amide dehydration: T3P or catalytic PPh3/iodinating systems with green solvents may reduce corrosive halogenated reagents (avoid POCl3/SOCl2 when possible).
• Hydrolysis: employ aqueous ethanol or water with phase-transfer/base catalysis to reduce use of strong mineral acids/bases and chlorinated solvents.

Mini-comparison (general)

• DMF vs Cyrene: similar polarity; Cyrene is biorenewable and less regulated; DMF often offers broader compatibility and lower viscosity.
• NMP vs Propylene carbonate: both high-boilers; PC is greener but may require higher temps for dissolution.

Note

• Validate solubility and reaction performance at small scale when swapping to greener media.

Pharmaceutical Uses

Item-specific (from Product Data)

• No pharmacopeial grade or excipient designation is provided. For research use only.

General context (non-clinical; not product-specific)

• Role: heteroaromatic building block for medicinal chemistry and discovery synthesis. The picolinamide motif is a common hydrogen-bonding pharmacophore and metal-binding element used to modulate potency and ADME properties in lead series.
• Formulation: as a solid research intermediate, it is not typically used as an excipient. When tested in vitro, stock solutions are commonly prepared in DMSO and diluted into assay media; solubility and stability should be verified experimentally.
• Regulatory: absent an explicit pharmacopeial listing or GMP documentation, this material should not be used in manufacturing or clinical applications.

Physical Properties

Item-specific (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.

Literature/general expectations (not product specifications)

• Empirical formula (see Structure tab): C6H5N3O3; FW ~167.12 g/mol (computed from formula).
• Physical state: typically a crystalline solid for nitro-pyridine carboxamides.
• Polarity: polar, hydrogen-bond donor (amide NH) and multiple acceptors (pyridine N, amide O, nitro O’s).
• Solubility: expected to be sparingly soluble in water; soluble in polar aprotic solvents (DMSO, DMF, NMP) and in alcohols upon warming.
• Acid/base behavior: weakly basic ring nitrogen; amide is non-basic and weakly acidic at the NH (pKa of comparable primary amides ~15–17 in DMSO; literature).
• UV characteristics: conjugated heteroaromatic; exhibits π–π* absorption in UV; exact cutoff and ε not specified.

Important

• Do not treat the above as specifications for this catalog item. For lot-specific data (mp, purity, solubility, UV, trace metals, water), consult the CoA/Spec Sheet.

Quality and Grades

Item-specific (from Product Data)

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

Guidance on interpreting grades (general)

• Research/biochemical grade: typically suitable for synthetic chemistry and discovery workflows; may not include enhanced controls on UV-absorbing impurities or trace metals unless stated.
• HPLC/LC-MS grade (when stated): indicates low UV background/low non-volatile residue; selected for analytical workflows.
• High-purity building block (when stated): emphasizes identity (>98–99%), low residual solvents, and defined impurity profiles suited to medicinal chemistry.

Stabilizers/impurity considerations

• Nitro-heteroaromatics are generally stable solids and do not typically require inhibitors. If stabilizers or special analytics (e.g., residual metals, water content by KF) are relevant, they will be listed on the CoA/Spec Sheet for this item.

Recommendation

• For regulated or sensitive applications, request the lot CoA and any available detailed specifications (purity method, residual solvents, water by KF, UV profile, trace metals).

Reaction and Applications

Focus: 6-Nitropyridine-2-carboxamide is a versatile heteroaromatic building block featuring an electron-withdrawing nitro group and a primary amide. These features enable selective transformations valuable in medicinal and materials chemistry.

Representative transformations (literature; not product-specific)

• Nitro-group reduction: to 6-aminopyridine-2-carboxamide using catalytic hydrogenation (H2, Pd/C or Raney Ni) or transfer hydrogenation; also achievable via Fe/AcOH or SnCl2/HCl. The resulting aniline-like heteroaryl amine is a handle for acylation, sulfonylation, or cross-coupling (via diazotization → Sandmeyer-type chemistry).
• Amide dehydration: conversion to the corresponding nitrile (6-nitropicolinonitrile) using SOCl2, POCl3, P2O5, or Burgess-type reagents; milder, greener options include T3P in the presence of base under azeotropic removal of water.
• Hydrolysis: amide → 2-carboxylic acid (6-nitropicolinic acid) under forcing acidic or basic conditions; subsequent activation to acid chloride allows further amide/ester formation.
• Directed metalation: the ring N and nitro group increase acidity of adjacent C–H positions; with strong bases (e.g., LDA, TMP-bases) at low temperature, lithiation can enable subsequent electrophile trapping (requires careful optimization).
• Nucleophilic aromatic substitution (VNS/SNH concepts): while nitro is not a typical leaving group, the nitro plus ring N strongly activate the ring toward nucleophilic substitution of hydrogen under specialized conditions; consult literature for substrate control.
• Cross-coupling after functional group interconversion: following nitro reduction to amine, diazotization (–N2+) can enable C–C, C–X formation (e.g., with Cu salts) on the heteroaryl core.

Applications

• Scaffold elaboration for chelating ligands (picolinamide motif), heteroaryl linkers, and H-bonding pharmacophores.
• Precursor to 6-amino derivatives used in kinase/GPCR chemical probe scaffolds and coordination complexes (general medicinal chemistry context; no clinical claims).

Reaction Conditions

General literature conditions (illustrative; optimize per substrate and scale)

1. Nitro reduction to 6-aminopyridine-2-carboxamide

• Catalytic hydrogenation: 5–10 wt% Pd/C (2–5 mol % Pd), H2 (1–5 bar), EtOH or MeOH, rt to 40 °C, 2–12 h. Add acid scavenger if needed to avoid over-reduction. Work up by filtration through celite, concentrate, and crystallize from alcohol/ether.
• Iron/AcOH: Fe powder (3–5 equiv), glacial AcOH/EtOH, 60–80 °C, 2–6 h; filter off iron salts, basify, extract.

2. Amide dehydration to nitrile

• SOCl2 (2–3 equiv) with catalytic DMF (0.05–0.1 equiv), reflux (60–80 °C), 2–6 h; quench cautiously onto ice/NaHCO3, extract; or POCl3 under similar conditions. Greener option: T3P (50 wt% in EtOAc) with DIPEA in 2-MeTHF or EtOAc, 50–80 °C.

3. Amide hydrolysis to acid

• Basic: 2–4 M NaOH in H2O/EtOH (1:1), reflux 2–8 h; acidify to pH ~2 to precipitate the acid.
• Acidic: 6 M HCl, 80–100 °C, 4–16 h (glass-compatible setup), then neutralize and isolate.

4. Directed metalation/electrophile trapping

• s-BuLi/TMEDA or LDA at −78 to −40 °C in THF; quench with electrophiles (CO2, aldehydes, halides). Sensitivity to over-lithiation and nitration state requires careful titration and cryogenic control.

Yields

• Literature ranges: reductions often 70–95%; dehydrations 60–90%; hydrolyses typically high (70–95%) depending on workup and substituent tolerance.

Notes

• Monitor by LC–MS or HPLC; the heteroaromatic core may show strong UV at 254 nm. Ensure adequate degassing and drying of solvents for base- or metal-mediated steps.

Safety and Handling

Item-specific (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.
• Storage: Room temperature.
• Research use: For research use only.

General safety guidance for nitro-heteroaromatics and amides (literature; not product-specific)

• Hazards: Nitroaromatics can cause irritation to skin/eyes/respiratory tract; some nitro compounds may cause methemoglobinemia upon significant exposure. Amide functionality is generally of low volatility.
• PPE: Use lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Handle powders in a fume hood to avoid dust inhalation.
• Incompatibilities: Strong reducing agents (risk of exothermic reduction of –NO2), strong oxidizers (general incompatibility), and strong acids/bases under heating (hydrolysis/condensation).
• Thermal considerations: Avoid excessive heating that could decompose the nitro group.
• First aid (summary; defer to SDS):
  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: rinse with water for several minutes; remove contaminated clothing; seek medical attention if irritation persists.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.

Always consult the product’s SDS for authoritative, lot-specific hazard and response information.

Solvent Selection

Applicability

• This product is a polar, heteroaromatic primary amide solid. Solvent selection is relevant for dissolution and for its use in synthesis/derivatization.

General solubility profile (literature; not product specification)

• High solubility: DMSO, DMF, NMP, DMAc.
• Moderate solubility: methanol, ethanol, isopropanol (often improved with warming or sonication).
• Low solubility: nonpolar solvents (hexanes, toluene) unless strong hydrogen-bonding co-solvents are used.
• Aqueous media: typically low at neutral pH; limited enhancement under acidic conditions (protonation of ring N) or basic conditions (amide remains unionized; salts can assist if functionalized).

Selection tips

• For bioassays or screening stocks: prepare concentrated solutions in dry DMSO (e.g., 10–50 mM), then dilute into assay buffers with vigorous mixing to avoid precipitation.
• For coupling, reductions, or dehydrations: choose polar aprotic media (DMF/DMAc/NMP), or greener alternatives like Cyrene or propylene carbonate when compatible with reagents.
• For recrystallization: consider alcohols (EtOH/iPrOH) or mixed solvent systems with a polar/nonpolar pair to tune solubility.

Comparison snapshot (general)

• DMSO: excellent solvency; high boiling; mixes with water; may interfere in some reactions.
• DMF/NMP: strong solvency; good for amidations and reductions; regulatory concerns (reprotox classification) — consider greener substitutes.
• Ethanol/2-PrOH: greener, but solubility may be limited at room temperature.

Storage and Reconstitution

Item-specific (from Product Data)

• Storage conditions: Room temperature.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

General guidance (not product-specific)

• Keep container tightly closed in a dry, well-ventilated place. Protect from excessive heat and direct sunlight. Store in the original container with desiccant if hygroscopicity is observed.
• Reconstitution/stock solutions: For biological screening, dissolve in anhydrous DMSO to prepare concentrated stocks (e.g., 10–50 mM). For synthetic operations, dissolve in a suitable polar aprotic solvent (DMF, DMAc, NMP, or greener alternatives) just prior to use.
• Freeze–thaw: If freezer storage of solutions is required, aliquot to avoid repeated freeze–thaw cycles. DMSO solutions are commonly stored at −20 °C; check for precipitation upon thawing and warm gently if needed.
• Stability: Nitro-heteroaromatic amides are generally stable solids under ambient conditions. For definitive shelf-life and stability, consult the CoA and SDS for this lot.

Structure and Identity

Item-specific (from Product Data)

• Product name: 6-Nitropyridine-2-carboxamide (SKU: N1008317)
• CAS: 60278-80-0
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Storage conditions: Room temperature

Literature/derived description (for orientation; not item specification)

• Molecular formula (structural deduction): C6H5N3O3
• Approximate molecular weight (computed from formula): ~167.12 g/mol
• Core scaffold: a substituted pyridine (azabenzene) ring.
• Functional groups: ring nitrogen (pyridine), an amide at C-2 (–C(=O)NH2), and a nitro group at C-6 (–NO2).
• 2D structure (verbal): a six-membered aromatic ring containing one ring nitrogen (position 1). The carbon ortho to the ring nitrogen at position 2 bears a primary carboxamide substituent; the carbon ortho on the opposite side at position 6 bears a nitro substituent. No stereocenters present; planar conjugated system across ring, amide, and nitro.

Notes

• Identifiers (SMILES/InChI) are not provided in the Product Data; consult the CoA/Spec Sheet for definitive identifiers used for this lot.

Synthetic Utility

Key functional elements

• Electron-poor heteroaromatic core (pyridine), a strongly withdrawing nitro group (–NO2) at C-6, and a primary amide at C-2.

Strategic value (literature; not product-specific)

• Bifunctional platform: independent tuning at C-6 (via nitro → amine → diazonium chemistry) and at C-2 (via amide interconversions: hydrolysis → acid, dehydration → nitrile, or coupling from the acid stage).
• Polarity handles: amide enables crystallinity/purification and confers H-bonding; nitro modulates electronics and can be leveraged for late-stage reductions.
• Directing effects: ring N and nitro can direct deprotonation or electrophilic substitution at defined positions under strong base/metalation protocols.

Typical transformations

• Nitro → amine: H2/Pd-C (1–5 mol %) in EtOH/EtOAc or MeOH under 1–5 bar H2; or Fe/AcOH; then acylation/sulfonylation to diversify.
• Amide → nitrile: SOCl2 or POCl3 (1.5–3.0 equiv) with catalytic DMF, 0–80 °C; or T3P/base in greener solvents.
• Amide → acid: refluxing aqueous base (NaOH/KOH) or HCl; re-activate as acid chloride (oxalyl chloride) for further coupling.
• Diazotization routes from the reduced aniline at C-6 enable Sandmeyer-type substitutions (C–Cl, C–CN, C–S, etc.).

Use cases

• Assembly of chelating ligands (picolinamide derivatives), heteroaryl linkers, and fragments for SAR exploration.

Target Specificity

Not applicable. This product is a small-molecule building block and not a biological targeting agent (e.g., antibody, enzyme, or ligand with defined target specificity). No antigen/epitope, species reactivity, clone, or isotype information applies.