This compound belongs to the class of organic compounds known as pyrazinecarboxamides. These are compounds containing a pyrazine ring which bears a carboxamide.
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.
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Application Protocols
No tested bioassay or analytical application protocols are provided for this item. For general handling:
Preparation of stock solutions (general): Dissolve in dry DMSO or DMF to 10–100 mM; filter (0.22 µm PTFE) if particulates remain. Store aliquots under inert gas to limit moisture uptake.
Crystallization/co-crystal screening: Prepare equimolar mixtures with co-formers (0.05–0.2 M each) in methanol/ethanol or acetonitrile; allow slow evaporation or conduct vapor diffusion.
Reaction setup: For dehydration/hydrolysis, use dry glassware, control temperature ramps, and monitor by LC–MS/HPLC.
Item-specific validated protocols and recommended dilutions: Not specified for this item; refer to CoA/Spec Sheet and SDS for any additional guidance.
Biological Roles
This product is offered strictly for research use; no clinical or diagnostic claims are made.
General biochemical context (not item-specific):
Pyrazine derivatives are common in bioactive small-molecule libraries due to their electron-deficient aromatic character and ability to engage in π–π stacking and anion–π interactions.
The diamide functionality provides dual H-bond donors/acceptors, enabling specific binding patterns in protein–ligand environments and in nucleic acid groove interactions during biophysical screening studies; however, binding profiles are highly scaffold- and substituent-dependent.
Physicochemical properties expected for a diamidopyrazine (low lipophilicity, high polarity) often translate to reduced passive permeability and increased aqueous compatibility, which can be advantageous for enzyme assays and fragment-like screening in polar buffers when solubility permits.
Metabolic/chemical stability: Primary amides are generally stable to many metabolic oxidations but can undergo amidase-catalyzed hydrolysis in biological systems (literature, context-dependent). For in vitro assays, use freshly prepared solutions and confirm absence of aggregation/precipitation by light scattering if working near solubility limits.
If biological testing is intended, evaluate cytotoxicity, solubility, and assay interference using standard panels (e.g., redox activity, fluorescence interference). Item-specific ADME or bioactivity data: Not specified for this item.
Buffer Applications
This compound is not a buffering reagent and does not constitute a conventional acid/base buffer system. It lacks a suitable conjugate acid/base pair in the physiological pH range with sufficient capacity.
Practical guidance:
If used in aqueous assays, dissolve first in a compatible co-solvent (e.g., DMSO) and then dilute into the target buffer (PBS, HEPES, or acetate), ensuring final co-solvent content remains within assay tolerance (commonly ≤1–2% v/v).
For improved apparent solubility, gentle warming and pH adjustment (slightly acidic to protonate ring nitrogens) may help, but avoid strong base unless hydrolysis is intended.
For buffer formulation details (pH ranges, recipes), select established systems such as:
Acetate (pH 3.6–5.6), MES (pH 5.5–6.7), HEPES (pH 6.8–8.2), or phosphate (pH 5.8–8.0).
Item-specific buffer specifications: Not applicable/not specified for this item.
Green Alternatives
Sustainability considerations focus primarily on solvent choice and dehydration/hydrolysis reagents, since the substrate is a stable solid.
Prefer greener solvents where feasible:
Replace DMF/NMP with Cyrene, NEP, or propylene carbonate for dissolution/reactions when compatibility allows.
Use water/ethanol mixtures and surfactant-enabled media (e.g., micellar catalysis) for hydrolysis or coupling workflows, recognizing solubility constraints of the diamide.
Reagent selection for amide-to-nitrile dehydration (general literature):
Conventional: SOCl2, POCl3, P2O5 often effective but generate corrosive waste.
Greener options: T3P (propylphosphonic anhydride) or CDI-based protocols under solvent-minimized conditions can reduce hazard profile; Burgess reagent or cyanuric chloride under controlled conditions may offer milder alternatives.
Workup/waste:
Implement aqueous base neutralization and phase-splitting to minimize chlorinated waste.
Consider solvent recovery for high-boiling dipolar aprotics via vacuum distillation when practical.
Comparison snapshot (general):
DMF vs Cyrene:
DMF: Excellent solvating power; reproductive toxin classification in some jurisdictions.
Cyrene: Bio-based dipolar aprotic with comparable polarity; higher viscosity and sometimes lower solubility for highly crystalline solids—trial recommended.
T3P: Lower volatility, easier handling, less corrosive workups; may require elevated temperature and an auxiliary base.
Pharmaceutical Uses
No pharmacopeial status or excipient grade is specified for this item; refer to CoA/Spec Sheet. This product is for research use only.
General formulation/manufacturing context (non-clinical, non-therapeutic):
As a heteroaromatic diamide, 2,5-pyrazinedicarboxamide may be used as a synthetic intermediate or reference standard in medicinal chemistry programs exploring azine scaffolds.
The strong H-bonding capacity and electron-deficient ring can be leveraged to modulate solubility and binding vectors in PROTAC linkers, fragment libraries, or as a polar end-cap in conjugates.
Solid-state behavior (likely high melting, H-bonded crystal lattice) suggests attention to polymorphism and hydrate formation during solid-form screening, if pursued for pre-formulation research.
For analytical development, typical controls include HPLC purity, residual solvents, and identity confirmation by LC–MS and NMR; UV response should be verified due to azine chromophore presence (exact UV data: Not specified for this item).
Any claims of therapeutic application, dosing, or clinical use are outside scope and are not made here.
Physical Properties
Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.
General/literature and qualitative properties (for guidance only):
Aggregated polarity: High, due to two primary amides and a diazine ring; strong H-bond donor/acceptor capacity.
Physical state: Typically an off-white to pale solid (literature expectation for diamides), often crystalline.
Solubility (qualitative, literature):
Water: Low to moderate at ambient temperature; solubility may increase with gentle heating due to strong crystal lattice via H-bonding.
Polar aprotic: Good solubility in DMSO and DMF; moderate in NMP; limited in acetonitrile.
Protic: Often dispersible in hot methanol/ethanol; limited in isopropanol.
Nonpolar: Poor in ethers, toluene, hydrocarbons.
Ionization: Amide N–H is non-basic/weakly acidic; pyrazine ring nitrogens are weak bases (pKaH typically ~0–1 for pyrazines, literature), so salt formation under strongly acidic conditions is possible, but the neutral diamide predominates at neutral pH.
Partitioning: Expected low logP/ClogP due to bis-amide functionality (literature qualitative assessment).
Thermal behavior: Primary diamides often exhibit elevated melting points due to robust H-bond networks; handle with appropriate heating if recrystallization is pursued. Specific MP/BP: Not specified for this item; refer to CoA/Spec Sheet.
Spectroscopic notes (general): Strong IR C=O stretches (~1640–1690 cm−1, literature) and characteristic pyrazine ring modes; UV absorbance in the near-UV due to the azine ring (exact UV cutoff/ε: Not specified for this item).
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/additives: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and guidance:
Without a declared grade, end-users should verify suitability by reviewing the Certificate of Analysis (CoA) for assay, residual solvents, water content (Karl Fischer), and chromatographic purity. If using for structure–property or supramolecular studies, also check polymorph information where available.
Typical grade definitions (general):
Research/Chemical grade: Suitable for general synthesis and screening.
≥98–99% (assay) organic building block: Appropriate for medicinal chemistry and materials R&D; check HPLC/GC profiles and metals.
HPLC grade (for solvents/UV-critical reagents): Defined by low UV background and low particulate; not usually applicable to solid building blocks like this compound.
UV specifications, trace metals, and other micro-specs: Not specified for this item; refer to CoA/Spec Sheet.
Practical tips:
For chromatographic or crystal engineering work, request lot-specific HPLC area % and water content.
If using in metal coordination or MOF synthesis, assess trace metal background; if necessary, pre-treat via recrystallization to reduce adventitious ions.
Confirm identity by NMR/HRMS/IR against literature references; diamide NH signals can be temperature- and solvent-dependent (H-bonding/tautomerism).
Reaction and Applications
Use-cases focus on the diamide functionality embedded in an electron-deficient azine ring, enabling several synthetic and materials-oriented applications.
Transformations of the primary amides (general literature guidance):
Dehydration to dinitrile: Primary amides can be dehydrated to the corresponding nitriles using SOCl2, POCl3, T3P/oxalyl chloride, or cyanuric chloride under controlled conditions. For the 2,5-pyrazine scaffold, this yields 2,5-pyrazinedicarbonitrile, a versatile intermediate.
Hydrolysis to diacid: Under strong aqueous acid or base and heat, the amides can be hydrolyzed to 2,5-pyrazinedicarboxylic acid, which may be further activated to acid chlorides/esters.
Coupling/derivatization at the amide nitrogen: Formation of N-acyl ureas or imidates (via activation) enables elaboration of hydrogen-bonding networks for supramolecular chemistry.
Heteroaromatic context:
The pyrazine ring is electron-poor, which can modulate the rate of transformations adjacent to the ring and favor coordination to Lewis acids/transition metals via ring nitrogens.
Materials and supramolecular applications:
The bis-amide motif forms predictable R2 2(8) H-bond synthons, useful for crystal engineering and co-crystal screening.
Potential as an organic linker/ligand in coordination polymers/MOFs through ring N and carbonyl O interactions (literature precedents for related diamidopyrazines).
Practical tips:
Ensure rigorous drying of polar aprotic solvents (DMF, DMSO) for moisture-sensitive steps (e.g., dehydration).
For hydrolysis, consider phase behavior: limited water solubility can be mitigated by mixed aqueous/organic media or by converting first to more soluble salts under acidic conditions.
Monitor reactions by LC–MS/HPLC; amide to nitrile conversion is readily tracked by mass shift (−18 Da per amide).
Reaction Conditions
General literature guidance for representative transformations; optimize per your lab’s conditions.
Amide dehydration to dinitrile
Typical reagents: SOCl2 (2–6 equiv) or POCl3 (2–4 equiv) with catalytic DMF; or T3P (50% in EtOAc) with base (NEt3, DIPEA).
Solvent: Anhydrous dichloromethane, toluene, or DMF (for SOCl2/POCl3 routes); EtOAc or acetonitrile for T3P.
Temperature/time: 60–110 °C, 2–16 h depending on reagent and scale.
Workup: Quench cautiously into ice-cold aqueous base; extract organics; neutralize acidic residues. Monitor by LC–MS (−18 Da per amide).
Hydrolysis to diacid
Conditions: Refluxing 6 M HCl or 2–4 M NaOH (aqueous), 80–110 °C, 4–24 h; then acidify to precipitate diacid.
Co-solvent: Dioxane or ethanol may aid wetting; avoid if unnecessary to improve green metrics.
Amidation from diacid/diester (to access the diamide scaffold)
Activation: Convert diacid to diacyl chloride (SOCl2, catalytic DMF), then react with NH3 in THF/Et2O at 0–25 °C; or use CDI/EDCI coupling with NH4HCO3/NH3 in DMF.
Purification: Recrystallization from hot alcohols or RP-HPLC.
Supramolecular assembly/co-crystal screening
Solvents: Methanol, ethanol, acetonitrile, acetone, DMSO; slow evaporation or vapor diffusion against antisolvents (Et2O, hexanes).
Additives: Co-formers with complementary H-bonding (e.g., dicarboxylic acids, pyridyl donors). Screen temperatures 5–40 °C.
All numeric parameters above are typical literature ranges, not product specifications.
Safety and Handling
Item-specific hazard data: Not specified for this item; refer to the SDS for definitive classification and protective measures.
General safety guidance for heteroaromatic diamides (informational only):
GHS classification and pictograms: Not specified for this item; consult SDS.
Potential hazards: Low volatility solid; dust may cause mechanical irritation to eyes/respiratory tract. Primary amides are generally of low acute hazard but can cause skin/eye irritation upon contact. Avoid inhalation of dust and prolonged skin exposure.
Peroxide formation: Not applicable (no ether functionality).
PPE: Use lab coat, safety glasses or goggles, and appropriate chemically resistant gloves (e.g., nitrile). Employ dust control (weighing in a fume hood) and avoid generating aerosols.
Handling: Hygroscopicity is typically low-to-moderate for diamides, but moisture can influence solid-state form and weigh accuracy. Keep container tightly closed under inert gas as provided (argon blanket) to preserve material quality.
Incompatibilities: Strong dehydrating or chlorinating agents may convert amides to nitriles/acid chlorides; strong oxidizers should be avoided unless intended for synthesis. Thermal decomposition can occur on strong heating.
First aid (overview; see SDS for details):
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin contact: Wash with soap and water; remove contaminated clothing.
Eye contact: Rinse cautiously with water for several minutes; remove contact lenses if present and easy.
Ingestion: Rinse mouth; seek medical advice. Do not induce vomiting unless directed.
Fire: Use CO2, dry chemical, or foam. Combustion may produce NOx/CO/CO2.
Solvent Selection
Solubility/miscibility profile (general guidance for diamidopyrazines):
Polar aprotic: DMSO and DMF are preferred solvents for stock solutions and reactions involving this substrate due to strong H-bond accepting character and ability to disrupt lattice energy.
Protic solvents: Hot methanol or ethanol can dissolve moderate amounts; consider gentle heating (40–60 °C) and stirring/sonication.
Aqueous systems: Limited solubility at neutral pH; solubility can increase modestly in acidic media (protonation of ring nitrogens) but amide remains largely unionized. Avoid strong base unless hydrolysis is intended.
Nonpolar/medium polarity: Poor solubility in ethyl acetate, THF, toluene, and alkanes.
Polarity context:
The molecule is highly polar (two primary amides; diazine ring). Expect strong intermolecular H-bonding and low volatility.
When to choose this compound vs alternatives:
Select 2,5-pyrazinedicarboxamide when robust H-bond donor/acceptor motifs are desired (e.g., crystal engineering, co-crystals) or when a diamide handle on a pyrazine core is required for subsequent transformations (e.g., dehydration to dinitriles, hydrolysis to diacids).
Small comparison (general):
2,5-Pyrazinedicarboxamide vs 2,5-pyrazinedicarboxylic acid: The amide is less acidic, more thermally robust, and typically less water-soluble but more compatible with polar aprotic media.
2,5-Pyrazinedicarbonitrile: The nitrile is less polar, more soluble in organics, but less H-bond active and less reactive toward hydrolysis than the amide.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
General storage guidance for solid diamides:
Keep tightly closed in original container under an inert atmosphere (argon) to maintain dryness and mitigate atmospheric moisture uptake that can affect weigh accuracy and crystal form.
Store away from strong oxidizers and dehydrating/chlorinating agents. Protect from prolonged exposure to light and heat.
Reconstitution/preparation of solutions (general guidance):
Solvents: DMSO or DMF recommended for concentrated stocks; hot ethanol/methanol for less concentrated solutions. Water solubility is limited at neutral pH; consider co-solvent strategies.
Concentration: Common lab stocks 10–100 mM in DMSO; filter-sterilize if needed (0.22 µm PTFE) and aliquot to avoid repeated opening.
Stability of solutions: Solutions in DMSO/DMF are typically stable for weeks at 2–8 °C under inert gas and desiccation; prepare fresh if discoloration/precipitation occurs.
Freeze–thaw: For solutions, minimize cycles by aliquoting; solids generally tolerate ambient storage as specified.
Any item-specific reconstitution procedures, stabilizers, or shelf-life: Not specified for this item; refer to CoA/Spec Sheet.
Structure and Identity
Brief overview: 2,5-Pyrazinedicarboxamide is a diamide-substituted pyrazine (an azine heteroaromatic) with strong hydrogen-bond donor/acceptor capability.
Item-specific (from Product Data):
SKU: P728056
Product Name: 2,5-Pyrazinedicarboxamide
CAS: 41110-27-4
InChIKey: 47297
Storage: Room temperature, Argon charged
Shipped In: Normal
Research Use: For research use only
Literature/computed identifiers (for reference; not item specifications):
Molecular formula (literature rationale): C6H6N4O2 (pyrazine core C4H4N2 with two –CONH2 substituents)
Molecular weight (calculated from formula): ~166.14 g/mol
Core ring: Pyrazine (1,4-diazine), a six-membered aromatic ring with two ring nitrogens para to each other.
Substitution pattern: Carboxamide groups at the 2- and 5-positions of the ring (diamidation across the ring nitrogens).
Functional groups: Two primary amides (–CONH2 ×2); heteroaromatic diazine ring (two ring nitrogens).
H-bonding: 2 H-bond donors (amide NHs) and 4+ H-bond acceptors (2 amide C=O, 2 ring N), favoring supramolecular assembly and metal coordination via lone pairs on ring N and amide carbonyls.
2D description: An aromatic hexagon bearing two opposite ring nitrogens (positions 1 and 4). At carbons 2 and 5, each carries a –C(=O)–NH2 substituent projecting roughly coplanar with the ring, enabling conjugation between the amide carbonyl and the azine π-system.
Synthetic Utility
Key reactive elements and strategies (general literature guidance):
Functional groups: Two primary amides and a pyrazine ring (diazine). The amides are handles for interconversion chemistry; the ring nitrogens provide coordination sites and electronic control.
Interconversions:
Amide → Nitrile: Dehydration to 2,5-pyrazinedicarbonitrile (valuable for subsequent reductions to diamines or for cross-coupling after further derivatization).
Amide → Acid/Acid chloride/Ester: Hydrolysis to diacid, then activation (e.g., SOCl2, oxalyl chloride) to diacyl chloride for esterification or amide re-coupling.
N-derivatization: Formation of N-acyl ureas, imides, or imidates to build extended H-bonding networks for supramolecular assemblies.
Electronic effects: The electron-poor pyrazine ring reduces nucleophilicity at adjacent positions and can stabilize certain intermediates; ring nitrogens can modestly direct metalation or coordinate to catalysts/metal ions in assembly chemistry.
Retrosynthetic value: A convergent approach via 2,5-pyrazinedicarboxylic acid/ester intermediates allows late-stage conversion to the diamide under standard amidation conditions (e.g., EDCI/HOBt, CDI, or acid chloride routes), enabling parallel synthesis of analogs.
Purification/analysis: Expect limited mobility on silica gel due to strong H-bonding; reverse-phase HPLC or recrystallization from polar solvents is often effective. IR (amide C=O), 1H/13C NMR (amide NH exchange, downfield shifts), and LC–MS (M+H+ ~167, literature) are diagnostic.
Target Specificity
Not applicable. This product is a small-molecule chemical, not a biological targeting reagent (e.g., antibody, ligand with defined protein specificity). No item-specific target data are provided.
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