Pyrazine-2,5-diol - ≥95% , CAS No.134434-28-9

CAS: 134434-28-9 Cat. No.: P1034262 Formula: C₄H₄N₂O₂ Peso molecolare: 112.090

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifiche e purezza

≥95%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥95%

Nomi e identificatori

• Sorrisi canonici: C1=C(N=CC(=O)N1)O
• IUPAC Name: 5-hydroxy-1H-pyrazin-2-one
• InChIKey: USHRADXTTYICIJ-UHFFFAOYSA-N
• INCHI: 1S/C4H4N2O2/c7-3-1-5-4(8)2-6-3/h1-2H,(H,5,8)(H,6,7)
• Peso molecolare: 112.090

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Classe Diazines
      • Subclass Pyrazines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Classe: Diazines
• Subclass: Pyrazines
• Intermediate Tree Nodes: Not available
• Direct Parent: Pyrazines
• Alternative Parents: Heteroaromatic compounds Lactams Azacyclic compounds Organooxygen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Pyrazine - Heteroaromatic compound - Lactam - Azacycle - Organic nitrogen compound - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Aromatic heteromonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as pyrazines. These are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms.
• 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

Proprietà chimiche e fisiche

• Peso molecolare: 112.090 g/mol
• XLogP3: -0.900
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 112.027 Da
• Monoisotopic Mass: 112.027 Da
• Topological Polar Surface Area: 61.700 Ų
• Heavy Atom Count: 8
• Formal Charge: 0
• Complexity: 171.000
• 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 application protocols are provided in the Product Data for this item.

• General laboratory use examples (non-validated)
  • Stock solution preparation: Dissolve in DMSO to 10–100 mM; filter (0.22 µm) if needed; store aliquots to minimize freeze–thaw. Verify solubility and stability before use.
  • O-alkylation screen: Combine substrate (1.0 equiv), K2CO3 (2.5 equiv), alkyl bromide (1.2 equiv) in dry DMF (0.1 M); stir 50 °C, monitor by LC–MS; work up and purify.

For validated, application-specific protocols, consult primary literature or develop method parameters tailored to your system. Always confirm compatibility and safety with a small-scale trial.

Biological Roles

• Item-specific biological role (Product Data): Not specified; this product is supplied for research use only.
• General context (no clinical claims)
  • Pyrazine derivatives occur widely in natural products, flavors, and bioactive scaffolds. A 2,5-dihydroxylated pyrazine presents multiple hydrogen-bonding vectors and can act as a chelating, polar fragment in biochemical probe design.
  • The electron-deficient diazine core can influence binding via π-stacking and cation–π or anion–π interactions, while the diol motif may engage in bidentate H-bonds with protein residues or nucleic acids (conceptual, target-dependent).
  • In buffered aqueous media, stepwise deprotonation of the OH groups will modulate charge state and solubility, impacting biomolecular interactions and permeability.
• Use in life-science research (general)
  • As a polar fragment for SAR exploration in enzyme or receptor ligand series.
  • As a metal-binding handle in metalloenzyme probe development or as a reporter in coordination-based sensing.

Note: No endogenous metabolic role or specific pathway association is assigned here. Verify compatibility with biological assays (vehicle, pH, ionic strength) and avoid inferring therapeutic properties.

Buffer Applications

This compound is not a conventional buffering agent and does not define a standard buffer system.

• Practical notes (general)
  • Solubility in water increases upon deprotonation with mild base (e.g., NaHCO3/Na2CO3). If inclusion in aqueous assays is desired, prepare a concentrated stock in DMSO or basified water, then dilute into the final buffer while monitoring pH.
  • Avoid strong acids/bases that might induce degradation or unwanted tautomerization; confirm stability by analytical HPLC in the specific buffer matrix.

For routine buffering needs, use established systems (e.g., phosphate, HEPES, Tris) and introduce this compound as a solute/additive only if chemically compatible.

Green Alternatives

This product is a heteroaromatic building block rather than a solvent. “Green alternatives” therefore pertain to choosing more sustainable media and reagents when using it.

• Greener solvent choices for common transformations (general guidance)
  • O-Alkylation: Replace DMF/DMSO where possible with 2-methyltetrahydrofuran (2-MeTHF), propylene carbonate, or aqueous ethanol with phase-transfer catalysis—subject to solubility and base compatibility.
  • O-Acylation: Use ethyl acetate or 2-MeTHF with organic bases (Et3N) and catalytic DMAP rather than chlorinated solvents; or perform in acetonitrile with minimized volume.
  • Purifications: Favor ethanol/ethyl acetate/hexanes over chlorinated eluents; explore crystallization to avoid chromatography.

Small comparison (general expectations)

• DMF/DMSO
  • Pros: Excellent solubility, high yields.
  • Cons: EHS concerns, difficult removal.
• 2-MeTHF/EtOAc/MeCN
  • Pros: Lower environmental impact, easier workup.
  • Cons: Solubility may be limiting; may require higher temperature or longer time.

Process intensification options

• Microwaves or flow reactors can shorten reaction times and reduce solvent volumes.
• Aqueous-base conditions (carbonate) with a green co-solvent may enable O-alkylation under milder, safer conditions.

Pharmaceutical Uses

• Item-specific regulatory status (Product Data): Not specified for this item; supplied for research use only.
• General formulation/CMC context (no clinical claims)
  • As a highly polar heteroaromatic diol, pyrazine-2,5-diol could serve as a synthetic intermediate toward drug-like analogs rather than as an excipient. Its hydrogen-bonding and metal-binding properties are of interest in medicinal chemistry scaffold design.
  • Salt formation: While phenolic OH groups are weakly acidic, deprotonated forms (phenolates) are transient and not typically isolated as pharmaceutically acceptable salts; derivatives (ethers/esters) are more common in APIs.
  • Analytical methods: HPLC with aqueous-organic mobile phases (water/MeOH or water/ACN with acid modifiers) and LC–MS detection are suitable for assay and impurity profiling; use stability-indicating methods to monitor potential oxidation.

No pharmacopeial monographs or excipient roles are asserted here. All uses are restricted to laboratory research and development.

Physical Properties

• Appearance (Product Data): Not specified for this item; refer to CoA/Spec Sheet.
• Grade/Purity (Product Data): Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight (literature/computed): ~112.09 g/mol (C4H4N2O2).
• Physical state (general chemistry expectation): Typically an aromatic diol is a crystalline solid due to H-bonding; confirm with CoA/SDS for this item.
• Melting point, boiling point, density, refractive index: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (general chemistry guidance)
  • Polar protic/aprotic: Expected good solubility in water at elevated pH (deprotonated forms), lower in neutral water; soluble in polar organics (DMSO, DMF, alcohols). Verify experimentally.
  • Nonpolar solvents: Poor solubility expected in alkanes/ethers due to polarity and H-bonding.
• Acid–base properties (literature/general): Phenolic OH groups on an electron-deficient pyrazine ring are more acidic than phenol; stepwise deprotonation can occur in basic media. Specific pKa values are not provided here.
• Partitioning (general): Expected low logP and high polarity; favorable for polar-phase and H-bonding interactions.
• Hygroscopicity: Not specified for this item; refer to CoA/Spec Sheet.

Note: For authoritative specifications and batch-specific data (mp, water content, residual solvents, UV cutoff), consult the CoA/Spec Sheet for this SKU.

Quality and Grades

• Item-specific quality (Product Data)
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• What grade implies (general guidance)
  • Research grade materials are suitable for synthetic and analytical lab use. If an “HPLC,” “LC-MS,” or “BioUltra” style grade is offered for this compound in other contexts, those grades typically indicate tighter limits on nonvolatile residue, UV absorbance profile, and trace metal content—none of which are specified for this item.
• Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
• QC considerations for pyrazine-2,5-diol (general best practices)
  • Identity confirmation: 1H/13C NMR in DMSO-d6 or D2O (with base), HRMS, and IR (broad O–H, ring C=N stretches). Elemental analysis can support formula confirmation.
  • Purity profiling: HPLC/UPLC in aqueous-organic gradients (e.g., water/MeOH with formic acid) and melting behavior if crystalline.
  • Residual solvents/water: Karl Fischer for water; GC for volatiles if required. Specific limits are not provided for this item.

For lot-specific analytical data, consult the Certificate of Analysis (CoA) and Spec Sheet.

Reaction and Applications

• Functional group leverage (general chemistry)
  • Two phenolic OH groups on an electron-deficient pyrazine enable selective O-functionalization (etherification, esterification) and potential chelation when deprotonated.
  • The pyrazine ring is a π-deficient heteroarene, favoring nucleophilic aromatic substitution only when suitably activated at specific positions; direct electrophilic substitution is typically disfavored.
• Representative applications (literature/general)
  • O-Alkylation: Alkyl halides or sulfonates with K2CO3/Na2CO3, Cs2CO3, or NaH in DMF/DMSO/MeCN to give mono- or di-ethers; temperature 20–80 °C.
  • O-Acylation: Acyl chlorides or anhydrides with base (pyridine, triethylamine) and catalytic DMAP in dichloromethane or acetonitrile to furnish esters.
  • Oxidation/tautomer management: Under oxidative conditions, diol-like forms may interconvert or oxidize toward diketone-like pyrazine-2,5-dione; control redox environment accordingly.
  • Metal complexation: The 2,5-dioxy motif (in diolate form) can chelate metals (e.g., Cu, Ni, Fe) for coordination studies or as ligand scaffolds.
• Materials / medicinal chemistry roles (general)
  • H-bond donor/acceptor rich scaffold for fragment-based design; ring nitrogens can modulate pKa and solubility.
  • Precursor to substituted pyrazines via O-protection → cross-coupling or ring functionalization strategies.
• Practical tips
  • Dry the substrate and solvents for base-mediated O-functionalizations; water competes for base and lowers yields.
  • Control stoichiometry to favor mono- vs di-substitution; protect or transiently block one OH for orthogonal elaboration.
  • Monitor by LC-MS/HPLC as polarity shifts markedly on O-derivatization.

Reaction Conditions

General guidance only; adapt to your substrate scope and safety protocols.

• O-Alkylation (Williamson-type)
  • Base: K2CO3 (2.0–3.0 equiv) or Cs2CO3; for more challenging electrophiles, NaH (60% oil) 1.2–2.0 equiv.
  • Solvent: Dry DMF, DMSO, or MeCN (0.05–0.2 M).
  • Temperature/time: 25–80 °C, 2–16 h. Monitor by TLC/HPLC. Typical literature yields for related systems: 50–90% depending on sterics/leaving group.
• O-Acylation
  • Reagents: Acyl chloride (1.1–2.0 equiv) or anhydride; base Et3N or pyridine (2–3 equiv); catalytic DMAP (5–10 mol%).
  • Solvent: CH2Cl2, MeCN, or EtOAc; 0–25 °C to control exotherm.
  • Notes: Sequential acylation allows diesters; quench with aqueous bicarbonate.
• Deprotection of benzyl ethers (if used)
  • Hydrogenolysis: H2 (1–3 bar), Pd/C (5–10 wt%), MeOH/EtOH, rt–40 °C.
• Metal complexation studies
  • Generate diolate with mild base (e.g., NaOMe in MeOH or Na2CO3 in H2O/EtOH), then add metal salt (e.g., Cu(OAc)2) at 0–25 °C; characterize by UV–vis/ESI-MS.
• Workup/purification
  • Aqueous quench, extract with EtOAc/MTBE; wash with brine. Purify by silica gel using polar eluents (EtOAc/MeOH/CH2Cl2) or by crystallization from alcohols when feasible.

These conditions are representative for phenolic pyrazines; optimize for your specific electrophile and selectivity goals.

Safety and Handling

• GHS/CLP classification (Product Data): Not specified; consult the SDS for definitive hazard and precautionary statements.
• Signal word / H-statements / pictograms: Not specified for this item; refer to SDS.
• General hazards (general chemistry knowledge)
  • Low volatility heteroaromatic diols typically present low acute inhalation risk; main exposure routes are skin/eye contact and ingestion.
  • Phenolic-type compounds may cause eye/skin irritation; handle to minimize contact.
• Recommended PPE and controls
  • Wear lab coat, safety glasses or face shield, and appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood when weighing/transfer to control dust.
• Handling tips
  • Avoid generating dust and aerosol. Keep containers tightly closed to limit moisture uptake and contamination.
  • If using strong bases for deprotonation/derivatization, manage exotherms and add base slowly.
• Incompatibilities (general): Strong oxidizers, strong bases/acylating agents without proper control; reactive acyl/alkyl halides can exothermically O-acylate/O-alkylate.
• First aid overview (refer to SDS for details)
  • Skin: Wash with soap and water; remove contaminated clothing.
  • Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present and easy to do; continue rinsing.
  • Ingestion/Inhalation: Seek medical attention; move to fresh air if inhaled.
• Fire safety
  • Likely combustible organic solid. Use CO2, dry chemical, or foam on small fires; water spray for cooling. Thermal decomposition may produce NOx and COx.

Always consult the product-specific SDS for authoritative safety guidance before use.

Solvent Selection

• Polarity profile (general)
  • A polar, H-bonding solid; dissolves best in high–dielectric solvents. Expect good solubility in DMSO, DMF, and formamide; moderate in alcohols; minimal in nonpolar media.
• Practical solvent choices (general guidance)
  • Stock solutions for screening/biology: DMSO is commonly used; filter sterilize if required. For aqueous work, dissolve with slight basification (e.g., NaOH) to form phenolate(s), then adjust pH if compatible with your application.
  • O-alkylation/acylation: Dry DMF, DMSO, MeCN, or acetone with carbonate or alkoxide bases. THF or 2-MeTHF can be used when solubility is adequate.
  • Metal coordination studies: Alcohol/water mixtures with controlled pH to promote chelation of the deprotonated diol.
• Comparison to alternatives (general)
  • If avoiding dipolar aprotics (DMF/DMSO), consider greener ethers (2-MeTHF) or esters (EtOAc/IPA mixtures) provided solubility and base compatibility are met.
• Notes
  • Avoid strong acids in water if ring hydrolysis/oxidation is a concern; the electron-poor pyrazine ring can be sensitive under harsh conditions.
  • Always verify solubility and stability empirically at intended concentration and pH.

Storage and Reconstitution

• Storage conditions (Product Data): Store at room temperature.
• Shipping (Product Data): Not specified for this item; refer to CoA/Spec Sheet.
• Reconstitution/solution preparation (general guidance)
  • Prepare concentrated stocks in DMSO or in aqueous base (e.g., 0.01–0.1 M NaOH) if water solubility at neutral pH is insufficient. Adjust pH after dilution as needed for your application.
  • Filter solutions through 0.22 µm PTFE/nylon filters for analytical or biological assays to remove particulates.
• Stability considerations (general)
  • Protect from prolonged exposure to strong oxidants and from extreme pH. If long-term storage of solutions is required, aliquot and store at 2–8 °C (aqueous) or ≤−20 °C (DMSO), minimizing freeze–thaw cycles. Inspect for discoloration or precipitation before use.
• Container/closure
  • Keep tightly sealed in an inert, clean, dry container. Desiccant storage may be beneficial for hygroscopic materials; confirm need for this item via CoA/SDS.

Always refer to the lot-specific CoA and SDS for definitive storage, stability, and handling guidance.

Structure and Identity

A heteroaromatic diol on a diazine ring. Pyrazine-2,5-diol (also called 2,5-dihydroxypyrazine) bears two hydroxyl groups on an electron-deficient pyrazine core, enabling rich hydrogen-bonding and chelation chemistry.

• Item identifiers (Product Data)
  • SKU: P1034262
  • CAS: 134434-28-9
  • PubChem CID: 23368901
  • InChIKey (as provided): 367951
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Identity descriptors (literature/computed)
  • Preferred name: Pyrazine-2,5-diol
  • Synonyms: 2,5-Dihydroxypyrazine (literature)
  • Molecular formula: C4H4N2O2 (literature/computed from structure)
  • Molecular weight: ~112.09 g/mol (literature/computed)
• Structural features (general chemistry description)
  • Core: 1,4-diazine (pyrazine) ring; planar, six-membered aromatic system with two ring nitrogens at positions 1 and 4.
  • Substitution: Hydroxyl groups at C-2 and C-5 (each adjacent to a ring nitrogen), arranged in a 1,4-relationship across the ring (para to each other in the pyrazine framework).
  • Functional groups: Two phenol-like OH groups (H-bond donors) on an electron-poor heteroaromatic (multiple H-bond acceptors: two ring nitrogens and two hydroxyl oxygens).
  • Tautomerism (literature): Can display keto–enol tautomerism with diketone-like forms under certain conditions, influencing acidity and coordination behavior.
  • 2D description: A flat pyrazine ring with N atoms at opposite vertices; OH substituents occupy the two carbons between the nitrogens, giving a symmetric diol.

Synthetic Utility

• Key reactivity handles (general chemistry)
  • Two phenolic OH groups allow orthogonal protection/functionalization: silyl ethers (TBS/TIPS), benzylation, alkylation (Williamson), ester formation (acyl chlorides/anhydrides).
  • The electron-deficient pyrazine ring can participate in ring transformations or serve as an acceptor in cycloaddition/electrochemical functionalization methodologies.
• Strategies enabled
  • Divergent synthesis: Mono-protect one OH to differentiate positions; elaborate the other to introduce linkers, solubilizing groups, or metal-binding motifs.
  • Ligand design: Convert to diolate or O,N-bidentate ligands for coordination chemistry and catalysis studies.
  • Oxidation state modulation: Manage conditions to access related dione or mixed O/N-protected species, enabling property tuning (e.g., lipophilicity, electronics).
• Named/related transformations (literature/general)
  • Williamson ether synthesis (O-alkylation) using alkyl halides and carbonate/alkoxide base in polar aprotic solvents.
  • Steglich or Schotten–Baumann esterifications for O-acylation.
  • Metal-mediated couplings on appropriately halogenated derivatives of the ring (if prepared), e.g., Suzuki/Miyaura on 2- or 5-substituted pyrazine congeners.
• Practical considerations
  • Use dry conditions; water competes with base and reduces O-alkylation efficiency.
  • Control temperature to avoid side reactions (over-alkylation, rearrangements); monitor by LC–MS.
  • For selective mono-functionalization, employ sub-stoichiometric electrophile or temporary protecting groups.

Target Specificity

Not an antibody, enzyme, or biologic. No target-binding specificity is provided for this small-molecule building block in the Product Data.

• Item-specific data: Not specified for this item; refer to CoA/Spec Sheet.
• General note: Any biological target engagement would be context- and derivative-dependent and must be established empirically.