Pteridin-4-ol - ≥97% , CAS No.700-47-0

CAS: 700-47-0 Cat. No.: P1073199 EC Number: 211-845-1 PubChem CID: 135460266

GRADE & PURITY ≥97%

Storage

Room temperature

Specifications

Specifications & Purity

≥97%

Storage

Room temperature

Purity

≥97%

Names and Identifiers

• Canonical Smiles: C1=CN=C2C(=N1)C(=O)NC=N2
• IUPAC Name: 3H-pteridin-4-one
• InChIKey: UWWUXWWWOUNMKW-UHFFFAOYSA-N
• INCHI: 1S/C6H4N4O/c11-6-4-5(9-3-10-6)8-2-1-7-4/h1-3H,(H,8,9,10,11)
• Isomeric SMILES: C1=CN=C2C(=N1)C(=O)NC=N2
• Alternate CAS: 700-47-0
• PubChem CID: 135460266
• NSC Number: 67308

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Pteridines and derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Pteridines and derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Pteridines and derivatives
• Alternative Parents: Pyrimidones Pyrazines Vinylogous amides Heteroaromatic compounds Azacyclic compounds Organooxygen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Pteridine - Pyrimidone - Pyrimidine - Pyrazine - Heteroaromatic compound - Vinylogous amide - Azacycle - Organic nitrogen compound - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as pteridines and derivatives. These are polycyclic aromatic compounds containing a pteridine moiety, which consists of a pyrimidine fused to a pyrazine ring to form pyrimido(4,5-b)pyrazine.
• 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

Chemical and Physical Properties

• Molecular Weight: 148.120 g/mol
• XLogP3: -0.800
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 148.039 Da
• Monoisotopic Mass: 148.039 Da
• Topological Polar Surface Area: 67.200 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 203.000
• 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 application protocols (e.g., WB, IHC, IF, FC) are applicable to this small-molecule reagent.

General handling protocols (for laboratory use)

• Prepare stock solutions in DMSO or DMF at a known concentration (e.g., 10–100 mM). Filter if necessary through 0.22 µm PTFE.
• For biochemical assays, dilute stocks into buffer just prior to use; keep final DMSO ≤1–2% unless validated otherwise.
• For synthetic use, dry solvents and control pH/tautomer as needed; monitor reactions by LC–MS or NMR.

Item-specific tested applications/dilutions: Not specified for this item.

Biological Roles

General biochemical context (not specific to this item; for background only)

• Pteridine cores are foundational to several biological cofactors and pigments, including pterins (e.g., biopterin), folates, and flavins (isoalloxazine is a tricyclic relative). These systems participate in redox catalysis and one-carbon metabolism.
• The simple pteridin-4-one/4-ol motif represents the lactam–lactim fragment seen in many pterins; tautomerism and protonation state are key to binding in enzyme active sites.
• In proteins/enzymes, binding pockets often exploit the electron-deficient ring for π–stacking and multiple hydrogen bonds to ring nitrogens and the 4-oxo/4-hydroxyl functionality (literature observations from pteridine-dependent enzymes).
• As an isolated research chemical, Pteridin-4-ol does not have a direct biological role; however, it serves as a minimalist scaffold to probe recognition elements of pteridine-binding proteins or to construct analogs for biochemical assays.

Practical considerations for biochemical work

• Solubilize in DMSO to prepare concentrated stocks; dilute into assay buffers with attention to final DMSO percentage (typically ≤1–2%).
• pH strongly influences tautomer/protonation; conduct binding or spectroscopic measurements across pH to map microstate-dependent interactions.
• Spectroscopy: pteridine chromophores show UV absorbance in the 250–350 nm region (literature for related pteridines); determine exact spectra experimentally for this compound.

Buffer Applications

This compound is not a buffering agent and is not typically used to prepare buffer systems.

Research-use notes (general)

• For biophysical assays involving Pteridin-4-ol, choose a buffer that maintains a consistent protonation state (e.g., citrate pH 3–6, phosphate pH 6–8, borate pH 8–10). The compound itself does not confer buffering capacity.
• If studying tautomerism or binding, perform pH titrations using standard buffers and track spectral/NMR changes.

Item-specific buffer specifications: Not applicable and not specified for this item; refer to your assay’s validated conditions.

Green Alternatives

Solvent and reagent choices dominate the green profile for heteroaromatic syntheses.

Greener solvent substitutions (general guidance)

• Replace chlorinated solvents (DCM) in N-oxidations with acetonitrile or ethyl acetate when compatible with oxidant and solubility.
• Use 2-methyltetrahydrofuran (2-MeTHF) or cyclopentyl methyl ether (CPME) instead of THF/MTBE for extractions and some reactions; both offer better safety/renewability profiles.
• Favor aqueous ethanol or water–acetone mixtures for crystallizations and washings where solubility permits.

Illustrative tradeoffs (literature/general)

• DMSO vs Cyrene (dihydrolevoglucosenone): Cyrene can substitute for DMF/DMSO in certain SNAr or coupling setups; however, substrate solubility and base stability must be verified.
• Peracids vs hydrogen peroxide/urea–hydrogen peroxide (UHP): H2O2-based systems reduce organic waste and halogenated byproducts, though reaction rates/selectivity may differ.

Small comparison (general)

• Parameter | DCM | Acetonitrile | 2-MeTHF
• Hazard | Volatile, chlorinated | Toxic but non-chlorinated | Flammable, lower toxicity
• Boiling point | Low (39–40 °C) | 82 °C | 80 °C
• Renewability | Fossil | Fossil | Bio-based option

Process recommendations

• Evaluate solvent selection with CHEM21/ACS GCI guides; prioritize low-toxicity, high-recovery solvents.
• Implement solvent recovery and metal scavenging after Pd-catalyzed steps to reduce waste.
• Avoid stoichiometric halogenating agents where catalytic or electrochemical alternatives exist.

Pharmaceutical Uses

Formulation/manufacturing context (general; no therapeutic claims)

• Pteridin-4-ol is a research chemical and not an approved excipient. It is more commonly a synthetic intermediate or reference scaffold in discovery chemistry.
• In preformulation research, related heteroaromatics may be assessed for physicochemical properties (pKa, solubility, stability) to inform design of pteridine-based leads.
• Salt formation/co-crystals: While the neutral heterocycle is weakly basic/acidic, salt or co-crystal strategies (e.g., with acids/bases or H-bond donors) can be explored to modulate solubility for experimental purposes.

Compendial status and GMP

• No pharmacopeial monograph is known for Pteridin-4-ol. Any use in regulated settings would require internal specifications, validated analytical methods, and GMP procurement.

Item-specific excipient/compendial details: Not specified for this item; refer to CoA/Spec Sheet.

For research use only: This product is supplied strictly for laboratory research. It is not intended for human or veterinary use, diagnostic procedures, or as a drug substance/excipient.

Physical Properties

Item-specific specifications

• Boiling point, melting point, density, refractive index, water/peroxide content, metal limits, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general data (for reference; not item-specific)

• Physical state: typically a crystalline solid for pteridinones/pteridinols.
• Melting behavior: many simple pteridin-4-one/4-ol systems display high melting points (>250 °C, often with decomposition) in the literature; specific values for pteridin-4-ol are scarce and tautomer/protonation/salt form dependent.
• pKa: pteridine cores are weakly basic at ring nitrogens and can exhibit lactam–lactim (keto–enol) tautomerism; reported microscopic pKa values for related pteridinones are typically <2 (very weak bases) and/or >10 for conjugate acids of lactim forms (literature). Use caution—exact pKa for this structure depends on conditions.
• LogP: Expected to be very low (high polarity, multiple nitrogens), often logP < 0 for simple pteridinones (literature trend). Exact value for pteridin-4-ol not located.
• Solubility: generally low in neutral water but improves in polar aprotic solvents (DMSO, DMF) and under acidic/basic conditions that shift tautomer/protonation (literature observations).

Practical implications

• Expect limited volatility and thermal robustness up to the onset of decomposition.
• Dissolution for analytical work is commonly achieved in DMSO or aqueous buffers adjusted to aid ionization; verify compatibility with your assay matrix.

Quality & Grades

Item-specific grade/purity

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

Guidance on grades (general; for context)

• Research grade: suitable for most discovery chemistry and method development. When UV, trace metal, or residual solvent limits matter (e.g., analytical assays, catalysis), request HPLC grade/low-UV or trace-metal screened materials.
• Pteridin-4-ol is sensitive to tautomeric state; specifications may include assay by qNMR/HPLC, water content (KF), and identity confirmation (1H/13C NMR, HRMS). If your application is sensitive to water or trace acids/bases (e.g., in metal-catalyzed couplings), verify those limits on the CoA.
• Stabilizers: none are typically used for simple heteroaromatic solids; if a stabilizer or salt form is present, it will be stated explicitly on the CoA.

Recommendations

• For reproducible medicinal and materials chemistry, obtain the CoA lot-specific purity, residual solvent profile, and, if relevant, polymorphic/salt information.
• If using for quantitative reference work, consider secondary verification (qNMR against a primary standard) and document the tautomeric composition under your assay conditions.

Reaction & Applications

Research context (general for pteridine chemistry)

• Scaffold role: Pteridin-4-ol (tautomeric with pteridin-4-one) is a minimalist member of the pteridine family central to many bioactive cofactor frameworks (pterins, folates). As a research building block, it serves as a core for derivatization at ring positions (e.g., 2, 6, 7) to access functionalized pteridines.

Representative transformations (literature)

• Electrophilic functionalization: N-oxidation at ring nitrogens using peracids (m-CPBA) or H2O2/UHP systems affords N-oxides that can be leveraged for directing effects or further rearrangements.
• Halogenation/activation: Vilsmeier–Haack or POCl3/POBr3 can convert the 4-one to 4-chloro derivatives (from related pteridinones), enabling subsequent SNAr with amines/alkoxides.
• Nucleophilic aromatic substitution (SNAr): electron-deficient pteridines undergo SNAr at activated positions (typically 4- or 6-halides), permitting introduction of amines, alkoxides, or thiolates.
• Metalation/cross-coupling: For halogenated pteridines, Pd-catalyzed Suzuki/Miyaura, Buchwald–Hartwig amination, or Sonogashira couplings expand substitution patterns.
• Lithiation: Directed metalation (e.g., with s-BuLi/TMEDA at low temperature) has been used on related diazines to introduce formyl or other electrophiles; substrate control is crucial due to multiple nitrogens.

Practical tips

• Dry, oxygen-controlled conditions are generally not mandatory for the parent heterocycle but are advised for sensitive intermediates (e.g., 4-chloro analogs).
• Control tautomer/protonation with solvent and base to bias reactivity (lactam vs lactim). Monitor by NMR to ensure desired form prior to key steps.
• Workup: chelating nitrogens can bind metals; include EDTA washes when purifying post-catalysis.

Reaction Conditions

General literature guidance (not item-specific; optimize for your substrate)

• N-oxidation: m-CPBA (1.1–1.5 equiv) in CH2Cl2 or MeCN at 0–25 °C for 2–16 h affords pteridine N-oxides; monitor by TLC/HPLC. Alternative: UHP (urea–H2O2) with TFAA in MeCN.
• 4-Position activation: Treat the 4-one tautomer with POCl3 (3–6 equiv) at 60–90 °C for 2–6 h to yield 4-chloro intermediates (reported for related pteridinones). Quench cautiously; neutralize and extract.
• SNAr on 4-/6-chloro derivatives: amines (1.5–3 equiv) in DMF/DMSO with K2CO3 or DIPEA, 60–120 °C, 2–18 h. Catalysis (Cu or Pd) can lower temperature and broaden scope.
• Cross-coupling: For aryl/alkenyl halides on the ring, Suzuki–Miyaura (Pd(dppf)Cl2, K2CO3, dioxane/H2O, 60–100 °C) or Buchwald–Hartwig amination (Pd2(dba)3/XPhos, NaOtBu, toluene or dioxane, 80–110 °C).
• Metalation/formylation: s-BuLi/TMEDA at −78 to −40 °C in THF, then DMF quench to install CHO at activated positions (reported on diazines). Strictly anhydrous/low-temperature handling required.

Workup/purification

• Due to strong basic sites, products may retain metals; use silica gel with 1–5% triethylamine or reverse-phase chromatography. Metal scavengers (SiliaMetS) are helpful post-coupling.

Yields

• Highly substrate dependent; literature reports for SNAr/couplings on pteridine cores commonly range 40–85% after optimization. Confirm on your system by small-scale screens.

Safety & Handling

Item-specific safety information

• GHS classification, signal word, pictograms, and H-statements: Not specified for this item; refer to SDS.

General safety guidance (literature/best practice; not a substitute for the SDS)

• Anticipated hazards: organic heteroaromatic solid; may cause eye/skin/respiratory irritation. Avoid dust generation and inhalation.
• Personal protective equipment (PPE): lab coat, safety glasses/goggles, and appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood when handling powders or preparing solutions.
• Incompatibilities: strong oxidizers may react with electron-rich sites; strong acids/bases can alter tautomeric state and potentially lead to degradation under forcing conditions. Avoid contact with reactive acylating/chlorinating agents unless intended for synthesis.
• Thermal stability: heteroaromatic solids typically decompose at elevated temperature; avoid heating above necessary process temperatures.
• First aid overview: in case of skin/eye contact, rinse with water for at least 15 minutes and remove contaminated clothing; if inhaled, move to fresh air; if ingested, rinse mouth. Seek medical attention in all cases. Follow institutional protocols.
• Spill/cleanup: avoid dust; sweep carefully or use HEPA vacuum. Dispose according to local regulations.

Always consult the product’s SDS for authoritative hazard classification, exposure limits, and emergency measures specific to this item.

Solvent Selection

Compound class–driven considerations (general)

• Polarity: electron-deficient, multi-heteroatom heteroaromatic; expects strong hydrogen-bond acceptor behavior and potential H-bond donation in the 4-ol (lactim) form.
• Miscibility/solubility (literature trends):
  • High solubility: DMSO, DMF, NMP.
  • Moderate/variable: methanol, ethanol, aqueous buffers at low pH (protonation) or high pH (deprotonation of the 4-ol form).
  • Low: nonpolar hydrocarbons (hexanes, toluene) unless derivatized.
• Dielectric considerations: polar aprotic solvents facilitate dissolution without competing H-bond donation, often beneficial for N-oxidation or electrophilic substitution chemistry on pteridines.

When to choose which solvent

• Analytical stock solutions: DMSO (common for plate-based assays) or DMF to prepare concentrated stocks (10–100 mM), then dilute into assay medium.
• Nucleophilic substitutions/activations on the ring: polar aprotics (DMF/DMSO) with inorganic bases can enhance reaction rates.
• Electrophilic functionalization (e.g., N-oxidation): dichloromethane or acetonitrile are typical media for peracid oxidations; ensure substrate solubility.

Comparison (general)

• DMSO vs DMF: DMSO offers superior solubility and benign volatility but can participate in oxidations at high temperature; DMF is easier to remove but degrades with strong base/heat.
• Aqueous buffers: useful for biophysical studies; adjust pH to control tautomer/protonation, noting potential for hydrolysis under extreme conditions.

Item-specific solubility: Not specified for this item; verify experimentally under your conditions.

Storage & Reconstitution

Item-specific storage

• Storage conditions: Room temperature (per Product Data). Protect from moisture and direct light. Keep container tightly closed.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

Reconstitution and solution handling (general guidance)

• Solvents: DMSO, DMF, or aqueous buffer adjusted for solubility (acidic/basic as appropriate). Start with small volumes and sonication if needed.
• Typical stock concentrations: 10–100 mM in DMSO for screening; record exact concentration by weight-in/volume or by UV/qNMR if available.
• Filtration: Use PTFE or PVDF syringe filters (0.22–0.45 µm) for particulate removal.
• Stability of solutions: Assess by LC–MS/HPLC over time; store working solutions at 2–8 °C short term or −20 °C for longer term, protected from light. Avoid repeated freeze–thaw by aliquoting.

Disposal

• Follow institutional and local regulations for disposal of nitrogen-containing heteroaromatics and organic solvents.

Notes

• Because key specifications (purity, water content) are not provided here, consult the lot-specific CoA for best practices on storage duration and any stabilizer information.
• Research use only, as stated by the manufacturer.

Structure & Identity

Item-specific identifiers (from Product Data)

• SKU: P1073199
• Product name: Pteridin-4-ol
• CAS: 700-47-0
• Storage: Room temperature
• InChIKey (as provided): 371268 (note: this is not a standard 27-character InChIKey; consult CoA/SDS for the definitive identifier)

Literature/computed identifiers and structural description (for reference; not item-specific specs)

• Molecular formula (literature, for the 4-oxo/4-ol tautomeric pair): C6H4N4O
• Molecular weight (literature): ~148.12 g/mol
• Preferred tautomeric description: pteridin-4(3H)-one ↔ pteridin-4-ol (keto–enol tautomerism at C4)
• SMILES (literature, example for 4-one tautomer): O=c1[nH]c2nccnc2nc1 (other depictions and protonation states exist)
• InChIKey (literature, for closely related records) varies by tautomer/protonation; verify before use in informatics workflows.

Structural features (general)

• The molecule is a fused bicyclic heteroaromatic system (pyrimidine fused to pyrazine), collectively termed a pteridine.
• Four ring nitrogens confer strong hydrogen-bond accepting capacity; the 4-ol/4-one site introduces an additional H-bond donor/acceptor capability depending on tautomer and pH.
• Planar, rigid, electron-deficient heteroaromatic core; high heteroatom density promotes π–stacking and coordination to metal centers.
• 2D description: two six-membered rings share an edge; heteroatoms are positioned such that the ring system is significantly electron-poor relative to benzene.

Notes

• Exact registries, SMILES, and InChI/InChIKey should be selected to match the specific tautomer/protonation intended; confirm against the Certificate of Analysis (CoA) for this item.

Synthetic Utility

Core reactivity (general for pteridin-4-one/4-ol systems)

• Functional handles: multiple ring nitrogens (Lewis basic sites) and the 4-oxo/4-hydroxyl functionality enable diverse transformations—N-oxidation, N-alkylation/acylation (on suitably activated nitrogens), and ring-halide installation for SNAr.
• Electron-deficient ring: facilitates SNAr at positions bearing good leaving groups (e.g., 4- or 6-chloro), enabling convergent introduction of amines, alkoxides, thiols.
• Annulation/condensation: the pteridine nucleus can be elaborated via cyclocondensation from 2,4,5-triaminopyrimidines and dicarbonyls; conversely, Pteridin-4-ol may serve as a late-stage platform for diversification rather than ring construction.

Named/related strategies (literature)

• Vilsmeier activation of the 4-one to 4-chloro-pteridines; subsequent Buchwald–Hartwig amination to access 4-arylamino derivatives.
• Minisci-type radical additions on protonated pteridines are less common but documented on related diazines; conditions require strong oxidants and careful control.
• Directed metalation/electrophile trapping at C-2/C-6 on related di-aza aromatics; choice of base/ligand dictates regioselectivity.

Applications

• Scaffold for libraries targeting pteridine-binding enzymes.
• Precursor to fluorescent pterin analogs (after ring functionalization/oxidation) for biochemical probes.

Practical notes

• Protect or control the 4-oxo/4-ol functionality when conditions risk over-chlorination or ring opening.
• The core can chelate with transition metals; include metal scavenging during purification after cross-couplings.

Target Specificity

Not applicable. This product is a small-molecule heteroaromatic, not an antibody or biological reagent with defined antigen/epitope specificity.

Item-specific target/clone/isotype data: Not applicable and not provided for this item.