2-Mercaptopteridin-4-ol - ≥95% , CAS No.52023-48-0

CAS: 52023-48-0 Cat. No.: M1064815 Numero EC: 257-612-8 PubChem CID: 919948

QUALITÀ & PUREZZA ≥95%

Storage

Room temperature

Specifiche

Specifiche e purezza

≥95%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥95%

Nomi e identificatori

Sorrisi canonici

C1=CN=C2C(=N1)C(=O)NC(=S)N2

IUPAC Name

2-sulfanylidene-1H-pteridin-4-one

InChIKey

VSPCYUNOZPCHLL-UHFFFAOYSA-N

INCHI

1S/C6H4N4OS/c11-5-3-4(8-2-1-7-3)9-6(12)10-5/h1-2H,(H2,8,9,10,11,12)

Isomeri SMILES

C1=CN=C2C(=N1)C(=O)NC(=S)N2

CAS alternativo

52023-48-0

PubChem CID

919948

Numero NSC

45766

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Classe: Pteridines and derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Pteridines and derivatives
• Alternative Parents: Pyrimidones Pyrimidinethiones 2-Thiopyrimidines Pyrazines Vinylogous amides Heteroaromatic compounds Thioureas Lactams Azacyclic compounds Organopnictogen compounds Organooxygen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Pteridine - 2-thiopyrimidine - Thiopyrimidine - Pyrimidinethione - Pyrimidone - Pyrazine - Pyrimidine - Heteroaromatic compound - Vinylogous amide - Lactam - Thiourea - Azacycle - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Aromatic heteropolycyclic compound
• Descrizione: 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

Proprietà chimiche e fisiche

• Peso molecolare: 180.190 g/mol
• XLogP3: -0.400
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 180.011 Da
• Monoisotopic Mass: 180.011 Da
• Topological Polar Surface Area: 99.000 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 232.000
• 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

There are no vendor-validated application protocols for this small-molecule building block.

• General handling for solution preparation (research-use context):
  • Prepare a concentrated stock (e.g., 10–100 mM) in dry DMSO or DMF. Filter through a 0.22 µm PTFE syringe filter if particulates are present.
  • For aqueous assays, dilute the organic stock into buffer with vigorous mixing; final DMSO content typically kept ≤1–2% v/v for enzyme assays (optimize per system).
  • If higher aqueous solubility is required, adjust pH to basic range (formation of thiolate/phenolate) or use cosolvents/surfactants compatible with the assay.
• Synthetic protocol notes:
  • For S-alkylation: Dry glassware, inert atmosphere, mild base (K2CO3) in DMF/MeCN; add electrophile dropwise; monitor by TLC/LC–MS; quench, extract, and purify.
  • For metal-catalyzed C–S coupling: Degas solvents, employ appropriate ligand/base, and maintain anhydrous conditions.

These are general suggestions only; develop lab-specific SOPs and consult the primary literature.

Biological Roles

• Item-specific biological data: Not specified for this item; for research use only.

• General context (literature; no therapeutic claims):

  • Pteridine scaffolds constitute the core of biologically significant compounds such as pterins, tetrahydrobiopterin (BH4), and folate derivatives. While 2-mercaptopteridin-4-ol is a synthetic derivative, its ring system mirrors these cofactors’ electronic properties, making it useful in biochemical model studies.
  • Mercapto and hydroxy substituents provide handles for conjugation to proteins, nucleic acids, or solid supports, enabling design of affinity probes or mimicry of enzyme–cofactor interactions in vitro.
  • The heteroatom-rich ring can participate in hydrogen bonding and metal coordination, features exploited in enzyme binding studies and fluorescence investigations (pteridines often show intrinsic absorbance/fluorescence; intensity and wavelength are substitution-dependent).
  • Redox and tautomeric behavior influence recognition by enzymes that process pteridines (e.g., dehydratases, oxidases) in model systems, although direct biological activity of this specific derivative is not established here.

• Use limitations:

  • No clinical/diagnostic use is stated or implied. Any biological experimentation should validate purity, stability, and solution state (thiol vs thione) to ensure interpretability of results.

Buffer Applications

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

• Practical note:
  • If introduced into buffered aqueous systems for assays, maintain pH control to manage deprotonation of the S–H/O–H groups (commonly pH ≥ 8 increases solubility via thiolate/phenolate formation). Avoid buffers with transition metals that might complex with thiolates unless intended.
  • Prepare concentrated stocks in DMSO or DMF and dilute into the target buffer with rapid mixing to prevent local supersaturation/precipitation.

No item-specific buffer recipes are provided for this product.

Green Alternatives

Because the compound is a solid building block rather than a process solvent, “greener alternatives” focuses on solvent/base choices and reaction modalities when using 2-mercaptopteridin-4-ol.

• Greener solvent choices (general literature):

  • Replace DMF/NMP with safer polar aprotics where feasible: Cyrene, propylene carbonate, or dimethyl carbonate (depending on reaction type/solubility).
  • Swap chlorinated solvents with MeTHF, CPME, or ethyl acetate for extractions and some alkylations.
  • For biochemistry/screening stocks, consider aqueous cosolvent systems (≤20–30% DMSO) to reduce neat DMSO use.

• Base and activation strategies:

  • Use inorganic carbonates (K2CO3, Cs2CO3) or bicarbonate in green solvents instead of strong soluble organic superbases, when compatible with selectivity.
  • Employ phase-transfer catalysis to lower solvent volumes and temperatures.

• Process intensification:

  • Microwave or flow conditions can reduce reaction times and energy input for S-alkylation/SNAr steps.

• Tradeoffs (balanced view):

  • Greener solvents may reduce solubility of this heteroaromatic, impacting rates/selectivity.
  • Carbonate bases may shift S/O-alkylation selectivity differently than stronger bases; optimization is required.

Comparison (general):

• DMF vs Cyrene: Cyrene offers better environmental profile and lower toxicity but may be less stable under strong base and requires water control.
• DCM vs EtOAc/CPME: EtOAc/CPME are greener and often effective, but DCM sometimes affords superior phase separation and solubility for highly polar intermediates.

Pharmaceutical Uses

• Item-specific pharmacopeial status/excipient role: Not specified for this item; refer to CoA/Spec Sheet. This product is supplied strictly for research use only.

• General R&D context (no therapeutic claims):

  • Pteridine derivatives are frequently explored as scaffolds in medicinal chemistry due to their hydrogen-bonding topology and electron-deficient ring system. A 2-mercapto/4-hydroxy substitution pattern allows prodrug or bioisostere strategies (e.g., S-alkyl prodrugs, thioether–sulfone oxidation series) during hit-to-lead campaigns.
  • The compound may serve as a reference standard or synthetic intermediate when assembling libraries targeting enzymes that bind pterins/folates (in vitro only).
  • Formulation screening (preclinical research): stock solutions are often prepared in DMSO for biochemical assays; solid form characterization (XRPD/DSC/TGA) is recommended to understand polymorphism and stability.

No regulatory, GMP, or clinical use information is asserted for this item.

Physical Properties

• Item-specific specs (this lot):

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Melting point: Not specified for this item; refer to CoA/Spec Sheet.
  • Boiling point: Not applicable (decomposes before boiling is typical for pteridine solids; literature note only).
  • Density: Not specified for this item; refer to CoA/Spec Sheet.
  • Solubility (spec): Not specified for this item; refer to CoA/Spec Sheet.
  • LogP, pKa, refractive index: Not specified for this item; refer to CoA/Spec Sheet.

• General/literature guidance (not item-specific; for planning only):

  • Physical state: Typically an off-white to yellow crystalline solid for pteridine thiols; may exhibit polymorphism and tautomer-dependent color.
  • Solubility tendencies: Low to moderate in water at neutral pH; readily soluble as the thiolate/phenolate salts in basic aqueous media; generally soluble in polar aprotic solvents (DMSO, DMF, NMP) and alcohols upon gentle warming.
  • Acid–base: S–H and O–H groups are weakly acidic; deprotonation is facilitated in polar aprotic media with mild base (e.g., K2CO3, DBU) for S/O-alkylation chemistry.
  • Stability: Aromatic heterocycles of this class can undergo slow air-oxidation of thiol to disulfide or thione forms; protect from strong oxidants and prolonged UV exposure.

All numeric values not explicitly stated above are not specified for this item; consult the CoA/SDS for definitive specifications.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
• Implication of unspecified grade:
  • Without a stated research, analytical, or specialty grade, performance attributes such as trace metal content, UV cut-off, residual solvents, and chromatographic baseline behavior are not defined here. Confirm via the CoA for your application (e.g., photophysics, metal-catalyzed coupling, bioassay screening).
• Considerations for pteridine derivatives (general):
  • Tautomer/oxidation state: Minor populations (thiol vs thione; 4-ol vs 4-one) can affect NMR and reaction selectivity. Suppliers may control this via synthesis and drying profiles—verify by NMR/HRMS.
  • Trace metals: If planning metal-catalyzed C–S/C–N coupling, low metal background is desirable; request ICP data if critical.
  • Chromatographic purity: For fluorescence/photophysics on pteridines, low UV-absorbing impurities are advantageous; HPLC trace requested as needed.
• Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. If no stabilizer is present, minimize air/oxidant exposure during storage.
• Documentation: Lot-specific CoA and SDS provide definitive specifications and test methods (e.g., HPLC area %, NMR, water content).

Reaction and Applications

Applications below are literature/general for 2-mercapto/4-hydroxy pteridine scaffolds; no item-specific claims are made.

• Nucleophilic derivatization:
  • S-alkylation/acylation: Generation of thioethers and thioesters via base-promoted reactions with alkyl halides, sulfonates, or acid chlorides. Selectivity between S- and O-alkylation can be tuned by base, solvent, and counterion.
  • O-alkylation: Protective group strategies at C4 (e.g., methylation) to direct downstream ring functionalization.
• Heteroaryl chemistry on the pteridine core:
  • SNAr on activated positions of the pteridine ring (literature) enables C–N, C–O, or C–S substitution; electron-withdrawing nature of the ring and ring nitrogens facilitate these transformations.
  • N-oxidation or ring N-alkylation to access pteridine N-oxides or quaternized salts, modulating electronics and solubility.
• Coordination/Materials:
  • The S, O, and N donors enable chelation to soft/hard metals; useful in preparing coordination complexes for catalysis or sensing (general literature).
• Biochemical tool development:
  • Pteridine motifs underpin cofactors (e.g., pterins, folates). Mercapto substitution provides a handle to tether the scaffold to probes, resins, or surfaces for enzyme/cofactor mimic studies (research-use context only).
• Practical tips:
  • Dry, oxygen-poor conditions improve yields for S-alkylations and metal-mediated C–S cross-couplings.
  • Monitor tautomer ratio by NMR (DMSO-d6 vs CD3OD) as it can influence reactivity and spectral interpretation.

Reaction Conditions

General literature guidance for transformations of 2-mercapto/4-hydroxy pteridines (not item-specific; optimize per substrate):

• S-Alkylation (to thioethers):

  • Base/solvent: K2CO3 (2–3 equiv) in DMF, MeCN, or acetone; or Cs2CO3 in MeCN.
  • Temperature/time: 20–60°C, 1–16 h, depending on electrophile reactivity.
  • Notes: Dry, oxygen-poor conditions improve outcomes. Halide > sulfonate > alcohol (with activation). Monitor S vs O selectivity; stronger base and polar aprotics often enhance S-alkylation.

• S-Arylation:

  • SNAr: Activated aryl fluorides with electron-withdrawing groups (–NO2, –CN, –CF3) in DMSO/DMF, 60–120°C, inorganic base (K2CO3/Cs2CO3).
  • Pd-catalyzed C–S coupling: Pd2(dba)3 (1–2 mol%), bulky monophosphine (XPhos, tBuXPhos), base (K3PO4), PhMe/1,4-dioxane or CPME, 80–110°C.
  • Cu-catalyzed Ullmann-type: CuI (5–10 mol%), diamine ligand, K2CO3 in DMSO, 80–120°C.

• O-Alkylation/Acylation:

  • Milder bases (K2CO3, NaH) in acetone/MeCN; 0–25°C for sensitive electrophiles to bias O- over S-alkylation.

• Protection/deprotection:

  • S-protection as thioethers or thioesters; O-protection as ethers/carbonates; typical acid/base or hydrogenolysis conditions for removal depending on protecting group.

• Workup/purification:

  • Quench with aqueous NH4Cl/NaHCO3; avoid strong oxidants. Purify by silica gel with antioxidants/reduced oxygen if needed; reverse-phase HPLC for highly polar products.

All conditions above are literature-general guidelines; verify on small scale.

Safety and Handling

• GHS classification and hazard statements (item-specific): Not specified for this item; refer to SDS for authoritative information.
• Signal word and pictograms: Not specified for this item; refer to SDS.
• General laboratory precautions (best practice for heteroaryl thiols/phenols; literature guidance):
  • PPE: Wear lab coat, safety glasses, and suitable gloves (e.g., nitrile). Handle in a fume hood to avoid dust inhalation.
  • Avoid: Strong oxidizers (may oxidize thiol), strong acids/bases without process control, and prolonged exposure to air/UV if oxidation is a concern.
  • Incompatibilities: Oxidizing agents, acid chlorides/anhydrides (acylation), and soft metal salts that can form strong complexes with thiolates.
  • Special risks: Thiols may have noticeable odor; minimize open handling. Some mercaptoheterocycles can slowly oxidize to disulfides/thiones—store tightly closed.
• First-aid overview (general):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: Rinse with water for ≥15 minutes; remove contaminated clothing; obtain medical advice if irritation continues.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Fire-fighting (general): Use CO2, dry chemical, or foam. Combustion may produce NOx/SOx; firefighters should wear SCBA.
• Spill response: Avoid dust formation; collect with inert absorbent; dispose according to local regulations.

Always consult the product-specific SDS for binding safety guidance.

Solvent Selection

This compound is a heteroaromatic thiol/phenol; selection of solvent often balances solubility, reactivity, and tautomer control.

• Polarity/miscibility (general, literature):
  • Preferred dissolution: Polar aprotic solvents (DMSO, DMF, NMP) typically afford the highest solubility; alcohols (MeOH, EtOH, i-PrOH) can be suitable with warming.
  • Aqueous media: Limited solubility at neutral pH; solubility increases markedly upon basification (formation of thiolate/phenolate). Buffer selection should consider potential metal ion content (avoid unintended complexation/oxidation).
• Choosing among common options (general guidance):
  • DMSO: Excellent solvent for stock solutions for screening/biochemistry; miscible with water; minimize freeze–thaw.
  • DMF/NMP: Useful for S-alkylation and SNAr; high dielectric constant aids deprotonation and nucleophilicity.
  • Alcohols/acetone/MeCN: Viable for milder alkylations with inorganic bases (e.g., K2CO3) when solubility permits.
• Practical tips:
  • Degas/argon-sparge for air-sensitive transformations (to limit thiol oxidation).
  • For analytical work (HPLC/LC–MS), equilibrate with modifier (0.1% formic acid or ammonium acetate) as needed to manage peak shape and ionization, recognizing potential acid/base sensitivity.
• Comparison snapshot (general):
  • DMSO vs MeOH: DMSO offers higher solubility and base compatibility; MeOH is greener and easier to remove but may participate in H-bonding and transesterification side reactions in some systems.

Storage and Reconstitution

• Item-specific storage and shipping:

  • Storage Conditions: Room temperature (as provided in Product Data).
  • Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

• General storage guidance (heteroaryl thiol/phenol solids):

  • Keep container tightly closed in a dry, inert atmosphere if possible. Protect from strong light and oxidants to minimize thiol oxidation.
  • For long-term storage, consider desiccation and/or nitrogen backfill. Avoid repeated opening in humid environments.

• Reconstitution/preparation of stock solutions (general):

  • Solvents: DMSO or DMF typically provide highest solubility; alcohols may suffice with warming. For aqueous work, dissolve in minimal organic cosolvent, then dilute into buffer. Adjust pH (basic) if soluble salt formation is desired.
  • Concentration: Prepare working stocks appropriate to your assay (commonly 10–100 mM in DMSO); aliquot to minimize freeze–thaw.
  • Stability: Solutions in DMSO/DMF are generally stable for days at 2–8°C or –20°C when protected from air/light; verify by LC–MS before critical experiments.

• Research use note: For research use only. Consult the CoA and SDS for definitive handling and stability information.

Structure and Identity

Brief overview: 2-Mercaptopteridin-4-ol is a heteroaromatic pteridine derivative bearing a thiol at C2 and a hydroxyl at C4, capable of thione/thiol and keto/enol tautomerism.

• Item-specific identifiers (Product Data):
  • CAS: 52023-48-0
  • PubChem CID: 919948
  • InChIKey: 387341 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• Structural features (general/literature description of the scaffold):
  • Core: Pteridine bicyclic system (fused pyrimidine–pyrazine) with four ring nitrogens.
  • Functional groups: Heteroaryl thiol at C2 (mercapto) and phenolic/oxo functionality at C4 (4-ol/4-one tautomerism).
  • Tautomerism: 2-thiol ⇌ 2-thione and 4-ol ⇌ 4-oxo equilibria; relative populations depend on solvent polarity and pH (literature).
  • Acid–base behavior: Both S–H and O–H can deprotonate under basic conditions; the heteroaromatic ring nitrogens can participate in hydrogen bonding and coordination (literature).
• 2D description in words (general):
  • A planar, bicyclic diazine–diazine system with substituents at positions 2 (–SH) and 4 (–OH/═O), multiple endocyclic nitrogens positioned for intramolecular H-bonding and metal chelation. No stereocenters are present.

Synthetic Utility

• Functional group leverage:
  • Thiol (S–H): Versatile nucleophile enabling S-alkylation, S-arylation (e.g., via SNAr or metal-catalyzed couplings), thioester formation, and thio-Michael additions to activated alkenes (literature).
  • Phenol/4-oxo: Ambident reactivity for O-alkylation/acylation; can be protected to steer subsequent ring functionalization.
  • Heteroaromatic ring nitrogens: Sites for protonation/coordination; can modulate electronics by N-oxidation or quaternization.
• Retrosynthetic value:
  • Serves as a linchpin to access libraries of pteridine thioethers/ethers where substituent modulation tunes solubility, basicity, and photophysics.
  • Acts as a masked electrophile upon conversion to sulfenyl halides or via Mitsunobu-type O-alkylations (with appropriate alcohol partners).
• Named/representative transformations (literature):
  • S-Alkylation with alkyl halides under K2CO3/DMF or Cs2CO3/MeCN.
  • S-Arylation via SNAr with activated (fluoro)arenes or Pd-catalyzed C–S coupling (e.g., Pd2(dba)3/XPhos; CuI/diamine for Ullmann-type).
  • O-Alkylation under milder bases (K2CO3, NaHCO3) in polar aprotic solvents to control chemoselectivity.
• Selectivity control:
  • Base strength, cation (K+ vs Cs+), and solvent polarity influence S vs O alkylation; lower temperatures and less polar solvents often favor S-alkylation for soft electrophiles, but optimization is case-dependent.
• Analytical:
  • Track reactions by LC–MS; isotopic patterns (S, N) assist identification. Tautomerism may broaden NMR signals; use HMBC/HSQC for assignment.

Target Specificity

This product is a small-molecule building block, not a biological macromolecule or antibody. No antigen/epitope/clone/isotype information applies.

• Item-specific data: Not applicable.
• Guidance: For biochemical studies, any observed selectivity toward enzymes or receptors must be determined experimentally; no target specificity is provided with this catalog item.