Manufacturer: Hangzhou Royalchem Co.,LTD.
Website: www.cnroyalchem.com
【 Providing a complete set of intermediates and impurities for Ticagrelor 】
【 Providing a complete set of intermediates and impurities for Ticagrelor 】
【 Providing a complete set of intermediates and impurities for Ticagrelor 】
Here is a detailed product description for 5-Nitro-2-(propylthio)pyrimidine-4,6-diol (CAS 145783-13-7) :
1. Chemical Identity: * Chemical Name: 5-Nitro-2-(propylthio)pyrimidine-4,6-diol * Synonyms: * 5-Nitro-2-(propylthio)pyrimidine-4,6(1H,5H)-dione (Preferred IUPAC tautomeric name) * 5-Nitro-2-(propylthio)-4,6(1H,5H)-pyrimidinedione * 2-(Propylthio)-5-nitropyrimidine-4,6(1H,5H)-dione * 5-Nitro-2-(propylsulfanyl)-1H-pyrimidine-4,6-dione * CAS Registry Number: 145783-13-7 * Molecular Formula: C₇H₉N₃O₄S * Molecular Weight: 231.23 g/mol
2. Structural Characteristics: * Core Structure: Pyrimidine heterocycle (six-membered ring with two nitrogen atoms). * Substituents: * Position 2: Propylthio group (-S-CH₂-CH₂-CH₃). * Position 5: Nitro group (-NO₂). * Positions 4 & 6: Oxygen atoms (hydroxyl groups in the diol name, carbonyl groups in the predominant tautomeric dione form). * Tautomerism: Exists predominantly in the diketo (pyrimidinetrione) tautomeric form (5-Nitro-2-(propylthio)pyrimidine-4,6(1H,5H)-dione) rather than the dihydroxy form implied by "diol". This is the more stable and reactive form, especially for hydrogen bonding and metal chelation. The structure is often drawn with carbonyls at positions 4 and 6, and an imide NH between them.
3. Physical Appearance: Typically described as an off-white to yellow or light brown crystalline powder or solid . Color can vary slightly depending on purity and storage conditions.
4. Key Chemical Properties: * Reactivity Profile: * Electrophilic Centers: The carbon atoms adjacent to the nitro group (C4 and C6, especially as carbonyls) are electrophilic and susceptible to nucleophilic attack. * Acidic Protons: The imide N-H proton (between C4=O and C6=O) is relatively acidic (pKa likely in the range of ~8-10) due to the flanking electron-withdrawing carbonyl and nitro groups. The propylthio group has very weak acidity. * Nitro Group: A strong electron-withdrawing group, making the ring electron-deficient and activating positions towards nucleophilic substitution or addition. It can potentially be reduced to amino or other functional groups. * Thioether Linkage: The S-propyl group is a thioether. It can potentially be oxidized to sulfoxide or sulfone, or cleaved under strong reducing conditions. * Solubility: Expected to have low solubility in water . Likely soluble in polar organic solvents such as dimethyl sulfoxide (DMSO), dimethylformamide (DMF), and dimethylacetamide (DMAc). Moderately soluble in alcohols (e.g., methanol, ethanol) and acetonitrile. Likely insoluble in non-polar solvents (e.g., hexane, toluene).
5. Applications and Use: * Primary Use: Serves as a specialized chemical building block (synthon) in organic synthesis, particularly medicinal chemistry and agrochemical research. * Target Synthesis: Used primarily as an intermediate in the synthesis of more complex molecules, especially modified pyrimidine derivatives. * Potential Applications: Its structure suggests potential utility in developing compounds with biological activity, possibly as: * Inhibitors of enzymes like kinases or dihydrofolate reductase (DHFR) (given the pyrimidinetrione core similarity to barbiturates/dihydroorotate). * Candidates for antimicrobial, antiviral, or anticancer screening programs. * Ligands for metal coordination. * Research Focus: Valued as a template for introducing the 5-nitro-2-alkylthiopyrimidine-4,6-dione pharmacophore into target molecules, allowing for further derivatization (e.g., displacement of the thioether, reduction of the nitro group, functionalization at C4/C6).
6. Handling, Storage & Safety: * Stability: Generally stable under recommended storage conditions. However, light-sensitive and potentially moisture-sensitive . May decompose under strong acid/base conditions, high heat, or strong oxidizing/reducing agents. * Storage: Store in a cool, dry place . Keep container tightly closed and protected from light. Store under an inert atmosphere (e.g., nitrogen or argon) for long-term stability. Recommended storage temperature is often 2-8°C (refrigerated) . * Handling Precautions: Handle with care using appropriate personal protective equipment (PPE) including lab coat, safety glasses, and nitrile gloves. Use in a well-ventilated area (fume hood). * Hazard Considerations: * Health Hazards: May be harmful if swallowed, inhaled, or absorbed through skin. May cause skin, eye, or respiratory irritation. Potential sensitizer. The effects of chronic exposure are unknown. Treat as a potential health hazard. * Physical Hazards: Not typically classified as highly flammable or explosive under normal conditions, but organic nitro compounds should always be treated with caution regarding thermal stability. * Environmental Hazards: Data likely limited. Dispose of as hazardous chemical waste according to local regulations. Avoid release to the environment. * Safety Data Sheet (SDS): ALWAYS consult the specific, up-to-date Safety Data Sheet (SDS) provided by the supplier before handling or using this compound. The SDS contains critical information on hazards, first aid, firefighting, accidental release measures, exposure controls, and disposal.
