6-Phenyl-2-thiouracil-C,N , CAS No.P1451429

CAS: P1451429 Cat. No.: P1451429 Formula: C₉₁₃CH₈₁₅N₂OS Peso molecolare: 207.23

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Panoramica

6-Phenyl-2-thiouracil- 13 C, 15 N 2 is the 13 C, 15 N labeled 6-Phenyl-2-thiouracil.

Specifications

Condizioni di conservazione di stoccaggio

Store at -20°C

Spedito in

Ice chest + Ice pads

Questo prodotto richiede spedizione a catena fredda. I servizi di terra e altri servizi economici non sono disponibili.

Nomi e identificatori

Peso molecolare

207.23

Application Protocols

• No vendor-validated protocols, methods, or assay conditions are provided for this specific item. The following general practices apply to small-molecule research reagents of limited aqueous solubility:
  • Prepare a concentrated stock in dry DMSO (e.g., 10–50 mM). Warm gently (≤40 °C) and vortex/sonicate to fully dissolve; protect from light.
  • For biochemical assays, dilute the DMSO stock into buffer with vigorous mixing to a final DMSO content ≤1–2% v/v. Include vehicle-only controls.
  • For synthetic use, dry the solid under vacuum before moisture-sensitive steps; employ an inert atmosphere for metalation/alkylation chemistry.
  • Analytical QC before use: verify identity and purity by 1H NMR and LC/MS; for metalation studies, consider elemental analysis or ICP-MS of complexes.
• If you require a tested application or protocol, contact Technical Support with your use-case; we can share literature precedents matched to your conditions.

Biological Roles

• Item is designated for research use only. No clinical or diagnostic use is intended or implied.
• General biochemical context (literature):
  • 2-Thiouracil (s2U) is a known nucleobase modification in tRNA in biology, where sulfur at the 2-position modulates base pairing and thermal stability. While 6-phenyl substitution is non-natural, thiouracil scaffolds are widely used as probes to study nucleic acid photochemistry, H-bonding, and sulfur’s effect on base pairing.
  • Sulfur substitution alters absorption and intersystem crossing tendencies compared to uracil; thiocarbonyl groups can participate in triplet-state photochemistry and act as quenchers or photo-crosslinkers in nucleic acid/protein studies (compound- and substitution-dependent).
  • As heteroaromatic thioamides, these molecules can chelate soft metals, enabling biochemical tagging or spectroscopic studies of metallo–biomolecule interactions in vitro.
• Physicochemical determinants relevant to bioassays (general):
  • Increased hydrophobicity from a 6-phenyl group may enhance binding to hydrophobic pockets in model systems and affects membrane permeability in cell-free assays; however, solubility in aqueous buffers is typically poor without cosolvent (DMSO) or formulation.
• No target-specific biological activity, potency, or ADME data are specified for this catalog item. For any biological experiments, define concentration ranges empirically, begin with small-scale DMSO stock solutions, and include appropriate vehicle controls.

Buffer Applications

• This compound is not a buffering reagent and is not commonly used to prepare defined pH buffer systems.
• Practical guidance if used in aqueous assays (general):
  • Prepare concentrated DMSO stocks (e.g., 10–50 mM) and dilute into the desired biological buffer (e.g., PBS, HEPES) keeping final DMSO ≤1–2% v/v to maintain cell-free assay compatibility. Solubilizers (0.01–0.1% nonionic surfactant) can be considered in biophysical assays.
• Buffer recipes, pKa values, and buffering ranges are not applicable to this item. Item-specific aqueous solubility/compatibility: Not specified for this item; refer to CoA/Spec Sheet.

Green Alternatives

• Opportunities to reduce solvent and process footprint when working with thiouracil derivatives (general guidance):

  • Prefer lower-toxicity, biodegradable solvents when feasible. Replace high-boiling amide solvents (DMF, NMP, DMAc) with MeCN, 2-MeTHF, or EtOAc where solubility and reaction rates remain acceptable.
  • Avoid chlorinated solvents unless necessary for selectivity or workup efficiency.

• Example comparison (general; choose case-by-case):

  Greener option | Typical use | Trade-offs ---------------|-------------|---------- 2-MeTHF | Medium-polarity reactions, extractions | Limited solubility for very polar substrates; forms peroxides slowly—monitor Ethyl acetate | Workups, recrystallization | Lower polarity can limit dissolution; bp 77 °C Acetonitrile | Polar aprotic, many S-/N-alkylations | Toxicity concerns remain; good volatility/recovery EtOH/i-PrOH | Recrystallization, some condensations | May require heating; hydrogen-bonding can alter selectivity Supercritical CO2 (with co-solvents) | Particle engineering | Specialized equipment needed

• Process intensification:

  • Use micellar catalysis (aqueous surfactant media) for certain C–N/S–C couplings to cut organic solvent volumes (literature-dependent).
  • Implement solvent recovery and dry-loading on silica/alumina to minimize solvent use during chromatography.

• Note: The choice of “green” alternative must balance EHS gains with required solubility/reactivity for 6-phenyl-2-thiouracil chemistry.

Pharmaceutical Uses

• No pharmacopeial listing, excipient role, or GMP status is provided for this catalog item. It is supplied strictly for research use only.
• General formulation considerations for research materials of this class:
  • For in vitro assays, DMSO stock solutions are common; filter sterilize (0.22 µm PTFE) if sterility is required for cell-free systems. Avoid aqueous stocks unless solubility/stability are confirmed.
  • For solid-dosage research prototypes (non-clinical), co-milling with water-soluble carriers or inclusion complexes (e.g., cyclodextrins) can improve apparent solubility; these approaches are for exploratory lab work only.
  • Photostability: thio-carbonyl chromophores can be light-sensitive; protect solutions from light.
• Regulatory and clinical use: Not applicable. Do not use in humans or animals for therapeutic or diagnostic purposes.

Physical Properties

• Item-specific physical constants: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Literature/general expectations for 2-thiouracil derivatives (for planning only; not product specifications):
  • State: typically crystalline solids with limited volatility.
  • Solubility: poor in nonpolar solvents; improved solubility in polar aprotic solvents (e.g., DMSO, DMF, NMP) and under basic conditions due to deprotonation of ring N–H. Many thiouracil derivatives also show partial solubility in hot alcohols and acetonitrile. Actual solubility varies strongly with aryl substitution.
  • Acid–base behavior: ring N–H groups are weakly acidic; deprotonation can be promoted by strong bases (e.g., alkoxides, NaH) in anhydrous polar aprotics. The thioamide sulfur is nucleophilic and can be alkylated or oxidized.
  • Partitioning: incorporation of a phenyl ring raises hydrophobicity relative to uracil; however, heteroatom density still imparts some polarity. LogP is therefore moderate in many substituted thiouracils (literature, compound-dependent).
• Refractive index, density, bp/mp, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
• Note: Values above are general literature insights into thiouracil-class materials and are not specifications for SKU P1451429.

Quality and Grades

• Grade/Purity (catalog listing): Not specified for this item; refer to CoA/Spec Sheet for purity, assay method, and allowable impurity limits.
• What grade means (general guidance):
  • Research-grade heterocycles are typically qualified by HPLC/UPLC or NMR assay and controlled for key organic/elemental impurities. For nucleobase analogs, closely related isomers/tautomers and residual halogenated or sulfur-containing reagents may be monitored.
  • If HPLC grade or low-UV specifications are relevant (e.g., for photophysical studies), vendors typically control UV-absorbing impurities across 190–400 nm. This product’s UV specifications are Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers/additives: Not specified for this item; refer to CoA/Spec Sheet. In general, stabilizers are rarely used for solid thiouracils; dryness and protection from prolonged light/air are typical.
• Documentation and lot traceability:
  • For exact assay, residual solvents, metals, and water content, consult the lot-specific CoA. If needed, request additional analytical data (1H/13C NMR, HRMS, HPLC chromatogram, Karl Fischer) from Technical Support.
• Suitability:
  • For research use only (as stated). Not for human or animal diagnostic or therapeutic use.

Reaction and Applications

• Research applications (general, literature-based for 2-thiouracil scaffolds):
  • Ligand/chelate precursor: The “C,N” designation suggests utility as a cyclometalating ligand donor set. After directed C–H activation at the phenyl group, metalation can furnish C,N-chelated complexes with late transition metals (e.g., Pd, Pt, Ir) used in catalysis or photophysics.
  • Coordination via S/N: The thioamide sulfur and ring nitrogen(s) can bind as N,S chelates to soft metals (e.g., Au, Cu, Ag), enabling complex synthesis for materials chemistry.
  • Functionalization chemistry: The nucleophilic sulfur undergoes S-alkylation/acylation; N1/N3 positions permit N-alkylation (regioselectivity controlled by base/solvent). Oxidations at sulfur (→ sulfoxide/sulfone-like or thiourea-oxide analogs) tune electronics and H-bonding.
  • Cross-coupling platforms: If the aryl ring is pre-halogenated in a derivative, Suzuki/Negishi/Buchwald–Hartwig chemistry can be applied to build diversity around the 6-phenyl substituent (general strategy; not specific to this item’s current substitution pattern).
• Practical tips:
  • Tautomerism can influence electrophilic/nucleophilic reactivity; controlling pH/base and solvent polarity often improves selectivity for S- vs N-alkylation.
  • Exclude moisture/air for metalation steps; pre-dry reagents and degas solvents (freeze–pump–thaw or sparging).
  • For purification, normal-phase silica may retain strongly H-bonding thiouracils; reverse-phase or addition of polar modifiers (e.g., 1–5% MeOH/Et3N in DCM) can help elution.
• Manufacturer-stated applications: Not specified in the catalog entry; see above literature-based expansions for typical uses of the scaffold.

Reaction Conditions

• The following are literature/general conditions for common transformations of thiouracil scaffolds; they are not product specifications for SKU P1451429.
• S-alkylation:
  • Solvent: DMF, DMSO, MeCN. Base: K2CO3 or Cs2CO3 (2–3 equiv). Temperature: rt to 60 °C. Time: 1–12 h. Typical isolated yields: 60–90%, dependent on alkyl electrophile and sterics.
• N-alkylation (selectivity control):
  • Solvent: anhydrous DMF or THF. Base: NaH (60% in mineral oil) or t-BuOK (1.1–1.5 equiv). Temperature: 0 °C to rt, then warm to 40–60 °C if needed. Add electrophile slowly to favor kinetic site. Monitor by LC/MS. Yields commonly 40–80% depending on regioselectivity.
• Thionation (if preparing from uracil):
  • Reagents: Lawesson’s reagent (0.6–1.0 equiv) or P4S10/hexamethyldisiloxane. Solvent: toluene, xylene, or dioxane. Temperature: reflux (110–140 °C). Time: 2–16 h. Workup with aqueous bicarbonate and silica plug to remove phosphorus byproducts.
• Oxidation at sulfur:
  • Reagents: mCPBA (≤1.1 equiv for mono-oxidation). Solvent: DCM at 0 °C to rt. Time: 0.5–3 h. Control equivalents to avoid overoxidation.
• Metalation/coordination (C,N or N,S):
  • Metals: Pd(II), Pt(II), Ir(III), Cu(I). Solvent: dry MeCN, DCM, or alcohols; sometimes acetate or carbonate base, with inert atmosphere. Temperatures: rt to 80 °C. Times: 1–24 h. Characterize by NMR/HRMS/elemental analysis.
• Recrystallization/purification:
  • Solvents: EtOH/MeOH, EtOAc/hexanes mixtures, or MeCN. For strongly retained products, consider reverse-phase chromatography with water–MeCN + 0.1% formic acid or NH4OAc.

Safety and Handling

• GHS/CLP classification, signal word, H-statements, and pictograms: Not specified for this item; refer to the product SDS.
• General hazards for thiocarbonyl-containing heterocycles (literature/general):
  • May cause irritation to skin, eyes, and respiratory tract. Avoid dust generation and inhalation. Handle in a fume hood.
  • Thioamides can be harmful if swallowed; practice strict hygiene and avoid ingestion.
• PPE and engineering controls:
  • Use lab coat, safety glasses or splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Employ local exhaust ventilation/fume hood when weighing or dissolving.
• Incompatibilities and reactivity (general):
  • Strong oxidizers may oxidize the thioamide sulfur (to sulfoxide/sulfone-like products). Strong bases deprotonate ring N–H; strong acids protonate ring nitrogens and can promote hydrolysis under forcing conditions.
  • Avoid moisture ingress during moisture-sensitive transformations (metalation, anhydrous alkylations).
• First aid (summary; consult SDS for details):
  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: rinse with plenty of water for ≥15 minutes; remove contaminated clothing; seek medical advice if irritation continues.
  • Ingestion: rinse mouth; do not induce vomiting; obtain medical attention.
• Fire safety: If combustible organic solid, use CO2, dry chemical, or foam. Combustion can release sulfur- and nitrogen-oxides; wear SCBA for large fires.
• Always defer to the SDS for authoritative safety information for this specific item.

Solvent Selection

• Polarity class and miscibility (general):
  • 6-Phenyl-2-thiouracil derivatives are polar aromatic solids. They typically dissolve best in polar aprotic solvents such as DMSO, DMF, NMP, or DMAc; solubility in acetonitrile and alcohols can improve upon heating. Limited solubility is expected in nonpolar hydrocarbons and ethers.
• Practical solvent choices by task (general guidance):
  • NMR: DMSO-d6 is usually reliable; DMF-d7 can be used if DMSO broadens signals. Exchangeable N–H may appear broadened or shift with temperature.
  • S-alkylation/N-alkylation: anhydrous DMF, DMSO, or acetonitrile with appropriate base (Cs2CO3, K2CO3, NaH) are commonly used. Phase-transfer conditions in polar solvents can also work.
  • Metalation/coordination: to access C,N or N,S chelation motifs, use dry, oxygen-free polar aprotic media or coordinating solvents (THF, DME, MeCN) under inert atmosphere.
• When to choose alternatives:
  • For greener profiles or easier removal, consider MeCN or EtOAc when compatible; for high-temperature dissolutions, NMP/DMAc provide higher boiling points but are harder to remove.
• Solubility and solvent specifications for this catalog item: Not specified for this item; refer to CoA/Spec Sheet.

Storage and Reconstitution

• Storage (item-specific, from Product Data):
  • Store at −20 °C.
  • Shipped in an ice chest with ice pads to maintain a low temperature during transit.
• General handling and stability guidance:
  • Allow container to equilibrate to room temperature in a desiccator before opening to avoid moisture condensation.
  • Protect from prolonged exposure to light and air; store tightly sealed under dry conditions. If available, keep under inert gas blanket for long-term storage.
• Solution stability (general):
  • DMSO or DMF stock solutions are typically stable for days to weeks at −20 °C when protected from light and moisture. Prepare aliquots to minimize freeze–thaw cycles.
  • Aqueous solubility is usually low; if aqueous stocks are necessary, confirm stability by HPLC over intended use time.
• Reconstitution:
  • Not applicable to lyophilized proteins; for this small molecule, dissolve directly in an appropriate dry solvent (e.g., DMSO) to the desired concentration. Filter through a 0.2 µm PTFE syringe filter if particulate is observed.
• For definitive shelf-life and retest period, consult the lot-specific CoA/Spec Sheet.

Structure and Identity

• Item identity specifics (for this catalog lot):
  • CAS: P1451429 (internal placeholder)
  • Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• Structural description (general, based on chemical name):
  • 6-Phenyl-2-thiouracil corresponds to a uracil (pyrimidin-2,4-dione) core in which the C2 carbonyl is replaced by a thiocarbonyl (C=S), yielding a 2-thiouracil (thioamide-like) heterocycle. The “6-phenyl” substituent denotes a phenyl ring attached at the C6 position of the pyrimidine.
  • The ring system is a six-membered aromatic diazine (pyrimidine) with two endocyclic nitrogens (N1 and N3), one carbonyl at C4 (C=O), and one thiocarbonyl at C2 (C=S). The 6-phenyl substituent adds a second aromatic system capable of π–π interactions.
  • Tautomerism (general): 2-thiouracils can exhibit thione–thiol and lactam–lactim tautomerism; the predominant form under neutral conditions is typically the thione–lactam.
  • “C,N” in the name commonly denotes a cyclometalating donor set (C– and N–coordination) in organometallic chemistry; in this context, the ligand can, in principle, bind a metal through an anionic aryl carbon (from the phenyl ring, after C–H activation) and a ring nitrogen, although S/N coordination modes are also known. (Literature/general information.)

Synthetic Utility

• Functional group ensemble:
  • Thioamide (C=S) at C2 and amide (C=O) at C4 within a pyrimidine ring; two endocyclic nitrogens (N1, N3); appended phenyl at C6. This enables diverse chemoselective transformations.
• Typical transformations (literature/general):
  • S-alkylation/acylation: The sulfur is nucleophilic; alkyl halides, Michael acceptors, or acid chlorides in polar aprotic media with base (K2CO3, Cs2CO3) give S-substituted products.
  • N-alkylation: Under stronger basic conditions (NaH, t-BuOK), alkylation at N1 or N3 is possible; solvent and counterion help control regioselectivity. Protecting-group strategies (e.g., transient S-alkylation) can direct N-alkylation.
  • Oxidation: Stepwise oxidation at sulfur (e.g., mCPBA, Oxone) tunes electronics and H-bonding; overoxidation can alter ring stability—monitor by LC/MS.
  • Metal coordination/cyclometalation: Deprotonation followed by C–H activation on the 6-phenyl substituent can furnish C,N-chelates with Pd/Ir/Pt; N,S chelation to softer metals is also well documented.
  • Electrophilic aromatic substitution on the phenyl ring (nitration, halogenation) enables further cross-coupling diversification.
• Retrosynthetic value:
  • 6-Phenyl-2-thiouracil can be derived from 6-phenyluracil via thionation (Lawesson’s reagent, P4S10) at C2, or by installing the 6-phenyl unit onto a thiouracil core via cross-coupling of a 6-halogenated thiouracil with an aryl boronate.
• Utility summary: Versatile scaffold for ligand development, materials, and nucleobase-analog chemistry.

Target Specificity

• Not an antibody, enzyme, or targeted biological reagent. No antigen/epitope, clone, isotype, or species reactivity applies to this product.
• Any target engagement in research (e.g., metal binding, nucleic acid interactions) is context- and assay-dependent and not specified for this item.