Tetraphenylfuran - ≥95% , CAS No.1056-77-5

CAS: 1056-77-5 Cat. No.: T1029804 Formula: C₂₈H₂₀O Peso molecolare: 372.500 Numero EC: 661-577-8

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=CC=C(C=C1)C2=C(OC(=C2C3=CC=CC=C3)C4=CC=CC=C4)C5=CC=CC=C5
• IUPAC Name: 2,3,4,5-tetraphenylfuran
• InChIKey: FWLFKBDHSBFSMW-UHFFFAOYSA-N
• INCHI: 1S/C28H20O/c1-5-13-21(14-6-1)25-26(22-15-7-2-8-16-22)28(24-19-11-4-12-20-24)29-27(25)23-17-9-3-10-18-23/h1-20H
• Peso molecolare: 372.500

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Benzene and substituted derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzene and substituted derivatives
• Alternative Parents: Heteroaromatic compounds Furans Oxacyclic compounds Organooxygen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Monocyclic benzene moiety - Heteroaromatic compound - Furan - Oxacycle - Organoheterocyclic compound - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Aromatic heteromonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
• 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: 372.500 g/mol
• XLogP3: 7.600
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 372.151 Da
• Monoisotopic Mass: 372.151 Da
• Topological Polar Surface Area: 13.100 Ų
• Heavy Atom Count: 29
• Formal Charge: 0
• Complexity: 433.000
• 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

• Not applicable. No tested biological assay formats (e.g., WB, IHC, IF, FC) are associated with this small-molecule product in the provided data.
• For materials or spectroscopy workflows (general suggestions):
  • Prepare stock solutions in dry CH2Cl2, toluene, or chlorobenzene; filter through 0.2 µm PTFE prior to film casting or spectroscopy.
  • For thin films, optimize spin speeds and solvent mixes to tune thickness and morphology; anneal under inert atmosphere if required.
• Note: These are general research tips, not validated protocols for this specific catalog item.

Biological Roles

• Not typically applicable.
  • Tetraphenylfuran is a synthetic, hydrophobic polyaromatic research chemical without known endogenous biological roles or metabolic functions.
  • In biochemical research it may be used only as an inert chromophore or hydrophobic scaffold in model systems; no biological activity is implied.
  • For all biological or cell-based work, ensure appropriate solvent carriers (e.g., DMSO with low final percentages) and include vehicle controls due to poor aqueous solubility.

Buffer Applications

• Not typically applicable.
  • As a neutral, water-insoluble polyaromatic solid, tetraphenylfuran is not used as a buffering agent and does not participate in common laboratory buffer systems. Consider this section not relevant; see Solvent Selection and Reaction & Applications for guidance more suitable to this compound type.

Green Alternatives

• Applicability
  • As a solid polyaromatic building block, “solvent and process” choices drive the green profile more than the substrate itself.
• Greener processing strategies (literature/general)
  • Prefer non-chlorinated aromatic solvents (e.g., toluene, anisole) where solubility/performance allow; replace CH2Cl2/CHCl3 with ethyl acetate or CPME for workups and chromatography when feasible.
  • Employ mechanochemical or solvent-minimized coupling methods (ball milling or high-solids) after installing halogen handles on the phenyl rings.
  • Use Pd/Cu catalysts at lower loadings with ligand-optimized systems; recover and recycle catalysts when possible.
• Tradeoffs
  • Non-chlorinated solvents may require higher temperatures or longer dissolution times; verify that optical properties and film morphology remain acceptable.
  • High-boiling green solvents can complicate drying and residual solvent removal from thin films.
• Summary table (general guidance)
  • Conventional choice: CH2Cl2, CHCl3, o-DCB → strong solubility, fast processing; higher toxicity/halogenated waste.
  • Greener alternative: toluene, anisole, 2-MeTHF, EtOAc → improved EHS profile; may need heating or slower process times.

Pharmaceutical Uses

• Not typically applicable.
  • No pharmacopeial excipient status or formulation role is indicated for this item. Due to very low aqueous solubility and lack of functional groups for ionization, it is not commonly used in pharmaceutical formulation development.
  • This product is supplied strictly for research use only (per Product Data). No clinical or therapeutic uses are stated or implied.

Physical Properties

• Item-specific specs
  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Literature/general reference values (not specifications)
  • Aggregate class: polyaryl heteroaromatic solid; expected to be non-volatile under ambient conditions.
  • Solubility profile (qualitative, literature): sparingly soluble in nonpolar alkanes; typically soluble in aromatic (toluene, xylene) and chlorinated solvents (CH2Cl2, CHCl3); negligible solubility in water.
  • Partitioning: high hydrophobicity expected due to four phenyl rings; logP expected to be high (qualitative).
  • UV–vis: conjugated chromophore; shows π–π* absorption in the near-UV with extended phenyl substitution often yielding visible fluorescence (qualitative literature note).
• Not provided for this specific item (consult CoA/Spec Sheet if needed)
  • Melting point, boiling point, density, refractive index, pKa/logP numerical values, UV cutoffs, trace impurities.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
• Interpreting common grades (general guidance)
  • Research grade: suitable for most synthetic and materials R&D. Impurity levels are controlled for general laboratory use.
  • High-purity/99%+ grade (if applicable on CoA): useful for photophysical measurements, device fabrication, or SAR studies where trace chromophores can bias spectra.
  • Metals/halogen limits, residual solvents, water/peroxide ppm: Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers/additives
  • No stabilizer information provided. If spectral or device work is intended, consider additional purification (e.g., recrystallization, Soxhlet extraction, or gradient sublimation) to remove fluorescent or redox-active micro-impurities.
• Release documentation
  • For batch-specific assay, identity confirmation (NMR/HRMS), and chromatographic purity, consult the Certificate of Analysis (CoA) accompanying your lot.

Reaction and Applications

• Typical research uses (literature/general; not product-specific claims)
  • Chromophore/scaffold in organic photophysics: furan-centered, tetraphenyl-substituted frameworks exhibit characteristic fluorescence and can serve as reference polyaryl emitters or as inert spacers in donor–acceptor systems.
  • Materials chemistry: used as a rigid, conjugated building block in small-molecule organic semiconductors and in model systems for studying charge transport and exciton migration across twisted polyaryl motifs.
  • Supramolecular chemistry: phenyl periphery supports π–π stacking and host–guest assemblies; the heteroatom center can modulate intermolecular interactions.
• Derivatization avenues expanding utility
  • Electrophilic aromatic substitution on peripheral phenyl rings (e.g., bromination/iodination) to install cross-coupling handles.
  • Cross-coupling to append electron donors/acceptors (Suzuki, Sonogashira, Stille) after prior aryl halogenation.
  • Oxidative/post-functionalization strategies on the furan core are usually disfavored due to deactivation by aryl substitution, steering reactivity to the phenyl rings.
• Practical tips
  • For spectroscopic studies, consider further purification (recrystallization/sublimation) to minimize background fluorescence from trace impurities.
  • For device fabrication, control solution aging and filter solutions (0.2 µm PTFE) prior to spin-coating to remove particulates.
• Manufacturer-provided application text: Not provided for this item.

Reaction Conditions

• General conditions reported in literature for analogous polyaryl scaffolds (illustrative guidance; not item-specific specifications)
  • Electrophilic halogenation of phenyl rings: Br2 or I2 with Lewis acid (FeBr3/AlCl3) in CH2Cl2 or CCl4 at 0–25 °C, minutes to hours; careful control to avoid polysubstitution.
  • Friedel–Crafts acylation: acyl chloride/anhydride with AlCl3 in CH2Cl2 or nitrobenzene, 0–25 °C then warm to 40–80 °C; quench cautiously to avoid hydrolysis exotherms.
  • Suzuki–Miyaura coupling (after aryl halogenation): arylboronic acid (1.2–1.5 eq), Pd(PPh3)4 (1–3 mol%), base (K2CO3/K3PO4), toluene/H2O or dioxane/H2O, 70–100 °C, 4–16 h.
  • Sonogashira coupling (iodo/bromo variants): Pd(PPh3)2Cl2 (1–2 mol%), CuI (2–5 mol%), amine base (Et3N/DIPEA), toluene or THF, 50–80 °C, 4–12 h under inert atmosphere.
  • Buchwald–Hartwig amination (after aryl halogenation): Pd2(dba)3 (1–2 mol%), ligand (e.g., XPhos/BrettPhos), NaOtBu or Cs2CO3, toluene or dioxane, 80–110 °C.
• Purification/analysis tips
  • Strong π–π interactions may cause tailing on silica; add a few percent EtOAc in hexanes or 0.1% Et3N to improve band shape. Recrystallization from toluene or chlorobenzene is often effective for polyaryls.
  • For photophysical targets, employ final polishing by sublimation where feasible.
• Yields
  • Typical yields for the above transformations on sterically hindered polyaryls range from moderate to good (40–85%) depending on substitution pattern and extent of polysubstitution.
• Always optimize on small scale and confirm conditions are compatible with your specific substitution pattern and purity goals.

Safety and Handling

• Item-specific hazard data
  • Signal word: Not specified for this item; refer to SDS.
  • H-statements: Not specified for this item; refer to SDS.
  • GHS classification and pictograms: Not specified for this item; refer to SDS.
• General laboratory guidance (literature/typical for inert polyaromatics; not product-specific)
  • Handle as a fine organic solid; avoid dust generation and inhalation. Use in a fume hood to prevent exposure to particulates.
  • Personal protective equipment: lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Wash hands after handling.
  • Incompatibilities: strong oxidizing agents (risk of combustion/oxidation). Avoid strong acids/halogenating systems if the substitution pattern is undesired.
  • Fire safety: treat as combustible organic solid; keep away from ignition sources. In case of fire, use CO2, dry chemical, or foam. Thermal decomposition may produce COx.
  • First aid (overview): move exposed personnel to fresh air; flush skin/eyes with water for at least 15 minutes; seek medical attention if irritation persists.
• Always consult the product’s SDS for authoritative, up-to-date hazard classification and response instructions.

Solvent Selection

• Compound class and polarity (literature/general)
  • Highly hydrophobic, rigid polyaromatic heterocycle; practically insoluble in water.
  • Typical good solvents: chlorinated (CH2Cl2, CHCl3), aromatic (toluene, chlorobenzene), and high-boiling polarizable media (o-dichlorobenzene) favored for spectroscopy or film casting.
• Miscibility/processing considerations
  • For thin-film fabrication (spin-coating/knife-coating), choose a solvent that balances solubility with evaporation rate to control film morphology; o-dichlorobenzene or chlorobenzene are common for slower drying.
  • For chromatography, nonpolar to mid-polar eluents (hexanes/toluene/EtOAc mixtures) are typically effective due to strong π–π interactions with silica; adding 0.1–1% triethylamine can reduce tailing of aromatic heterocycles if observed.
• Comparison (general guidance)
  • CH2Cl2: rapid evaporation, good room-temperature solubility; useful for quick spectroscopy preps.
  • Toluene: less hazardous than chlorinated solvents; higher bp supports thermal annealing of wet films.
  • o-Dichlorobenzene: very good solubility and long open time for device fabrication; higher toxicity requires careful handling.
• Note: No item-specific solubility specs are provided; verify concentration limits experimentally for your intended application.

Storage and Reconstitution

• Item-specific storage (from Product Data)
  • Storage conditions: Room temperature.
  • Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• General handling and stability (literature/typical for polyaromatic solids)
  • Store tightly closed in a dry place, protected from light to preserve photophysical properties. Desiccation is recommended if long-term storage is planned.
  • For air- and light-sensitive applications (e.g., device-grade work), consider storing under inert gas (N2/Ar) and minimizing repeated exposure.
• Reconstitution
  • No reconstitution is required for solids. To prepare solutions, use an appropriate organic solvent (e.g., CH2Cl2, toluene, chlorobenzene); warm gently and sonicate if needed to aid dissolution.
  • Filter solutions (0.2 µm PTFE) for optics or thin-film applications to remove particulates.
• Stability notes
  • Avoid strong oxidants and prolonged UV irradiation. Always refer to the CoA/SDS for any lot-specific stability or storage advisories.

Structure and Identity

• Item-specific identifiers (from Product Data)
  • CAS: 1056-77-5
  • SKU: T1029804
  • InChIKey: 93999 (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.
• Literature/computed identity details (for reference only; not specifications)
  • Common structural name: 2,3,4,5-tetraphenylfuran (tetraphenyl substitution on the furan ring)
  • Typical molecular formula (literature): C28H20O
  • Typical molecular weight (literature): ~372.46 g/mol
  • Core features: a five-membered aromatic heterocycle (furan) bearing phenyl substituents at all four alpha/beta ring carbons, creating a rigid, conjugated, polyaryl heteroaromatic system.
  • 2D description: central furan ring (O-containing) with four pendant phenyl rings; no stereocenters; overall planar-to-twisted polyaromatic topology depending on phenyl dihedral angles.
• Notes
  • The values in the first bullet are item-specific from the Product Data. Literature details are provided to aid recognition and planning; consult the product CoA/SDS for definitive identifiers used for this catalog lot.

Synthetic Utility

• Functional group landscape
  • Central furan ring (oxygen heteroaromatic) fully substituted at 2,3,4,5 with phenyl groups; absence of ring C–H on furan shifts reactivity to the peripheral phenyl rings.
  • Four phenyl rings provide multiple sites for electrophilic aromatic substitution after appropriate activation/conditions.
• Transformations (literature/general)
  • Halogenation of phenyl rings (Br2/FeBr3 or NBS/NIS under photochemical conditions when benzylic positions exist; here, focus on ring electrophilic halogenation) to enable Pd-catalyzed cross-couplings (Suzuki–Miyaura, Buchwald–Hartwig after amination, Sonogashira, Stille).
  • Friedel–Crafts acylation/alkylation on the phenyl rings under controlled stoichiometry to introduce directing groups for subsequent ortho-metalation.
  • Direct C–H activation strategies on the phenyl rings using directing groups (DG-enabled Pd/Ir/Ru catalysis) to append donor/acceptor fragments while maintaining the furan core.
  • Oxidative elaboration of the furan is generally limited by sterics/electronics; ring-opening oxidations are possible in related furans but are typically avoided when preserving the chromophore.
• Retrosynthetic value
  • Serves as a convergent node to assemble star-shaped π-systems; late-stage diversification on different phenyl rings enables library generation for SAR in materials research.
• Practical notes
  • The rigid, bulky core can slow reactions; use elevated temperature, extended times, and higher catalyst loadings for deep peripheral substitution while monitoring for overreaction.

Target Specificity

• Not applicable. This product is a small-molecule polyaromatic compound, not a biological targeting reagent. No antigen/epitope, clone, isotype, or species reactivity information applies.