Benzo[c]fluorene - ≥95% , CAS No.205-12-9

CAS: 205-12-9 Cat. No.: B1071861 Fórmula: C₁₇H₁₂ Peso molecular: 216.28 Número CE: 205-908-2 PubChem CID: 9150

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Especificações e pureza

≥95%

Condições de armazenamento de armazenamento

Room temperature

Pureza

≥95%

Nomes e identificadores

Sorrisos canónicos

C1C2=C(C3=CC=CC=C31)C4=CC=CC=C4C=C2

IUPAC Name

7H-benzo[c]fluorene

InChIKey

FRIJWEQBTIZQMD-UHFFFAOYSA-N

INCHI

1S/C17H12/c1-3-7-15-12(5-1)9-10-14-11-13-6-2-4-8-16(13)17(14)15/h1-10H,11H2

SMILES isoméricas

C1C2=C(C3=CC=CC=C31)C4=CC=CC=C4C=C2

PubChem CID

9150

Peso molecular

216.28

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Fluorenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Fluorenes
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Fluorenes
• Alternative Parents: Naphthalenes Aromatic hydrocarbons Polycyclic hydrocarbons Unsaturated hydrocarbons
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Fluorene - Naphthalene - Aromatic hydrocarbon - Polycyclic hydrocarbon - Unsaturated hydrocarbon - Hydrocarbon - Aromatic homopolycyclic compound
• Descrição: This compound belongs to the class of organic compounds known as fluorenes. These are compounds containing a fluorene moiety, which consists of two benzene rings connected through either a cyclopentane, cyclopentene, or cyclopenta-1,3-diene.
• External Descriptors: fluorenes

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

Propriedades químicas e físicas

• Peso molecular: 216.280 g/mol
• XLogP3: 5.700
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 216.094 Da
• Monoisotopic Mass: 216.094 Da
• Topological Polar Surface Area: 0.000 Ų
• Heavy Atom Count: 17
• Formal Charge: 0
• Complexity: 282.000
• 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 or immunoassay protocols are specified for this item. For materials-science applications, users typically develop project-specific protocols, for example:

• Preparing stock solutions (1–10 mg/mL) in toluene, chlorobenzene, or o-DCB with mild heating and filtration for spectroscopy or spin-coating.
• Casting or spin-coating thin films on cleaned substrates (e.g., glass/ITO/SiO2) with controlled solvent evaporation.

These are general suggestions, not validated methods for this SKU. Refer to your internal SOPs and the literature for detailed procedures.

Biological Roles

This product is intended for research use in materials science; no biological activity claims are made for the item.

General background on polycyclic aromatic hydrocarbons (PAHs) (literature context; not specific to this SKU):

• Environmental occurrence: PAHs arise from incomplete combustion and are widespread environmental contaminants; benzo-fused fluorenes are observed in combustion-derived mixtures and certain fossil materials.
• Biotransformation: Many PAHs undergo metabolic activation by cytochrome P450 monooxygenases to epoxides and dihydrodiols; subsequent conjugation (e.g., glucuronidation, sulfation) facilitates excretion. Metabolic profiles and DNA adduct formation are structure-dependent.
• Bioaccumulation: Hydrophobicity favors partitioning into lipid phases; environmental persistence is significant due to low aqueous solubility and resistance to biodegradation relative to smaller aromatics.

Use these insights only to inform environmental or toxicological research designs. For any work involving biological systems, follow institutional approvals and consult hazard assessments and the SDS.

Buffer Applications

Not typically applicable. Benzo[c]fluorene is a neutral, hydrophobic PAH with negligible water solubility and no acid–base buffering capacity. For aqueous experiments, focus instead on:

• Organic co-solvent systems (e.g., toluene-in-water emulsions with surfactants) for partitioning studies.
• Spectroscopic work in organic solvents as discussed under Solvent Selection.

Green Alternatives

While benzo[c]fluorene itself is a hydrocarbon scaffold, greener choices can often be made in its processing and derivatization.

Greener solvent/process substitutions (general guidance):

• Replace chlorinated solvents when feasible:
  • Dichloromethane/chloroform → 2-methyltetrahydrofuran (2-MeTHF), cyclopentyl methyl ether (CPME), anisole, or dimethyl carbonate (DMC) for dissolutions and certain couplings, acknowledging solubility trade-offs for PAHs.
• Higher-boiling aromatics with better profiles:
  • Chlorobenzene/o-DCB → anisole or mesitylene in cases where similar solubility is achievable and photophysics permit.
• Oxidative cyclizations:
  • Classical FeCl3/DDQ systems → electrochemical oxidative coupling or hypervalent iodine reagents with recyclable electrolytes/mediators (emerging literature).

Small comparison (typical considerations):

• DCM vs. 2-MeTHF: 2-MeTHF offers bio-based origin and lower toxicity but may reduce solubility; heating and seeding can compensate.
• Chlorobenzene vs. anisole: Anisole is less hazardous and sometimes suitable for film formation; evaporation rates differ, affecting morphology.

Operational levers:

• Minimize solvent volumes via concentrated processing and hot filtration.
• Recycle high-boiling solvents by distillation.
• Favor catalytic, atom-economical cross-couplings (Suzuki with aqueous workup) over stoichiometric organometallics when route allows.

Note: Validate green substitutions at small scale; PAH solubility and film properties are sensitive to solvent polarity and evaporation kinetics.

Pharmaceutical Uses

No excipient or pharmacopeial roles are specified for this item. As a hydrophobic PAH, benzo[c]fluorene is not commonly employed in pharmaceutical formulations.

Relevant research-only contexts (general):

• Analytical/toxicological standards: May be used as a reference compound in PAH analytical method development (GC–MS/LC–MS) and environmental monitoring validation.
• Photophysical probes in fundamental research: As part of model systems for studying π–π interactions and excited-state behavior (non-clinical, lab-scale).

No medical or clinical use is implied or permitted; for research use only.

Physical Properties

Item-specific numerical specifications (bp, mp, density, UV cutoff, water/metal/peroxide content) are not provided for this product. Refer to the CoA/Spec Sheet for definitive values.

General/literature characteristics (for context; not item-specific specs):

• Aggregated physical profile: Polycyclic aromatic hydrocarbon, typically isolated as crystalline solid with high thermal stability relative to lower PAHs.
• Phase behavior: High melting point solid; boiling point often not practically observed due to thermal decomposition—purification typically by recrystallization or sublimation (literature, PAH class behavior).
• Solubility: Very low in water; soluble in nonpolar and moderately polar organic solvents (e.g., toluene, chlorobenzene, dichloromethane, THF, o-dichlorobenzene) — solubility generally increases with temperature (literature, PAH class behavior).
• Partitioning: Expected high hydrophobicity (high logP) consistent with PAHs of similar ring count (literature trend).
• Optical: Extended π-conjugation supports UV–vis absorption in the near-UV/visible onset and characteristic fluorescence; exact λmax/onset depend on substitution, solvent, and purity (literature).

Notes for use:

• For thin-film or spectroscopy work, hot solutions in high-boiling aromatics (chlorobenzene, o-DCB) often give best solubility; filter hot through 0.2 µm PTFE to remove particulates.
• Avoid quoting literature numbers as product specifications; verify on the supplied CoA.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers/additives: Not specified for this item; refer to CoA/Spec Sheet.

Interpretation and general guidance:

• Research-grade PAHs are commonly supplied at high chemical purity for materials science, spectroscopy, and device fabrication. Relevant quality dimensions include:
  • Chemical purity (HPLC/GC): Minimizes background fluorescence/absorbance and electronic trap states in devices.
  • Isomeric purity: Critical for reproducibility in photophysics and charge transport; benzo[a]/[b]/[c]fluorene isomer cross-contamination can shift spectra and film morphology.
  • Residual metals: Important when used in optoelectronics; transition metals can quench emission and alter conductivity. If metals are critical, request ICP data.
  • Particle size and polymorph: Affects thin-film formation and solution processing; pre-grinding or controlled recrystallization may improve film uniformity.
• If your application is sensitive (e.g., OLED emissive layer, single-molecule spectroscopy), consider:
  • Requesting recent CoA including HPLC trace, water content (Karl Fischer), and UV–vis baseline.
  • Performing an in-house recrystallization/sublimation and verifying via NMR/HRMS and elemental analysis.
• UV-cutoff and fluorescence background for solvents used with this material should be selected to match your analytical method; the grade of the solvent can dominate background signals.

Reaction and Applications

Materials science use cases (category-relevant):

• Photophysics and optoelectronics: The extended, rigid π-system of benzo[c]fluorene is valuable as a model PAH for studying exciton dynamics, fluorescence, and intersystem crossing, and as a structural motif in organic semiconductors (OLEDs, OPVs, OFETs) when incorporated into larger architectures (literature context).
• Nanographene and carbon-rich materials: Serves as a precursor or subunit in bottom-up syntheses of larger nanographenes/graphitic ribbons via Scholl-type oxidative cyclodehydrogenations and aryl–aryl coupling strategies.

Common synthetic transformations on the benzo[c]fluorene core (general literature):

• Electrophilic aromatic substitution (EAS): Controlled halogenation or Friedel–Crafts acylation/alkylation at activated ring positions; regioselectivity influenced by the “bay” and “peri” regions.
• Directed metalation/C–H activation: Lithiation (s-BuLi/t-BuOK or TMP-bases) or transition-metal-catalyzed C–H functionalization to install boron, silyl, or halide handles.
• Cross-coupling: After aryl halide or boronate installation, use Suzuki–Miyaura, Stille, Negishi, or Kumada couplings to elaborate donor–acceptor structures.
• Oxidative fusion (Scholl reaction): FeCl3, DDQ/TfOH, or AlCl3-promoted ring closures to extend conjugation.

Practical tips:

• Solubility limits handling; perform reactions in high-boiling aromatics or chlorinated solvents and consider phase-transfer or surfactant media for aqueous workups.
• Protect from over-oxidation during late-stage functionalization; monitor by TLC/UPLC and verify isomeric purity by 2D NMR.
• For device applications, post-synthesis purification by gradient sublimation can markedly improve performance metrics.

Reaction Conditions

General literature guidance for functionalizing benzo-fused fluorenes (illustrative; not item-specific specs):

• Electrophilic halogenation:

  • Conditions: NBS (1.0–1.2 eq) in DMF or CHCl3, 0–25 C, 1–6 h; monitor by TLC/HPLC.
  • Outcome: Monobromination at activated aromatic positions; regioselectivity depends on solvent and temperature.

• C–H borylation (Ir-catalyzed):

  • Catalyst: [Ir(COD)OMe]2 (1–2 mol%) with dtbpy (4–8 mol%).
  • Reagents/solvent: B2pin2 (1.5–2.5 eq), cyclohexane or octane, 80–120 C, 6–18 h under N2.
  • Use: Access to boronate esters for Suzuki couplings.

• Suzuki–Miyaura coupling:

  • Reagents: Aryl boronate (1.2–1.5 eq) with aryl halide of benzo[c]fluorene (or vice versa), Pd(PPh3)4 (1–3 mol%) or Pd-PEPPSI, K2CO3/K3PO4 base, toluene/EtOH/H2O (biphasic) or dioxane/H2O, 80–110 C, 4–18 h.
  • Notes: Degas solvents; employ high-boiling media if solubility is limiting.

• Scholl cyclodehydrogenation:

  • Conditions: FeCl3 (4–10 eq) in nitromethane or DCM/MeNO2, 0–25 C to reflux, 2–24 h; or DDQ (2–6 eq) with catalytic TfOH in DCM, 0–25 C.
  • Considerations: Control overoxidation and chlorination; purify by silica gel pretreated with base or by sublimation.

• Purification:

  • Recrystallization from toluene/xylene or gradient sublimation (200–350 C under high vacuum, as thermal stability permits).

Adjust conditions to substrate substitution patterns. Verify identity and purity via 1H/13C NMR (aromatic region diagnostics), HRMS, and, for materials work, UV–vis/PL and elemental analysis.

Safety and Handling

Safety classifications (GHS, signal word, H-statements, pictograms) are not specified for this item; consult the product SDS for authoritative safety information.

General PAH-focused handling guidance (not item-specific classification):

• Hazards: Polycyclic aromatic hydrocarbons can display environmental persistence and, in some cases, mutagenic or carcinogenic potential upon metabolic activation. Treat unknown PAHs conservatively—avoid inhalation, ingestion, and skin contact.
• Personal protective equipment (PPE): Use appropriate lab coat, safety glasses or goggles, and chemically resistant gloves (e.g., nitrile). Handle powders in a fume hood to minimize dust inhalation.
• Incompatibilities: Strong oxidizers (risk of exothermic reaction); avoid flames/ignition sources when using hot, high-boiling organic solvents for dissolution.
• Hygiene measures: Wash hands thoroughly after handling; avoid contamination of common areas. Prevent release to the environment; manage waste as hazardous organic.
• First aid (general):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin: Wash with soap and water; remove contaminated clothing.
  • Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present and easy to do.
  • Ingestion: Rinse mouth; seek medical advice. Do not induce vomiting unless directed by medical personnel.
• Fire safety: Use CO2, dry chemical, or foam on solvent fires. Many PAHs are combustible; avoid dust accumulation.
• Always defer to and follow the SDS for this specific SKU.

Solvent Selection

Benzo[c]fluorene is a hydrophobic, neutral PAH. Solvent choice is driven by solubility, thermal budget, and intended application (spectroscopy vs. film formation).

• Polarity/miscibility profile (general):

  • Water: Essentially insoluble.
  • Good solvents: Aromatics (toluene, chlorobenzene, o-dichlorobenzene), chlorinated solvents (dichloromethane, chloroform), and some ethers (THF, CPME) at elevated temperature (literature trends for PAHs).
  • Poor solvents: Very polar protic media (water, MeOH, EtOH) and alkanes at ambient temperature.

• Practical recommendations:

  • Spectroscopy: Use spectrophotometric-grade toluene, cyclohexane, or dichloromethane. Filter through 0.2 µm PTFE to remove particulates.
  • Thin films/spin coating: Chlorobenzene or o-DCB provide higher solubility and slower evaporation for uniform films; control concentration (typically 1–10 mg/mL) and temperature.
  • Crystallization: Toluene, xylenes, or chlorobenzene; hot filtration improves crystal quality.

• Comparison (general guidance):

  • Toluene (bp 111 C) balances solubility and volatility—good for solution studies.
  • Chlorobenzene (bp 132 C) and o-DCB (bp 180 C) enable higher-temperature processing and greater solubility.
  • DCM (bp 40 C) enables rapid film deposition but may limit solubility.

Always confirm solvent compatibility with your downstream process and analytical method. For trace analysis, ensure low background fluorescence and minimal peroxide content in etheral solvents.

Storage and Reconstitution

• Storage conditions (item-specific): Room temperature (as provided). Store tightly closed in a dry place, away from direct light and strong oxidizers.
• Shipping: Not specified for this item; refer to CoA/Spec Sheet.

Reconstitution and handling (general guidance):

• Solubility: Poorly soluble in water; dissolve in suitable organic solvents (toluene, chlorobenzene, o-DCB, DCM, THF). Warm gently (40–120 C depending on solvent) with stirring/sonication to aid dissolution.
• Filtration: For spectroscopy or thin films, hot-filter through 0.2 µm PTFE to remove particulates.
• Stock solutions: Prepare fresh where possible; for short-term storage, keep in amber vials under inert gas to minimize adventitious oxidation/contamination.
• Freeze–thaw: Not typically applicable to solids; if solutions are stored, avoid repeated freeze–thaw by aliquoting.

Always consult the product’s SDS and CoA for any additional, lot-specific instructions.

Structure and Identity

Benzo[c]fluorene is a polycyclic aromatic hydrocarbon (PAH) belonging to the benzo-fused fluorene isomer family, valued in materials research for its extended π-system and rigid, planar framework.

• Item-specific identifiers (from Product Data)

  • SKU: B1071861
  • Product name: Benzo[c]fluorene
  • CAS: 205-12-9
  • PubChem CID: 9150
  • InChIKey: 90193 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed identifiers (general reference; not item-specific specs)

  • Typical molecular formula: C17H12 (literature)
  • Typical molecular weight: ~216.28 g/mol (literature)

• Structural features (general chemistry description)

  • Framework: Four fused aromatic rings derived from fluorene with an additional benzene ring fused at the “c” face.
  • Functional groups: Hydrocarbon only; no heteroatoms; fully aromatic π-system with peri- and bay-regions characteristic of benzo-fused fluorenes.
  • Stereochemistry: None (achiral, planar PAH).
  • 2D description: A fluorene core (two benzene rings bridged by a five-membered ring) further fused with an additional benzene ring to create a contiguous, nearly planar, rigid polycyclic scaffold with extended conjugation suitable for optoelectronic studies.

Synthetic Utility

Benzo[c]fluorene is a valuable building block for constructing larger π-extended, rigid aromatic systems and donor–acceptor frameworks.

Key reactivity elements (general literature):

• Polycyclic aromatic core: Amenable to regioselective functionalization at “bay” or “peri” positions via EAS or metalation strategies, enabling diversification without disrupting planarity.
• Handle installation:
  • Halogenation (NBS/NCS or electrophilic Br2/Cl2 under controlled conditions) for subsequent cross-coupling.
  • Borylation (Ir- or Ni-catalyzed C–H borylation) to access pinacol boronate esters for Suzuki couplings.
• π-Extension strategies:
  • Suzuki–Miyaura or Stille couplings to append aryl/heteroaryl units.
  • Scholl-type oxidative cyclodehydrogenation to “fuse” appended rings, generating nanographenes/PAH ribbons.
• Redox and substitution chemistry: Oxidation to fluorenone-type motifs requires caution (different isomeric cores); selective transformations can tune HOMO–LUMO gaps and fluorescence.

Retrosynthetic value:

• Serves as a compact, conformationally constrained donor unit that can be merged with acceptors (e.g., benzothiadiazole, diketopyrrolopyrrole) to yield D–A systems with balanced solubility/rigidity for OPV/OLED/OFET research.

Target Specificity

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

Perguntas frequentes

What is the purity of this product?

This product is supplied at ≥95% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 205-12-9, the molecular formula is C17H12, and the molecular weight is 216.28 g/mol. InChIKey FRIJWEQBTIZQMD-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.