This compound belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings.
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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.
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Application Protocols
No validated biological assay protocols are provided in the Product Data. As a small-molecule fluorophore/monomer, typical usage is in synthetic transformations, materials preparation, and spectroscopic studies.
General guidance (literature, non-validated by manufacturer):
Fluorescence stock solutions: prepare 1–10 mM stocks in spectroscopic-grade toluene or CH2Cl2 under low light; filter (0.2 µm PTFE) to remove particulates; store in amber vials under N2 at 2–8 °C for short term.
Thin-film preparation: dissolve with polymer matrix in CHCl3 or toluene; spin-coat or drop-cast; dry in the dark under inert gas to minimize photooxidation.
Copolymerization: combine with comonomers and AIBN in toluene; degas via freeze–pump–thaw or N2 sparge; polymerize at 65–80 °C; precipitate into methanol; dry under vacuum.
These are non-specific, literature-style suggestions. For application-specific procedures, consult relevant peer-reviewed sources and optimize to your equipment and safety protocols.
Biological Roles
Item is supplied for research use only. No biological role is specified in the Product Data.
General/literature context for anthracene derivatives:
Natural occurrence/role: 2-vinylanthracene is not a natural metabolite and has no known physiological role.
Biophysical utility: anthracene fluorophores are often used as hydrophobic probes in micelles, membranes, polymer matrices, and host–guest assemblies due to their environment-sensitive fluorescence and propensity for excimer formation.
Interactions: polycyclic aromatic systems can engage in π–π stacking with aromatic residues and nucleobases in vitro; such interactions are exploited in materials and supramolecular chemistry studies, not as a biological function.
Stability in biological media: poor aqueous solubility and strong adsorption to hydrophobic surfaces limit direct use in aqueous biology without formulation (e.g., cyclodextrin inclusion complexes, micellar carriers, or organic cosolvents) — approach with caution and validate compatibility.
No claims are made regarding pharmacology, toxicity thresholds, or clinical relevance. For any biological assay development, pre-validate solvent systems (e.g., DMSO stock diluted into buffered media well below solvent cytotoxicity limits) and confirm that spectral properties are not confounded by medium components (protein binding, inner filter effects).
Buffer Applications
This compound is a hydrophobic, water-insoluble PAH and is not typically used to prepare aqueous buffers or classical buffering systems.
Practical notes (if used in aqueous settings):
Delivery into buffers generally requires a cosolvent (e.g., DMSO, MeCN) or a carrier system (cyclodextrins, micelles, liposomes). Keep final organic cosolvent below 1–2% v/v to minimize impacts on biological systems.
Verify that the buffer components do not strongly quench or inner-filter the anthracene fluorescence (phosphate and Tris are typically compatible; high ionic strength and aromatic additives may affect spectra).
Filter solutions through low-binding PTFE/PP to limit losses from adsorption.
For pH control, ionic strength adjustment, or electrophoresis, select conventional buffer components (phosphate, Tris, HEPES, MES). 2-Vinylanthracene itself does not contribute buffering capacity.
Green Alternatives
While 2-vinylanthracene itself is the target substrate/monomer, greener choices largely pertain to solvent and reagent selection during its use and transformation.
Greener solvent options (literature/general):
Toluene vs. benzene
Toluene offers similar solubilizing power for PAHs but with a better toxicological profile than benzene.
2-MeTHF or CPME vs. THF/diethyl ether
Bio-based 2-MeTHF and low-peroxide CPME provide improved safety (lower peroxide formation, higher bp) and reduced environmental impact.
Ethyl acetate or dimethyl carbonate vs. dichloromethane
Where reaction scope allows, switch to non-chlorinated solvents to reduce halogenated waste.
Illustrative comparison (general):
DCM: excellent solubility and fast evaporation; environmental and health concerns; difficult to replace for some room-temperature electrophilic additions.
2-MeTHF: good for hydroboration and organometallic steps; water-tolerant biphasic workups; renewable feedstock; may solubilize PAHs slightly less than aromatics.
Toluene: robust for thermal/radical steps and spectroscopy; moderate EHS profile among aromatics.
Reagent and process considerations:
Use catalytic oxidations (e.g., O2 with organocatalysts or TEMPO systems) instead of stoichiometric peracids where feasible for vinyl oxidations.
Favor flow ozonolysis with on-demand ozone generation and immediate quench to enhance safety when cleaving the vinyl group.
Reduce light/oxygen exposure to extend reagent life and minimize degradants, reducing rework and waste.
Pharmaceutical Uses
No pharmacopeial grade, excipient role, or formulation specification is provided in the Product Data, and this material is offered for research use only.
General, non-clinical context:
Role in R&D: anthracene-containing fluorophores like 2-vinylanthracene may be employed as research tracers in formulation development, polymer matrix characterization, or to monitor diffusion/partitioning in non-aqueous systems due to their strong fluorescence.
Compatibility: limited aqueous solubility precludes direct use in typical aqueous drug formulations; any exploratory use would require appropriate non-aqueous vehicles or solid dispersion systems and is strictly for laboratory investigation.
Regulatory status: no USP/Ph. Eur. monograph known for 2-vinylanthracene (literature/general). Any GMP-related usage would demand extensive qualification and impurity profiling beyond typical research grades.
No therapeutic or clinical claims are made. For any handling within a pharmaceutical research environment, ensure documented impurity control (e.g., PAH-related impurities), photostability studies, and alignment with internal safety assessments.
Physical Properties
Item-specific specifications for this lot are not provided in the Product Data. Refer to the CoA/Spec Sheet for definitive values.
Appearance (Product Data): Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet. (Literature: C16H12)
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet. (Literature: 204.27 g/mol)
Literature/general properties (for guidance only; not item specifications):
Phase at RT: solid PAH; typically crystalline.
Solubility: practically insoluble in water; soluble in nonpolar and moderately polar organic solvents such as toluene, dichloromethane, chloroform, THF, benzene, and DMF; sparingly soluble in alcohols (general PAH behavior).
Photophysical behavior: strong π–π* absorption in the near-UV; blue fluorescence with emission typically in the 400–480 nm range depending on solvent polarity and microenvironment (literature, general for vinyl-anthracenes).
Partitioning: expected high hydrophobicity (logP > 3, literature trend for anthracenes), leading to strong affinity for organic phases and sorbents.
Thermal behavior: stable under ambient conditions when protected from intense light and oxidants; vinyl group may polymerize/radically add under initiating conditions.
Do not treat the above literature values as specifications for this item. Always verify numerical properties against the CoA for the shipped lot.
Quality and Grades
Grade/Purity (Product Data): Not specified for this item; refer to CoA/Spec Sheet.
Guidance on typical quality considerations for 2-vinyl PAHs (general):
Purity assessment: For photophysical work or polymerization studies, high chemical purity and low fluorescent impurities are important. Verify by 1H/13C NMR, HPLC/UPLC, and GC (if applicable). Anthracene-derived impurities can strongly affect emission spectra.
UV-Vis/HPLC grade solvents: When using this compound as a fluorophore or reference emitter, pair it with low-UV-absorbance solvents (HPLC/UV-Vis grade) to minimize baseline noise.
Stabilizers: Some vinyl aromatics are supplied with trace polymerization inhibitors (e.g., MEHQ, BHT). This item’s stabilizer status is not provided; check the CoA. Presence of inhibitors can impact radical polymerization kinetics and should be removed when necessary (e.g., basic alumina short plug, if compatible).
Metals/ionic contaminants: Not specified for this item; refer to CoA/Spec Sheet. For cross-coupling or photoredox studies, low-halide and low-metal backgrounds help achieve reproducibility.
Water/peroxide levels: Not specified for this item; refer to CoA/Spec Sheet. While the solid itself is not hygroscopic, residual moisture in solvents used with it can alter photophysics and reactivity; dry solvents are recommended for sensitive transformations.
Reaction and Applications
2-Vinylanthracene combines an activated polyaromatic chromophore with a terminal alkene, enabling a broad reaction manifold and photophysical uses.
Synthesis/derivatization (literature, general):
Electrophilic additions to the vinyl group: halogenation, hydrohalogenation (Markovnikov/anti-Markovnikov depending on conditions), and acid-catalyzed additions while typically preserving the anthracene core.
Oxidations/cleavages: ozonolysis or Lemieux–Johnson oxidative cleavage affords 2-anthracenecarboxaldehyde or 2-anthracenecarboxylic acid derivatives, valuable intermediates.
Hydroboration–oxidation: anti-Markovnikov hydration yields 2-(2-hydroxyethyl)anthracene; hydroboration followed by cross-coupling can elaborate the side chain.
Epoxidation/dihydroxylation: forms epoxide/1,2-diol derivatives for further functionalization.
Radical polymerization/copolymerization: the vinyl group participates in free-radical polymerization, producing anthracene-containing polymers for optoelectronic and sensing applications.
Heck-type arylation: extension of conjugation via coupling of the terminal alkene with aryl/vinyl halides under Pd catalysis (literature precedents for styrenyl arenes).
Applications (literature, general):
Fluorescent probe/standard: strong blue emission; used to study microenvironment polarity, polymerization progress, and supramolecular hosts via fluorescence changes.
Organic electronics/photonic materials: building block for emissive polymers and OLED model systems due to rigid PAH core.
Photochemical studies: anthracenes are models for triplet–singlet dynamics, excimer/exciplex formation, and photooxygenation; vinyl substitution tunes spectra and reactivity.
Practical notes:
Minimize light/oxygen during photophysical experiments to avoid photooxidation (e.g., purge with N2/Ar, use amberware).
For radical chemistry, remove inhibitors if present and use freshly distilled/peroxide-free solvents.
Reaction Conditions
General literature-guided conditions for common transformations of 2-vinylanthracene (provided as guidance; optimize per substrate and scale):
Reagents: mCPBA (1.1–1.5 equiv) in CH2Cl2 at 0–25 °C.
Alternatives: in situ peracids from H2O2/acetic acid with phase-transfer catalysts.
Notes: monitor to avoid over-oxidation of the anthracene core; light protection recommended.
Ozonolysis to carbonyl derivatives
Solvent: CH2Cl2 or MeOH/CH2Cl2 at −78 to −30 °C; ozone to faint blue, then reductive (Me2S, PPh3) or oxidative (H2O2) workup.
Outcome: 2-anthracenecarboxaldehyde/acids depending on workup.
Heck coupling (vinyl arylation/extension)
Catalyst: Pd(OAc)2/P(o-tol)3 or Pd2(dba)3/PPh3; base: Et3N or K2CO3.
Solvent: DMF, NMP, or toluene; 80–140 °C.
Notes: sterics of the anthracene ring can influence regioselectivity and E/Z of the new alkene.
Radical polymerization/copolymerization
Initiators: AIBN, benzoyl peroxide (0.5–2 mol%).
Solvent/bulk: toluene or bulk; 60–110 °C depending on initiator half-life.
Notes: remove inhibitors if present; control O2; consider RAFT/ATRP mediators for dispersity control.
Yields and exact conditions vary; consult primary literature for precise protocols relevant to your substrate set.
Safety and Handling
GHS classification and specific hazards are not provided in the Product Data. Always consult the product SDS for authoritative safety information.
Product Data (hazard fields):
Signal Word: Not specified for this item; refer to SDS.
H-Statements: Not specified for this item; refer to SDS.
GHS Classification/Pictograms: Not specified for this item; refer to SDS.
General laboratory safety considerations for polycyclic aromatic hydrocarbons and vinyl aromatics (literature/general):
Hazards: combustible organic solid; may cause irritation to skin, eyes, and respiratory tract. Many PAHs are harmful to aquatic life with long-lasting effects; handle to minimize environmental release.
Light sensitivity: extended aromatics can undergo photooxidation; protect from strong UV/visible light during handling and storage.
Incompatibilities: strong oxidizing agents (risk of exothermic reaction/oxidation); radical initiators and peroxides (can trigger unwanted polymerization at the vinyl group).
Engineering controls: handle in a fume hood to avoid dust and vapor exposure during solvent handling.
PPE: lab coat, safety glasses or goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Avoid skin contact; wash thoroughly after handling.
First aid (overview; defer to SDS):
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: rinse with water for several minutes; remove contaminated clothing; seek medical advice if irritation persists.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Waste: collect as halogen-free organic waste unless solvent system dictates otherwise; prevent release to drains.
Solvent Selection
As a hydrophobic PAH, 2-vinylanthracene dissolves best in nonpolar and moderately polar organic solvents. Choice depends on application (spectroscopy vs. synthesis vs. polymerization).
Polarity/miscibility profile (general):
Water: effectively insoluble.
Nonpolar aromatics (toluene, xylenes): excellent solubility; good for radical reactions and high-temperature chemistry.
Chlorinated solvents (CH2Cl2, CHCl3): good solubility at room temperature; ideal for chromatography and many electrophilic additions.
Ethers (THF, CPME): moderate-to-good solubility; suitable for hydroboration–oxidation and organometallic additions under anhydrous conditions.
Polar aprotics (DMF, DMSO, MeCN): varying solubility; may be used for cross-couplings/photoredox but can quench fluorescence.
Small comparison (general guidance):
Toluene: high solubility, high bp; excellent for thermal radical polymerization but slower evaporation.
Dichloromethane: rapid dissolution/evaporation; good for room-temperature reactions and thin-film casting; avoid for base-sensitive steps.
THF/2-MeTHF: enable organometallic and hydroboration chemistry; 2-MeTHF offers greener profile.
Acetonitrile: supports photoredox/electrochemistry; may diminish fluorescence quantum yield compared to nonpolar solvents.
Practical tips:
For fluorescence measurements, use spectroscopic-grade toluene or cyclohexane to maximize quantum yield and resolve vibronic structure.
For ozonolysis or dihydroxylation of the vinyl group, CH2Cl2 or MeOH/CH2Cl2 mixtures are common (literature, general).
Shipped In (Product Data): Not specified for this item; refer to CoA/Spec Sheet.
Best practices (general):
Protect from light: store in amber glass, tightly sealed, to minimize photooxidation and unintended photochemistry of the anthracene core.
Atmosphere: store under inert gas (N2/Ar) if possible, especially for long-term storage, to limit slow oxidative degradation.
Dry conditions: keep container tightly closed in a dry place; avoid prolonged exposure to humid air.
Reconstitution/solution preparation (general):
Solvents: toluene, dichloromethane, chloroform, THF, or DMF typically dissolve the compound readily. Water is not recommended due to negligible solubility.
Concentration ranges: 1–10 mM for spectroscopic stocks; 1–50 mg/mL for synthetic use, depending on solvent and application.
Filtration: use PTFE syringe filters (0.2–0.45 µm) for particle removal prior to spectroscopy or thin-film preparation.
Stability of solutions: stable for days to weeks at 2–8 °C in the dark under inert gas; monitor for changes in absorption/fluorescence indicating degradation. Prepare fresh for sensitive experiments.
Always refer to the CoA/SDS for any item-specific storage or stabilizer information and observe the "For research use only" notice.
Structure and Identity
2-Vinylanthracene is a polycyclic aromatic hydrocarbon (PAH) bearing a vinyl substituent on the anthracene core at the 2-position, extending the conjugation and imparting strong fluorescence.
Item-specific identifiers (Product Data)
CAS: 2026-16-6
CID: 4413601
InChIKey: 173138 (as provided)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature identifiers and composition (for reference)
Molecular formula (literature): C16H12
Molecular weight (literature): 204.27 g/mol
Structural features
Anthracene framework: three linearly fused benzene rings (planar, fully aromatic).
Substituent: a vinyl group (–CH=CH2) at C2 of the anthracene, conjugated to the polyaromatic system.
Functional groups: aromatic rings; terminal alkene (vinyl) capable of electrophilic addition, radical polymerization, and oxidative transformations.
Stereochemistry: none at the vinyl carbon (E/Z not applicable to a terminal vinyl substituent); overall achiral.
2D structure described in words
The molecule consists of an anthracene tricyclic aromatic backbone. At the 2-position (peri-adjacent to the central ring fusion), a two-carbon ethenyl chain extends from the ring, terminating in a vinyl CH2. The extended conjugation from the vinyl into the anthracene π-system enhances absorbance in the near-UV and blue fluorescence (literature, general).
Synthetic Utility
2-Vinylanthracene is a versatile intermediate that merges a reactive terminal alkene with a rigid, conjugated PAH scaffold.
Key functional elements and reactivity (literature, general):
Terminal alkene (vinyl):
Supports electrophilic additions (HX, X2), radical additions (thiol–ene), and polymerization.
Hydroboration enables anti-Markovnikov hydration and avenues to C–B intermediates for further coupling after derivatization.
Epoxidation and syn-dihydroxylation provide handles for nucleophilic opening and diversification.
Anthracene core:
Photodimerization and [4+4] cycloadditions (on unsubstituted positions) under UV; substitution pattern in 2-position modulates photoreactivity.
Electrophilic substitution at remaining ring positions for further derivatization (nitration, bromination under controlled conditions).
Retrosynthetic value:
Serves as a convergent branch point to 2-substituted anthracenes via vinyl-to-carbonyl interconversions, chain extensions (Heck, hydroformylation), or functional group interconversions.
As a monomer unit, introduces a fluorescent, rigid side chain into radical or controlled radical polymerizations (RAFT/ATRP when appropriately formulated) for emissive materials and sensors.
Practical considerations:
Protect from strong light/oxygen when targeting photophysical purity.
If polymerization inhibitors are present, pre-purify on basic alumina (compatibility permitting) before radical reactions.
Choose solvent to balance reactivity and photophysics: toluene for high-temperature steps, CH2Cl2 for room-temperature electrophilic additions, 2-MeTHF for greener organometallic operations.
Target Specificity
Not applicable. This product is a small-molecule PAH, not an antibody or biological targeting reagent. No antigen, epitope, species reactivity, clone, or isotype information applies.
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