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Acenaphthene is a polycyclic aromatic hydrocarbon containing a compact, fused-ring molecular structure.
Acenaphthene serves as an important intermediate in the manufacture of dyes, pigments, resins, agrochemical intermediates, and specialty aromatic derivatives.
Acenaphthene is generally available as a white to pale-yellow crystalline solid with very low water solubility and good compatibility with suitable organic solvents.
CAS Number: 83-32-9
EC Number: 201-469-6
Molecular Formula: C12H10
Molecular Weight: 154.21 g/mol
SYNONYMS
1,2-Dihydroacenaphthylene, Acenaphthylene, 1,2-dihydro-, 1,2-Dihydro-acenaphthylene, 1,2-Dihydroacenaphthene, 1,8-Dihydroacenaphthene, 1,8-Ethylenenaphthalene, 1,2-Ethylenenaphthalene, Peri-Ethylenenaphthalene, peri-Ethylenenaphthalene, Naphthyleneethylene, Ethylenenaphthalene, Acenaphtene, Acenaphthen, Acenaphten, Acenaphthène, Acenafteno, Acenaften, Acenaftene, Acenaphthenum, Acenaphthene Hydrocarbon, Acenaphthene PAH, C12H10, CAS 83-32-9, EC 201-469-6, EINECS 201-469-6, NSC 7657, UN 3077
APPLICATIONS
Acenaphthene serves as an important aromatic intermediate in the production of dyes requiring a rigid and highly conjugated carbon framework.
Acenaphthene supports controlled oxidation and substitution reactions that allow manufacturers to prepare more complex color-forming compounds.
Acenaphthene functions as a principal starting material for the preparation of acenaphthenequinone, a reactive intermediate used in numerous downstream synthesis routes.
Acenaphthene facilitates the formation of acenaphthenequinone through controlled oxidation of the ethylene-bridged aromatic structure.
Acenaphthene contributes to the manufacture of anthraquinone-related dye intermediates by providing a compact fused-ring building block.
Acenaphthene enables subsequent condensation and ring-extension reactions that generate larger conjugated systems with useful color characteristics.
Acenaphthene finds application in pigment-intermediate synthesis where molecular rigidity can support color strength, thermal performance, and chemical durability.
Acenaphthene allows pigment manufacturers to modify shade and compatibility through oxidation, nitration, halogenation, and other functionalization processes.
Acenaphthene supports the production of vat-dye intermediates that are transformed through multistep reactions into colorants for selected textile applications.
Acenaphthene provides a stable aromatic nucleus that can be adapted to obtain the required reduction behavior, shade, and fiber affinity.
Acenaphthene enhances the preparation of disperse-dye intermediates intended for hydrophobic synthetic materials.
Acenaphthene contributes a nonpolar fused-ring structure that can be chemically modified to improve compatibility with polyester and similar substrates.
Acenaphthene facilitates the development of solvent-soluble colorants for plastics, coatings, printing inks, and specialty resin systems.
Acenaphthene enables chemists to introduce suitable functional groups that adjust organic-solvent compatibility and color performance.
Acenaphthene offers a useful raw material for producing aromatic pigment precursors employed in coating and printing applications.
Acenaphthene supports the preparation of derivatives capable of providing strong visible absorption and resistance to demanding processing conditions.
Acenaphthene serves as a building block in the synthesis of specialty resins and resin intermediates containing fused aromatic structures.
Acenaphthene promotes structural rigidity when suitable derivatives are incorporated into thermosetting or thermoplastic material systems.
Acenaphthene contributes to alkyd-resin and polyester-related research by providing an aromatic intermediate that can be oxidized into multifunctional derivatives.
Acenaphthene enables the preparation of oxygen-containing compounds that participate in resin modification and polymer-development processes.
Acenaphthene supports the manufacture of specialty polymer additives when converted into derivatives with suitable thermal and compatibility characteristics.
Acenaphthene allows formulators to tailor molecular polarity, solubility, and interaction with selected polymer matrices.
Acenaphthene finds application in the preparation of heat-resistant aromatic compounds for advanced polymer and materials research.
Acenaphthene provides a compact carbon-rich structure that can contribute to rigidity and thermal stability after appropriate chemical transformation.
Acenaphthene functions as an intermediate in selected agrochemical synthesis routes involving nitration, oxidation, halogenation, or condensation.
Acenaphthene enables the production of substituted aromatic compounds that may undergo further conversion into crop-protection intermediates.
Acenaphthene supports the development of insecticide intermediates when the acenaphthene framework is transformed into the required functional derivative.
Acenaphthene provides several reactive positions for introducing groups that influence biological activity and formulation compatibility.
Acenaphthene contributes to fungicide-intermediate research by serving as a starting structure for substituted fused-ring compounds.
Acenaphthene facilitates systematic modification of aromatic substitution patterns during the development of specialty active-material precursors.
Acenaphthene enables the preparation of pharmaceutical research intermediates in synthesis programs that require a rigid polycyclic aromatic scaffold.
Acenaphthene offers a defined molecular framework for investigating how fused-ring structures influence chemical and physical behavior.
Acenaphthene serves as a starting material for acenaphthenequinone derivatives employed in organic synthesis and functional-material research.
Acenaphthene supports the production of quinone-based compounds with modified electronic, optical, and coordination properties.
Acenaphthene promotes the synthesis of imides, diimines, and related nitrogen-containing compounds through reactions involving oxidized acenaphthene derivatives.
Acenaphthene provides access to functional molecules used in coordination chemistry, catalyst research, and advanced organic synthesis.
Acenaphthene facilitates the manufacture of ligands when acenaphthenequinone is condensed with suitable nitrogen-containing reactants.
Acenaphthene thereby supports the development of metal-complex systems designed for catalytic and molecular-structure investigations.
Acenaphthene contributes to catalyst-development research through the preparation of rigid diimine and related ligand frameworks.
Acenaphthene enables controlled modification of ligand steric and electronic properties through substitution of the fused aromatic structure.
Acenaphthene finds application as a reference compound in environmental testing for polycyclic aromatic hydrocarbons.
Acenaphthene allows laboratories to develop and validate analytical methods for monitoring aromatic contaminants in water, soil, sediment, and air samples.
Acenaphthene supports chromatographic calibration procedures used to separate and quantify polycyclic aromatic hydrocarbon mixtures.
Acenaphthene provides a defined retention profile for gas chromatography and liquid chromatography under properly selected conditions.
Acenaphthene functions as an analytical standard in mass-spectrometric and spectroscopic investigations of aromatic hydrocarbons.
Acenaphthene facilitates compound identification by supplying characteristic molecular, fragmentation, and absorption data.
Acenaphthene enables laboratories to evaluate extraction and sample-preparation methods for hydrophobic organic contaminants.
Acenaphthene provides a representative low-molecular-weight polycyclic aromatic compound for recovery and detection studies.
Acenaphthene contributes to environmental-fate studies examining volatilization, sorption, biodegradation, and photochemical transformation.
Acenaphthene allows researchers to investigate how fused aromatic hydrocarbons behave in different environmental compartments.
Acenaphthene supports toxicological and ecotoxicological research conducted to characterize the behavior of polycyclic aromatic hydrocarbons.
Acenaphthene provides a standardized test substance for controlled laboratory studies when appropriate safety and regulatory procedures are followed.
Acenaphthene serves as a model compound in oxidation research involving polycyclic and fused-ring aromatic hydrocarbons.
Acenaphthene enables researchers to study the formation of ketones, quinones, carboxylic derivatives, and other oxidation products.
Acenaphthene facilitates investigations of electrophilic aromatic substitution because the fused-ring system contains several chemically accessible positions.
Acenaphthene allows comparative studies of nitration, sulfonation, bromination, chlorination, and related reactions.
Acenaphthene supports hydrogenation and dehydrogenation research involving the relationship between acenaphthene and acenaphthylene structures.
Acenaphthene provides a useful molecular platform for studying catalyst selectivity and reaction conditions in fused-ring hydrocarbon conversion.
Acenaphthene contributes to thermal-analysis studies focused on melting, crystallization, vaporization, and phase-transition behavior.
Acenaphthene enables researchers to evaluate the physical behavior of a relatively low-melting polycyclic aromatic solid.
Acenaphthene offers a reference material for investigating crystal structure, molecular packing, and intermolecular interactions.
Acenaphthene supports studies connecting molecular geometry with melting behavior, density, and solid-state organization.
Acenaphthene finds application in photochemical and spectroscopic research involving fused aromatic hydrocarbons.
Acenaphthene provides a suitable structure for examining ultraviolet absorption, fluorescence behavior, and light-induced transformation.
Acenaphthene supports the preparation of carbon-rich precursors for research into advanced carbonaceous materials.
Acenaphthene contributes a compact aromatic structure that can undergo controlled thermal conversion under specialized experimental conditions.
Acenaphthene enables the synthesis of substituted acenaphthenes designed for materials-science and molecular-electronics investigations.
Acenaphthene allows electronic properties to be adjusted through controlled introduction of electron-donating or electron-withdrawing groups.
Acenaphthene functions as a chemical intermediate in custom organic synthesis requiring a stable hydrocarbon scaffold with defined reactivity.
Acenaphthene helps manufacturers obtain higher-value aromatic compounds through carefully selected multistage processing routes.
DESCRIPTION
Acenaphthene is a polycyclic aromatic hydrocarbon generally encountered as white, colorless, or pale-yellow crystals, flakes, or crystalline powder.
Acenaphthene may gradually develop a darker appearance when impurities are present or when Acenaphthene is exposed to unsuitable processing and storage conditions.
Structurally, Acenaphthene consists of a naphthalene ring system in which the peri positions are connected by a saturated two-carbon bridge.
Acenaphthene therefore contains two fused benzene-related rings together with a five-membered ring formed by the ethylene bridge.
Chemically, Acenaphthene has the molecular formula C12H10 and a molecular weight of approximately 154.21 g/mol.
Acenaphthene differs from acenaphthylene because Acenaphthene contains a saturated carbon–carbon bridge rather than a double bond in the five-membered ring.
Because of its compact fused-ring framework, Acenaphthene exhibits the hydrophobic behavior typical of polycyclic aromatic hydrocarbons.
Acenaphthene also provides a stable aromatic nucleus that can undergo controlled substitution and oxidation during industrial synthesis.
Acenaphthene occurs naturally as a component of coal tar and can be recovered from high-boiling aromatic fractions generated during coal processing.
Acenaphthene is commonly separated from related hydrocarbons through fractional distillation, cooling, crystallization, and purification procedures.
During commercial production, Acenaphthene-containing fractions may be refined to remove naphthalene, fluorene, acenaphthylene, and other neighboring aromatic components.
Acenaphthene purity and appearance depend on the efficiency of fractionation, crystallization, washing, and final finishing operations.
Acenaphthene functions mainly as an intermediate rather than as a finished formulation ingredient.
Acenaphthene becomes more valuable after oxidation, nitration, halogenation, sulfonation, or other reactions introduce functional groups for downstream processing.
Oxidation converts Acenaphthene into acenaphthenequinone, one of the most important derivatives obtained from Acenaphthene.
Acenaphthenequinone provides two adjacent carbonyl groups that support condensation, ligand formation, dye synthesis, and specialty-material development.
Acenaphthene can also undergo dehydrogenation to form acenaphthylene under suitable catalytic or thermal conditions.
Acenaphthene may be regenerated from acenaphthylene through controlled hydrogenation of the carbon–carbon double bond.
Owing to its nonpolar aromatic structure, Acenaphthene is practically insoluble in water.
Acenaphthene nevertheless dissolves more readily in aromatic hydrocarbons, ethers, chlorinated solvents, and various other suitable organic media.
The solubility of Acenaphthene increases with temperature in many organic solvents, supporting recrystallization and purification processes.
Acenaphthene solvent compatibility must still be evaluated for each application because concentration, temperature, purity, and solvent composition influence performance.
Acenaphthene melts at approximately 93–96 °C, although the measured value can vary slightly with purity and analytical method.
Acenaphthene has a normal boiling point of approximately 279 °C, reflecting the relatively low molecular weight of the fused-ring structure.
When heated above its melting range, Acenaphthene forms a combustible liquid that requires controlled processing and suitable ventilation.
Acenaphthene can release flammable vapors at elevated temperatures and should therefore be kept away from sparks, flames, and other ignition sources.
Under recommended conditions, Acenaphthene remains stable in tightly closed containers stored in a cool, dry, and well-ventilated location.
Acenaphthene should be protected from strong oxidizing agents, excessive heat, and conditions that encourage vapor or dust accumulation.
Another important feature of Acenaphthene is the relative rigidity of the fused aromatic framework.
Acenaphthene combines this structural rigidity with sufficient chemical reactivity to support numerous downstream transformations.
During industrial handling, Acenaphthene may generate dust when supplied as crystals, flakes, or powder.
Acenaphthene should therefore be transferred with equipment and procedures that minimize airborne particles and unnecessary workplace contamination.
Compared with simpler aromatic hydrocarbons, Acenaphthene offers additional synthetic possibilities through the bridged five-membered ring.
Acenaphthene consequently provides a useful balance of aromatic stability, oxidation reactivity, and functionalization potential.
As a result, Acenaphthene remains an important intermediate for dyes, pigments, resins, agrochemical precursors, analytical standards, and specialty organic compounds.
Acenaphthene also continues to support research in environmental analysis, catalysis, spectroscopy, materials science, and polycyclic aromatic chemistry.
PROPERTIES
Appearance: White to pale-yellow crystalline solid
Odor: Characteristic aromatic odor
Molecular Formula: C12H10
Molecular Weight: 154.21 g/mol
Melting Point: Approximately 93–96 °C
Boiling Point: Approximately 279 °C
Solubility in Water: Practically insoluble
Solubility in Organic Solvents: Soluble in various aromatic and nonpolar organic solvents
Physical Form: Crystals, flakes, or crystalline powder
Stability: Stable under normal recommended storage conditions
FIRST AID
Inhalation: Move the exposed person to fresh air and keep the person comfortable for breathing. Obtain medical attention if coughing, dizziness, breathing difficulty, or other symptoms persist.
Skin Contact: Remove contaminated clothing and wash the affected area thoroughly with soap and water. Seek medical advice if irritation develops or continues.
Eye Contact: Rinse cautiously with clean water for several minutes. Remove contact lenses when present and easy to do, then continue rinsing. Obtain medical attention if discomfort or irritation persists.
Ingestion: Rinse the mouth with water. Do not induce vomiting unless directed by qualified medical personnel. Obtain medical advice if a significant quantity has been swallowed or symptoms develop.
Note to Physicians: Provide symptomatic and supportive treatment according to the exposed person’s condition and the available safety information for the supplied grade.
HANDLING AND STORAGE
Handling: Avoid breathing Acenaphthene dust or heated vapors. Prevent contact with the skin, eyes, and clothing, and keep Acenaphthene away from ignition sources.
Ventilation: Provide adequate general ventilation and use local exhaust ventilation where Acenaphthene dust, fumes, or vapors may be generated.
Storage: Store Acenaphthene in a tightly closed container in a cool, dry, and well-ventilated area away from strong oxidizing agents, heat, sparks, and open flames.
Spill and Leak Procedures: Eliminate ignition sources, avoid dispersing Acenaphthene dust, and collect spilled material with suitable non-sparking equipment for recovery or disposal.
Handling Precautions: Use suitable personal protective equipment, wash thoroughly after handling Acenaphthene, and keep containers closed when not in use.
