ANTHRAQUINONE

Anthraquinone is a conjugated aromatic quinone compound containing a rigid three-ring molecular framework.
Anthraquinone serves as an important intermediate in the manufacture of dyes, pigments, pulp-processing chemicals, peroxide-production intermediates, and specialty organic derivatives.
Anthraquinone is generally supplied as a yellow to pale-yellow crystalline powder with very low water solubility and high thermal stability.

CAS Number: 84-65-1
EC Number: 201-549-0
Molecular Formula: C14H8O2
Molecular Weight: 208.21 g/mol

SYNONYMS

9,10-Anthraquinone, Anthracene-9,10-dione, 9,10-Anthracenedione, Anthracene-9,10-quinone, 9,10-Anthracenequinone, Anthra-9,10-quinone, 9,10-Dioxoanthracene, Anthracene-9,10-diketone, 9,10-Anthracenediketone, 9,10-Dihydro-9,10-dioxoanthracene, 9,10-Dihydroanthracene-9,10-dione, Anthracene, 9,10-dihydro-9,10-dioxo-, Anthradione, Anthracenedione, Anthracenequinone, Anthraquinon, Anthrachinone, Anthrachinon, 9,10-Anthrachinon, Antrachinon, Antrachinon-9,10, Antraquinone, Antraquinona, Antrakinon, Antrachinone, Antrakinona, Anthraquinonum, Anthraquinone AQ, AQ, 9,10-AQ, Anthraquinone 84-65-1, 9,10-Anthraquinone 84-65-1, Anthracene-9,10-dione 84-65-1, 9,10-Anthracenedione 84-65-1, Anthraquinone C14H8O2, Hoelite, Morkit, Corbit, NSC 7957, NSC-7957, NSC7957, Caswell No. 052A, EINECS 201-549-0, EC 201-549-0, EC Number 201-549-0, CAS 84-65-1, CAS-84-65-1, CAS Number 84-65-1, PubChem CID 6780, CID 6780, MFCD00001188, CHEBI 40448, CHEBI:40448, ChEBI 40448, UNII-030MS0JBDO, 030MS0JBDO, DTXSID3020095, DTXCID9095, HSDB 2074, CCRIS 649, EPA Pesticide Chemical Code 122701, RZVHIXYEVGDQDX-UHFFFAOYSA-N, InChIKey RZVHIXYEVGDQDX-UHFFFAOYSA-N

APPLICATIONS

Anthraquinone serves as a fundamental intermediate in the manufacture of anthraquinone dyes for textile, plastics, coating, ink, and specialty-colorant applications.
Anthraquinone provides a stable conjugated framework that can be modified to produce red, orange, violet, blue, green, brown, and related color ranges.

Anthraquinone functions as a starting material for vat dyes requiring strong coloration and reversible reduction–oxidation behavior.
Anthraquinone supports the preparation of dye structures capable of producing durable shades on cotton and other cellulosic fibers.

Anthraquinone contributes to disperse-dye manufacture by providing a rigid aromatic nucleus suitable for coloring hydrophobic synthetic materials.
Anthraquinone enables substitution patterns to be adjusted for improved shade, sublimation resistance, molecular size, and polyester affinity.

Anthraquinone facilitates the production of solvent dyes for plastics, waxes, fuels, lubricants, lacquers, coatings, and printing inks.
Anthraquinone allows suitable functional groups to be introduced for improved solubility in nonaqueous media and stronger color development.

Anthraquinone enhances pigment-intermediate synthesis through reactions that form highly conjugated and structurally durable colorant molecules.
Anthraquinone supports pigment systems requiring resistance to heat, light, chemicals, migration, and demanding processing conditions.

Anthraquinone finds application in the preparation of acid-dye intermediates following sulfonation and further functionalization.
Anthraquinone provides a versatile platform for introducing water-solubilizing groups and textile-affinity functions into selected dye molecules.

Anthraquinone promotes reactive-dye intermediate synthesis by supporting the introduction of amino, hydroxy, sulfonic acid, and reactive substituents.
Anthraquinone helps manufacturers develop colorants that combine vivid shades with controlled bonding or interaction with textile fibers.

Anthraquinone supports the production of mordant dyes containing groups capable of interacting with selected metal ions.
Anthraquinone allows coordinating functionality to be incorporated for controlled shade, fixation, and substrate affinity.

Anthraquinone serves as a precursor for alizarin and related hydroxyanthraquinone compounds used in dye and pigment chemistry.
Anthraquinone facilitates hydroxylation routes that provide intermediates with distinctive shades, acidity, coordination behavior, and chemical reactivity.

Anthraquinone functions as a starting material for quinizarin and other dihydroxyanthraquinone derivatives.
Anthraquinone enables hydroxyl-group positioning to be selected according to the required color and downstream reaction pathway.

Anthraquinone contributes to aminoanthraquinone production through nitration followed by controlled reduction or through suitable substitution reactions.
Anthraquinone supports the manufacture of important intermediates for disperse, solvent, vat, and specialty dyes.

Anthraquinone facilitates the production of halogenated anthraquinone intermediates used in nucleophilic substitution and coupling reactions.
Anthraquinone provides a thermally stable core that tolerates controlled chlorination or bromination before further conversion.

Anthraquinone enables the manufacture of anthraquinone sulfonic acids and their salts for colorant and specialty-chemical synthesis.
Anthraquinone gains improved water compatibility and additional reaction possibilities after sulfonic acid groups are introduced.

Anthraquinone offers a useful starting point for producing alkylated anthraquinone derivatives employed in hydrogen peroxide manufacture.
Anthraquinone provides the quinone framework required for repeated hydrogenation and oxidation cycles in the working solution.

Anthraquinone supports hydrogen peroxide generation through derivatives that alternate between quinone and anthrahydroquinone forms.
Anthraquinone enables oxygen to be converted indirectly into hydrogen peroxide while the working intermediate is regenerated.

Anthraquinone functions as a processing aid in selected alkaline pulp-manufacturing systems.
Anthraquinone participates in reversible redox reactions that can accelerate delignification under appropriately controlled cooking conditions.

Anthraquinone contributes to improved pulp yield by helping protect carbohydrate fractions from excessive degradation.
Anthraquinone may also support reduced cooking severity, shorter processing time, or improved lignin removal depending on operating conditions.

Anthraquinone facilitates kraft-pulping and soda-pulping research aimed at improving chemical efficiency and fiber preservation.
Anthraquinone allows pulp manufacturers to evaluate the balance between delignification rate, alkali demand, pulp yield, and final fiber quality.

Anthraquinone serves as a redox-active compound in electrochemical and energy-storage research.
Anthraquinone provides two conjugated carbonyl groups capable of participating in reversible electron-transfer reactions.

Anthraquinone supports the development of organic electrode materials for rechargeable battery systems.
Anthraquinone enables researchers to investigate charge-storage capacity, reduction potential, cycling stability, and electrode compatibility.

Anthraquinone contributes to the preparation of redox-active polymers containing pendant or backbone-integrated quinone structures.
Anthraquinone allows polymer properties to be adjusted through changes in substitution, linkage type, molecular mobility, and electrolyte compatibility.

Anthraquinone finds application in aqueous and nonaqueous redox-flow battery research through suitably soluble derivatives.
Anthraquinone provides a modifiable molecular platform for controlling redox potential, solubility, stability, and membrane crossover.

Anthraquinone promotes the development of electrochemical sensors because the quinone structure responds to changes in electron and proton availability.
Anthraquinone enables functional electrodes to be designed for analytical, biological, and environmental detection research.

Anthraquinone supports molecular-electronics studies involving redox switching and charge transport.
Anthraquinone allows electrical conductance to be influenced through reversible conversion between quinone and reduced forms.

Anthraquinone facilitates optoelectronic research through derivatives with tunable absorption, emission, and electron-accepting characteristics.
Anthraquinone provides a conjugated aromatic system that can be modified with electron-donating or electron-withdrawing substituents.

Anthraquinone contributes to the synthesis of fluorescent probes and chromophores used in chemical and materials research.
Anthraquinone enables optical behavior to be adjusted through changes in substitution pattern, conjugation, polarity, and molecular environment.

Anthraquinone offers a platform for preparing photoactive molecules capable of participating in light-induced electron-transfer processes.
Anthraquinone supports photochemical studies involving excited states, energy transfer, reduction, oxidation, and radical formation.

Anthraquinone functions as a scaffold in medicinal-chemistry and pharmaceutical-intermediate research.
Anthraquinone allows hydroxy, amino, alkyl, halogen, glycoside, and heterocyclic groups to be introduced for structure–activity investigations.

Anthraquinone supports the preparation of specialty organic compounds evaluated in biochemical and molecular-recognition studies.
Anthraquinone provides a rigid planar structure capable of interacting with different molecular environments after appropriate functionalization.

Anthraquinone enables the development of fine-chemical intermediates through nitration, sulfonation, halogenation, amination, and hydroxylation.
Anthraquinone helps manufacturers create higher-value compounds from a stable and chemically versatile aromatic core.

Anthraquinone contributes to agrochemical-intermediate research where substituted aromatic quinones are required in multistep synthesis.
Anthraquinone permits functional groups to be introduced at several aromatic positions according to the targeted downstream structure.

Anthraquinone supports the manufacture of specialty polymer intermediates containing rigid aromatic and carbonyl functionality.
Anthraquinone may contribute to thermal resistance, structural rigidity, or redox behavior after suitable derivatives are incorporated into polymer systems.

Anthraquinone facilitates the development of polymeric colorants designed to reduce migration or improve compatibility with selected matrices.
Anthraquinone enables color-forming groups to be chemically connected to larger molecular or polymeric structures.

Anthraquinone finds application in coating research involving redox-active, light-absorbing, or color-producing functional materials.
Anthraquinone provides a durable aromatic structure that can be attached to binders, particles, surfaces, or functional additives.

Anthraquinone promotes the preparation of organic semiconductor materials through derivatives with controlled molecular packing and electron affinity.
Anthraquinone enables electronic properties to be adjusted by modifying the aromatic rings or extending conjugation.

Anthraquinone supports catalyst and photocatalyst research when anthraquinone derivatives are immobilized on polymers, particles, or porous supports.
Anthraquinone provides redox and light-absorption functions that can assist specialized electron-transfer processes.

Anthraquinone contributes to ligand and coordination-chemistry research through derivatives containing suitable donor groups.
Anthraquinone allows metal-binding behavior to be combined with the optical and electrochemical properties of the quinone framework.

Anthraquinone serves as a model compound in studies of quinone reduction, oxidation, substitution, and carbonyl reactivity.
Anthraquinone enables researchers to examine reaction mechanisms within a stable and well-defined conjugated system.

Anthraquinone facilitates investigations of proton-coupled electron transfer involving aromatic quinones.
Anthraquinone provides a useful reference structure for comparing solvent, pH, substituent, and electrode effects.

Anthraquinone supports crystallographic and solid-state studies involving planar aromatic molecules.
Anthraquinone allows researchers to examine molecular packing, intermolecular interactions, crystal morphology, and thermal transitions.

Anthraquinone contributes to spectroscopy research using ultraviolet-visible, infrared, Raman, nuclear magnetic resonance, and mass-spectrometric techniques.
Anthraquinone provides characteristic signals associated with the aromatic framework and conjugated carbonyl groups.

Anthraquinone enables chromatographic method development for detecting and quantifying aromatic quinone compounds.
Anthraquinone serves as a defined analytical reference in gas, liquid, and thin-layer chromatographic procedures.

Anthraquinone finds application in environmental analysis as a reference compound for monitoring industrial and combustion-related aromatic substances.
Anthraquinone allows laboratories to assess extraction, recovery, separation, identification, and quantification procedures.

Anthraquinone supports environmental-fate research involving sorption, degradation, photolysis, transport, and persistence.
Anthraquinone provides a representative aromatic quinone for comparing behavior in water, soil, sediment, and atmospheric particles.

Anthraquinone functions as a starting material for custom synthesis projects requiring a rigid quinone-based molecular scaffold.
Anthraquinone helps synthetic chemists introduce multiple functional groups while retaining the central anthraquinone framework.

Anthraquinone enables the preparation of porous organic materials and functional networks containing redox-active carbonyl groups.
Anthraquinone contributes to research involving gas interaction, charge storage, molecular adsorption, and catalytic support materials.

Anthraquinone offers potential utility in carbon dioxide capture and conversion research through suitably functionalized derivatives.
Anthraquinone allows quinone redox behavior to be combined with chemical groups capable of interacting with carbon dioxide.

Anthraquinone supports surface-modification studies in which redox-active aromatic units are attached to electrodes or solid supports.
Anthraquinone provides an electrochemically responsive layer that can be investigated for sensing, catalysis, and charge-transfer applications.

Anthraquinone facilitates the preparation of analytical reagents and indicators based on substituted hydroxyanthraquinone structures.
Anthraquinone enables acidity, metal coordination, water compatibility, and visible response to be controlled through substitution.

Anthraquinone contributes to research into reversible color changes associated with reduction, oxidation, protonation, or metal binding.
Anthraquinone provides a chromophoric system whose optical behavior responds to changes in molecular structure and electronic state.

Anthraquinone serves as a versatile intermediate for producing specialty compounds with tailored solubility, polarity, shade, and reactivity.
Anthraquinone allows manufacturers and researchers to select different substitution pathways according to the intended product performance.

DESCRIPTION

Anthraquinone is an aromatic quinone generally encountered as a yellow, pale-yellow, greenish-yellow, or yellowish crystalline solid.
Anthraquinone may be supplied as crystals, flakes, granules, or finely divided powder depending on purification, crystallization, milling, and finishing conditions.

Structurally, Anthraquinone contains three fused six-membered rings derived from the anthracene framework.
Anthraquinone carries two opposing carbonyl groups at the 9- and 10-positions of the central ring.

Chemically, Anthraquinone has the molecular formula C14H8O2 and a molecular weight of approximately 208.21 g/mol.
Anthraquinone combines an extended aromatic system with two conjugated ketone groups that strongly influence electronic behavior and chemical reactivity.

Because of its fused and conjugated molecular structure, Anthraquinone forms the parent framework of a large family of industrial colorants.
Anthraquinone itself is normally pale yellow, while suitably substituted derivatives can produce much stronger and more varied shades.

The two carbonyl groups of Anthraquinone withdraw electron density from the surrounding aromatic system.
Anthraquinone consequently displays electron-accepting and reversible redox characteristics that support several industrial and research applications.

Anthraquinone possesses a relatively planar and rigid molecular geometry.
Anthraquinone planarity contributes to strong intermolecular interactions, efficient crystal packing, and a high melting range.

Anthraquinone can be manufactured by oxidation of anthracene using air, nitric acid, chromic acid, or suitable catalytic oxidation systems.
Anthraquinone production by anthracene oxidation converts the central aromatic ring into a conjugated diketone structure.

Anthraquinone may also be produced through a route involving phthalic anhydride and benzene followed by cyclization.
Anthraquinone manufacturing processes can additionally use naphthoquinone, butadiene, or other aromatic intermediates in suitable multistage routes.

During industrial production, Anthraquinone is separated from unreacted raw materials, oxidation by-products, and related aromatic compounds.
Anthraquinone purification may involve crystallization, washing, filtration, sublimation, solvent treatment, or combinations of these operations.

Anthraquinone purity depends on the quality of the starting material, oxidation selectivity, reaction temperature, catalyst performance, and purification efficiency.
Anthraquinone intended for sensitive dye or fine-chemical synthesis generally requires tighter control of anthracene and other aromatic impurities.

In its commercial form, Anthraquinone is primarily supplied as an industrial intermediate rather than as a finished formulation ingredient.
Anthraquinone grades may differ in purity, particle size, color, moisture content, ash content, and trace-impurity profile.

Anthraquinone functions as a versatile reaction platform because several positions on the fused aromatic rings can be chemically modified.
Anthraquinone undergoes nitration, sulfonation, halogenation, hydroxylation, amination, alkylation, condensation, reduction, and oxidation under suitable conditions.

Nitration allows Anthraquinone to form nitroanthraquinone intermediates at selected ring positions.
Anthraquinone nitro derivatives can subsequently be reduced to aminoanthraquinones used extensively in colorant synthesis.

Sulfonation introduces one or more sulfonic acid groups into the Anthraquinone structure.
Anthraquinone sulfonic acid derivatives display improved water compatibility and provide useful reaction sites for further transformation.

Halogenation converts Anthraquinone into chloroanthraquinone, bromoanthraquinone, or related intermediates.
Anthraquinone halogen derivatives can undergo displacement reactions with amino, hydroxy, alkoxy, or other nucleophilic groups.

Hydroxylation produces hydroxyanthraquinones such as alizarin, quinizarin, and structurally related compounds.
Anthraquinone hydroxy derivatives exhibit altered acidity, color, metal-binding behavior, solubility, and substrate interaction.

Amination produces aminoanthraquinones with strong chromophoric behavior and extensive use in dye chemistry.
Anthraquinone amino derivatives can be further alkylated, acylated, sulfonated, halogenated, or condensed to adjust performance.

Reduction converts Anthraquinone into anthrahydroquinone or partially hydrogenated forms depending on the reaction conditions.
Anthraquinone can return to the quinone state after oxidation, allowing reversible redox cycles to occur.

This reversible behavior allows Anthraquinone derivatives to function in hydrogen peroxide manufacturing processes.
Anthraquinone-based working compounds alternate between hydrogenated and oxidized forms while assisting peroxide generation.

Anthraquinone redox behavior also supports its application in alkaline pulping.
Anthraquinone can participate in electron-transfer reactions that promote lignin removal and help preserve carbohydrate fractions.

Owing to its nonpolar aromatic framework, Anthraquinone is practically insoluble or only very slightly soluble in water.
Anthraquinone therefore remains predominantly as a solid or dispersed phase in many aqueous processing systems.

Anthraquinone dissolves to varying degrees in selected aromatic, chlorinated, polar aprotic, and high-boiling organic solvents.
Anthraquinone solubility depends on solvent identity, temperature, concentration, purity, crystal form, and particle size.

Elevated temperature generally increases the dissolution rate and solubility of Anthraquinone in suitable organic media.
Anthraquinone may consequently be purified or processed through hot-solvent dissolution followed by controlled crystallization.

Anthraquinone has a high melting range, commonly reported at approximately 284–286 °C.
Anthraquinone may sublime under sufficiently high temperature or reduced-pressure conditions because of its stable aromatic structure.

The high melting behavior of Anthraquinone reflects the rigidity and strong intermolecular attraction of the planar molecules.
Anthraquinone remains solid under processing conditions that would melt many lower-molecular-weight aromatic intermediates.

Anthraquinone displays low volatility at ordinary temperatures.
Anthraquinone dust may nevertheless become airborne during grinding, conveying, charging, packaging, or other powder-handling operations.

Under normal recommended storage conditions, Anthraquinone demonstrates good chemical and thermal stability.
Anthraquinone should be protected from excessive heat, strong reducing agents, powerful oxidizing agents, flames, and incompatible reactive materials.

Exposure to intense heat may cause Anthraquinone to sublime, decompose, or release irritating combustion products.
Anthraquinone processing equipment should therefore provide suitable temperature control and ventilation.

When incorporated into colorant synthesis, Anthraquinone supplies a durable aromatic skeleton that tolerates extensive chemical modification.
Anthraquinone allows shade, solubility, polarity, fiber affinity, migration behavior, and fastness to be adjusted through substitution.

The conjugated structure of Anthraquinone supports absorption of ultraviolet and visible radiation.
Anthraquinone derivatives display altered absorption characteristics when electron-donating or electron-withdrawing groups are attached.

Amino groups generally increase electron donation into the Anthraquinone chromophore.
Anthraquinone amino derivatives can consequently produce deeper and more intense colors than unsubstituted Anthraquinone.

Hydroxy groups alter the electronic, acidic, and coordination properties of the Anthraquinone system.
Anthraquinone hydroxy derivatives may interact with metal ions and treated substrates through suitably positioned oxygen atoms.

Sulfonic acid groups increase the hydrophilic character of Anthraquinone derivatives.
Anthraquinone sulfonates are therefore more compatible with water-based synthesis and application systems than unsubstituted Anthraquinone.

Alkyl and aryl substitution can alter the solubility and organic-medium compatibility of Anthraquinone derivatives.
Anthraquinone substituent selection also affects crystallinity, melting behavior, migration resistance, and intermolecular association.

The carbonyl groups of Anthraquinone can accept electrons during electrochemical reduction.
Anthraquinone subsequently releases electrons during oxidation, supporting reversible charge-storage and switching behavior.

Anthraquinone derivatives may be attached to polymer chains, porous frameworks, electrode surfaces, or solid particles.
Anthraquinone immobilization can reduce molecular loss while preserving useful redox or optical characteristics.

Another important feature of Anthraquinone is the ability to support proton-coupled electron-transfer reactions.
Anthraquinone reduction behavior can therefore vary with solvent polarity, proton availability, pH, electrolyte, and substitution pattern.

During industrial processing, Anthraquinone particle size influences charging, dispersion, dissolution, filtration, and reaction consistency.
Anthraquinone supplied as a fine powder generally requires stronger dust-control measures than coarse crystals or granules.

Anthraquinone color and appearance can be affected by trace anthracene, oxidation by-products, inorganic residues, or other aromatic impurities.
Anthraquinone specifications should consequently be matched to the sensitivity and color requirements of the downstream process.

Anthraquinone compatibility with polymers, resins, coatings, and organic media depends strongly on the selected grade and chemical form.
Anthraquinone derivatives are often preferred when unsubstituted Anthraquinone lacks sufficient solubility or matrix interaction.

Compared with simpler quinones, Anthraquinone offers a larger, more rigid, and more extensively conjugated molecular system.
Anthraquinone consequently provides greater structural versatility for developing dyes, pigments, redox materials, sensors, and functional intermediates.

Compared with anthracene, Anthraquinone contains two carbonyl groups that increase polarity and redox reactivity.
Anthraquinone nevertheless retains the rigid fused-ring character and thermal stability associated with the anthracene skeleton.

Under analytical conditions, Anthraquinone can be identified by chromatographic, spectroscopic, and thermal-analysis techniques.
Anthraquinone produces characteristic responses associated with its aromatic rings, conjugated carbonyl groups, molecular mass, and crystal structure.

As a result, Anthraquinone combines aromatic stability, carbonyl reactivity, derivatization potential, and useful redox behavior.
Anthraquinone remains an important raw material for colorants, pulp processing, peroxide technology, fine chemicals, analytical standards, and advanced materials.

PROPERTIES

Appearance: Yellow to pale-yellow crystalline powder
Odor: Slight or nearly odorless
Molecular Formula: C14H8O2
Molecular Weight: 208.21 g/mol
Melting Point: Approximately 284–286 °C
Solubility in Water: Practically insoluble
Solubility in Organic Solvents: Soluble to varying degrees in selected organic solvents
Physical Form: Crystals, flakes, granules, or 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, breathing difficulty, dizziness, or other symptoms persist.

Skin Contact: Remove contaminated clothing and wash the affected skin 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 Anthraquinone dust and prevent contact with the skin, eyes, and clothing. Use suitable personal protective equipment during transfer and processing.

Ventilation: Provide adequate general ventilation and use local exhaust ventilation where Anthraquinone dust may be generated.

Storage: Store Anthraquinone in a tightly closed container in a cool, dry, and well-ventilated area away from heat and incompatible materials.

Spill and Leak Procedures: Avoid dispersing Anthraquinone dust and collect spilled material carefully using suitable equipment. Transfer Anthraquinone into a properly labeled container for recovery or disposal.

Handling Precautions: Wash thoroughly after handling Anthraquinone and keep containers closed when not in use. Follow the applicable safety data sheet and workplace procedures for the supplied grade.