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1-Nitronaphthalene is a nitroaromatic compound consisting of a naphthalene ring system substituted with a nitro group at the 1-position.
1-Nitronaphthalene is principally used as a chemical intermediate in aromatic synthesis, particularly in routes leading to 1-naphthylamine, naphthalene sulfonic acid derivatives, dinitronaphthalenes, dyes, and related specialty chemicals.
Its defined nitroaromatic structure also makes 1-Nitronaphthalene important in analytical chemistry, combustion-emission studies, environmental monitoring, and research involving nitro-polycyclic aromatic compounds.
CHEMICAL IDENTITY AND COMMON NAMES
1-Nitronaphthalene is the alpha isomer of mononitronaphthalene and contains its nitro group at the 1-position of the naphthalene nucleus.
The alternative positional isomer 2-nitronaphthalene contains the nitro group at the 2-position and possesses a separate chemical identity, CAS number, physical-property profile, and reaction behaviour.
The traditional name alpha-nitronaphthalene reflects substitution at an alpha position of the naphthalene ring.
Historical chemical literature may therefore use 1-Nitronaphthalene and alpha-nitronaphthalene interchangeably.
Nitrol is another historical name associated with 1-Nitronaphthalene.
The registry name naphthalene, 1-nitro- describes the same molecular structure directly.
Synonyms and Common Names: α-Nitronaphthalene, alpha-Nitronaphthalene, Naphthalene, 1-nitro-, Naphthalene, alpha-nitro-, 1-Nitro-naphthalene, 1-Nitronaphthaline, 1-Nitronaphthalin, 1-Nitronaftalen, Nitrol, Alpha-nitro-naphthalene, α-Nitro-naphthalene
TECHNICAL IDENTIFICATION
CAS Number: 86-57-7
EC / EINECS Number: 201-684-5
Molecular Formula: C10H7NO2
Molar Mass: 173.17 g/mol
Chemical Class: Nitroaromatic compound
Structural Type: Mononitro-substituted naphthalene
IUPAC Name: 1-Nitronaphthalene
UN Number: 2538
PHYSICAL AND CHEMICAL PROPERTIES
Appearance: Pale yellow to yellow crystalline solid
Crystal Form: Commonly described as pale yellow needles
Odour: Essentially odourless
Physical State: Solid at ordinary ambient temperature
Molecular Formula: C10H7NO2
Molar Mass: 173.17 g/mol
Melting Point: Approximately 54–57 °C
Boiling Point: Approximately 304 °C
Water Solubility: Low
Relative Water Behaviour: Insoluble to only slightly soluble in water
Organic Solvent Behaviour: Soluble in suitable organic solvents
Vapour Pressure: Low at ambient temperature
Log Kow: Approximately 3.2
Volatility: Low compared with lower-molecular-weight aromatic solvents
Combustibility: Combustible and classified for transport as a flammable solid
Chemical Functionality: Aromatic nitro group
Reduction Behaviour: Reducible to the corresponding naphthylamine
Electrophilic Substitution Behaviour: Further aromatic substitution can provide sulfonated or nitrated derivatives
Thermal Behaviour: Combustion and strong heating can generate nitrogen oxides and carbon oxides
The melting behaviour of 1-Nitronaphthalene makes physical form particularly sensitive to process temperature.
Operations conducted near its melting range can transition the material from a crystalline solid to a liquid phase, which affects pumping, mixing, crystallization, filtration, and packaging.
The fused naphthalene nucleus provides a hydrophobic aromatic framework.
The nitro group adds strong electron-withdrawing character and substantially changes the electronic properties of the ring relative to unsubstituted naphthalene.
The low water affinity of 1-Nitronaphthalene favours organic-phase processing in many synthesis applications.
Solvent selection therefore becomes an important consideration in reduction, substitution, purification, crystallization, and analytical preparation.
FUNCTIONAL CHARACTERISTICS
The nitro group is the principal reactive functionality of 1-Nitronaphthalene.
Reduction converts the nitro group through intermediate oxidation states to the corresponding aromatic amino group, providing a direct route to 1-naphthylamine chemistry.
This transformation is one of the most important reasons for the historical industrial significance of 1-Nitronaphthalene.
Aromatic amines derived from the naphthalene framework have served as intermediates for numerous dyes and specialty organic compounds.
The naphthalene nucleus also remains available for further electrophilic substitution.
Controlled sulfonation can introduce sulfonic acid functionality, while additional nitration can produce dinitronaphthalene isomers.
These reactions make 1-Nitronaphthalene useful as an intermediate rather than simply as an isolated end product.
Its value lies in providing a defined 1-substituted naphthalene framework that can be transformed into amino, sulfonic acid, and additional nitro derivatives.
The aromatic structure also provides strong ultraviolet absorption and characteristic chromatographic and mass-spectrometric behaviour.
These properties support its use as an analytical target in studies of combustion emissions and nitroaromatic environmental contaminants.
PRODUCTION AND COMMERCIAL FORM
1-Nitronaphthalene is produced through controlled nitration of naphthalene.
Industrial nitration generates predominantly the alpha-substituted 1-Nitronaphthalene together with a smaller amount of the 2-nitro positional isomer and other process-related components.
The crude nitration mixture can be separated from the acid phase and subsequently purified.
Distillation, crystallization, washing, or combinations of separation methods can be used according to the required purity and process configuration.
Control of isomer composition is important because 1-Nitronaphthalene and 2-nitronaphthalene are chemically distinct materials.
Higher-purity synthesis grades therefore benefit from analytical control of the positional-isomer profile.
Commercial 1-Nitronaphthalene is generally supplied as a crystalline solid or powder.
Laboratory and analytical applications may use higher-purity material or prepared reference solutions.
The product can also be handled in molten form within appropriately designed industrial equipment when processing temperature is maintained above its melting range.
Molten handling requires effective temperature control and prevention of unnecessary overheating.
APPLICATIONS AND INDUSTRIES
1-NAPHTHYLAMINE INTERMEDIATE
One of the principal established chemical transformations of 1-Nitronaphthalene is reduction to 1-naphthylamine.
Conversion of the nitro group into an amino group produces an important aromatic amine intermediate while retaining the 1-substituted naphthalene skeleton.
Reduction can be performed through appropriately designed catalytic or chemical reduction technology.
The downstream 1-naphthylamine can subsequently participate in diazotization, coupling, substitution, and other aromatic reactions.
1-Nitronaphthalene therefore historically served as an upstream intermediate for chemical value chains requiring 1-naphthylamine.
Purity and positional-isomer control can be important because nitronaphthalene isomers generate corresponding amine isomers during reduction.
DYE INTERMEDIATE CHEMISTRY
1-Nitronaphthalene has an established history as an intermediate in the manufacture of dyes and dye intermediates.
Its importance is closely connected with conversion to amino and sulfonated naphthalene derivatives.
Reduction to 1-naphthylamine introduces the amino functionality required for diazotization and azo-coupling chemistry.
Further substitution can create more highly functionalized intermediates with different aqueous behaviour, coupling characteristics, and chromophoric properties.
Naphthalene-based aromatic intermediates have been important building blocks in classical synthetic dye chemistry because the fused-ring structure extends conjugation and provides several positions for controlled functionalization.
1-Nitronaphthalene provides one route into this family of materials.
SULFONATED DYE INTERMEDIATES
1-Nitronaphthalene can undergo sulfonation to form nitronaphthalene sulfonic acid derivatives.
1-Nitronaphthalene-5-sulfonic acid is an established example associated with dye-intermediate chemistry.
Introduction of a sulfonic acid group changes the aqueous and ionic behaviour of the aromatic molecule.
The sulfonated intermediate can subsequently undergo reduction or other transformations to produce functional naphthalene intermediates used in colorant synthesis.
The sequence of nitration, sulfonation, reduction, and further substitution allows manufacturers to control the final substitution pattern on the naphthalene ring.
This positional control is critical because different naphthalene isomers can generate substantially different dyes.
DINITRONAPHTHALENE PRODUCTION
Further nitration of 1-Nitronaphthalene can generate dinitronaphthalene derivatives.
1,5-Dinitronaphthalene and 1,8-dinitronaphthalene are important structural products associated with this chemistry.
Reduction of dinitro compounds provides corresponding naphthalenediamines.
These diamines can serve as intermediates for dyes, polymers, specialty aromatic compounds, and other chemical transformations where two amino groups are required on a rigid fused-ring structure.
The substitution pattern obtained during additional nitration therefore determines the structure and usefulness of the resulting downstream diamine.
Process selectivity and isomer separation can consequently become important manufacturing considerations.
AROMATIC AMINE CHEMISTRY
1-Nitronaphthalene serves as a convenient precursor when a chemical process requires conversion from a nitroaromatic compound to a 1-amino-substituted naphthalene.
The nitro-to-amine transformation is a fundamental route in aromatic intermediate manufacture.
The resulting amino functionality can participate in diazotization, acylation, alkylation, condensation, and other reactions.
This chemistry provides access to a much broader family of compounds than could be prepared efficiently from 1-Nitronaphthalene without reduction.
SPECIALTY ORGANIC SYNTHESIS
1-Nitronaphthalene is used as a defined building block in specialty organic synthesis.
Its combination of a fused aromatic nucleus and strongly electron-withdrawing nitro substituent provides a useful platform for studying and controlling aromatic reaction behaviour.
Reduction, further nitration, sulfonation, and other substitution reactions can provide a series of chemically differentiated naphthalene derivatives.
The specific route is selected according to the desired substitution pattern and downstream functionality.
1-Nitronaphthalene is particularly useful where the target compound requires functionalization originating specifically at the 1-position.
The alternative 2-nitro isomer cannot be substituted automatically because it produces a different molecular architecture throughout subsequent synthesis.
PETROLEUM AND MINERAL-OIL DEBLOOMING
1-Nitronaphthalene has historically been used as a deblooming agent for petroleum oils.
In this application, the material suppresses or quenches undesirable fluorescence that can give refined oils a characteristic bloom when viewed under suitable illumination.
The aromatic nitro structure interacts with excited fluorescent species within the oil and can reduce visible fluorescence.
This function historically improved the visual appearance of selected petroleum and mineral-oil products.
This application is now primarily important as part of the established industrial history and fluorescence-quenching behaviour of 1-Nitronaphthalene.
Modern petroleum-processing technologies may use alternative approaches depending on product, jurisdiction, and performance requirements.
FLUORESCENCE QUENCHING
The fluorescence-quenching ability associated with 1-Nitronaphthalene is useful beyond its historical description as a petroleum deblooming agent.
Nitroaromatic compounds can interact efficiently with electronically excited aromatic molecules and reduce fluorescence intensity.
This characteristic makes 1-Nitronaphthalene useful in physical-chemistry and spectroscopy research.
Controlled fluorescence quenching can provide information about molecular interactions, diffusion, solvent effects, and excited-state behaviour.
Analytical and research grades are more appropriate for these applications than technical intermediate grades because unknown fluorescent or quenching impurities can interfere with experimental measurements.
COMBUSTION-EMISSION ANALYSIS
1-Nitronaphthalene is an environmentally relevant nitro-polycyclic aromatic compound associated with combustion emissions.
It has been investigated in diesel exhaust, atmospheric particulate material, and other combustion-derived samples.
Environmental laboratories can therefore use 1-Nitronaphthalene as a target analyte when characterizing nitroaromatic components of air pollution.
Measurement is particularly relevant in studies examining formation and transformation of nitrated polycyclic aromatic hydrocarbons.
1-Nitronaphthalene can be present in both vapour and particulate phases depending on environmental conditions.
Sampling methodology must consequently account for the partitioning behaviour of semivolatile aromatic compounds.
ENVIRONMENTAL MONITORING
1-Nitronaphthalene is used as an analytical reference substance in environmental studies involving air, water, soil, sediment, combustion residues, and contaminated industrial matrices.
Its defined molecular identity supports chromatographic calibration and confirmation.
Gas chromatography combined with mass spectrometry is particularly useful for identification and quantitative measurement.
The characteristic molecular mass and fragmentation pattern allow 1-Nitronaphthalene to be distinguished from many other aromatic compounds.
Environmental analysis must also distinguish 1-Nitronaphthalene from 2-nitronaphthalene.
Chromatographic separation is therefore important when both positional isomers may occur within the same sample.
NITRO-PAH RESEARCH
1-Nitronaphthalene is used in research involving nitrated polycyclic aromatic hydrocarbons.
These studies examine atmospheric chemistry, combustion formation, photochemistry, biological metabolism, environmental transformation, and toxicological behaviour.
The compound provides a relatively simple nitro-PAH structure because it contains one fused bicyclic aromatic system and one nitro group.
This makes it useful for understanding relationships between nitro-group position and chemical or biological behaviour.
Comparative studies with 2-nitronaphthalene and methyl-substituted nitronaphthalenes can help determine how substitution pattern influences reduction, oxidation, mutagenicity, metabolism, and physical properties.
TOXICOLOGICAL AND METABOLISM RESEARCH
1-Nitronaphthalene has been extensively investigated in experimental toxicology as a representative nitroaromatic compound.
Research has examined its metabolism, nitroreduction, oxidation, tissue binding, pulmonary effects, and genotoxic behaviour.
Biological reduction can produce hydroxylamine and amino-related metabolites.
Oxidative metabolism can also generate reactive intermediates associated with tissue effects in experimental systems.
The pulmonary system has received particular attention in mechanistic studies.
1-Nitronaphthalene is therefore useful as a research chemical for investigating relationships between metabolism and target-organ toxicity.
GENOTOXICITY RESEARCH
1-Nitronaphthalene has demonstrated mutagenic activity in bacterial test systems.
This behaviour has contributed to its use in mechanistic research on nitroaromatic mutagenicity.
Nitroreduction can generate reactive intermediates that contribute to interaction with cellular macromolecules.
Comparative testing of 1-Nitronaphthalene and related nitroarenes helps clarify how molecular structure influences biological activation.
Research-grade material with a well-defined impurity profile is particularly important in genotoxicity studies because trace aromatic contaminants can interfere with interpretation.
ANALYTICAL REFERENCE MATERIALS
High-purity 1-Nitronaphthalene is useful as an analytical reference compound.
Applications include calibration, retention-time confirmation, spectral comparison, recovery studies, quantitative method development, and instrument-performance testing.
Gas chromatography is particularly appropriate because the compound possesses sufficient volatility at analytical temperatures while remaining a stable crystalline solid during routine storage.
GC-MS provides additional structural confirmation.
Liquid chromatographic methods can also be used when analytical conditions are designed for nitroaromatic compounds.
UV detection is facilitated by the strong absorption of the aromatic nitro structure.
Prepared standard solutions may offer practical advantages for trace environmental analysis.
Solution concentration, solvent identity, analytical characterization, and storage conditions become key parameters in these applications.
PROCESS CONTROL
Chemical manufacturers can monitor 1-Nitronaphthalene during nitration, reduction, sulfonation, and other conversion processes.
Analytical measurement helps determine reaction completion, residual starting material, isomer distribution, and product purity.
Gas chromatography can distinguish volatile or semivolatile aromatic components in nitration-derived mixtures.
HPLC can also be useful where the downstream products include more polar sulfonated or amino derivatives.
Monitoring residual 1-Nitronaphthalene after reduction provides information about conversion efficiency.
Incomplete reduction can affect downstream amine assay, colour, purification load, and subsequent reaction stoichiometry.
GRADE SELECTION AND PRODUCT SUITABILITY
Assay is a primary purchasing parameter for 1-Nitronaphthalene used in chemical synthesis.
Higher purity improves control of reduction stoichiometry, substitution reactions, purification, and downstream product composition.
Positional-isomer content is particularly important.
2-Nitronaphthalene produces different downstream derivatives and can therefore interfere with processes designed specifically around the 1-substituted structure.
Naphthalene content can also be relevant because unreacted starting material may remain following nitration.
Residual naphthalene changes active-material content and can carry into subsequent reduction or purification stages.
Dinitronaphthalene content may become significant when nitration conditions produce over-nitrated material.
These compounds have different molecular weights, reduction requirements, melting characteristics, and downstream reaction behaviour.
Colour and appearance provide useful supplementary quality information.
A pale yellow crystalline product is characteristic, while unusual darkening can indicate process-related impurities or degradation.
Melting range provides a useful identity and purity parameter.
A defined melting interval near the characteristic range supports evaluation of crystalline product consistency.
Moisture is generally less important chemically than aromatic impurity profile because 1-Nitronaphthalene is hydrophobic, but controlled moisture remains useful for weighing, storage, packaging, and certain downstream processes.
Analytical-reference grades place substantially greater emphasis on characterized purity than bulk intermediate grades.
Chromatographic purity, identity confirmation, and documentation become central when the product is used for calibration or environmental measurement.
FORMULATION AND PROCESS CONSIDERATIONS
The low water solubility of 1-Nitronaphthalene means that most synthetic processing is better suited to organic media, molten handling, or heterogeneous reaction systems.
Aqueous processing generally requires a suitable phase-transfer or suspension strategy when direct dissolution is not possible.
Solvent selection should consider reaction type, operating temperature, product isolation, impurity solubility, and solvent recovery.
The selected solvent should provide adequate mass transfer without introducing unwanted reaction with the nitroaromatic substrate.
Reduction processes require efficient contact between 1-Nitronaphthalene and the reducing system.
Mixing and temperature control affect conversion rate, selectivity, and formation of intermediate nitroso or hydroxylamine species.
Heat removal is important during strongly exothermic chemical transformations.
Nitration and reduction systems should therefore be designed with appropriate reaction-temperature and addition-rate control.
Crystallization can be used to isolate and purify 1-Nitronaphthalene because of its defined melting and solubility behaviour.
Cooling rate, solvent composition, impurity level, and agitation influence crystal size and filtration performance.
Processing near the melting point requires careful temperature management.
Localized solidification can block transfer equipment, while excessive heating can increase vapour generation and thermal stress.
Powder handling should minimize airborne particulate matter.
Enclosed charging and local exhaust ventilation are useful during weighing, sampling, milling, transfer, or repackaging.
QUALITY, SPECIFICATIONS AND DOCUMENTATION
Relevant quality parameters for 1-Nitronaphthalene can include assay, appearance, melting range, moisture, naphthalene content, 2-nitronaphthalene, dinitronaphthalenes, and other aromatic impurities.
The appropriate specification depends on whether the product is intended for reduction, substitution chemistry, research, or analytical use.
Gas chromatography is particularly suitable for determining 1-Nitronaphthalene and related nonionic aromatic impurities.
A chromatographic profile can reveal residual naphthalene, positional isomers, and over-nitrated by-products.
Melting-point analysis provides an additional practical identity and purity check.
Impurities can broaden or depress the characteristic melting range.
Spectroscopic identification can include infrared and mass-spectrometric analysis.
The nitro group produces characteristic infrared absorption, while the mass spectrum provides a useful fingerprint for analytical confirmation.
High-purity analytical material can additionally be characterized by quantitative chromatographic methods.
Accurate purity assignment is particularly important when the compound is used as a calibration standard.
A Certificate of Analysis provides batch-specific results for the selected release parameters.
A Technical Data Sheet provides relevant product characteristics, while the Safety Data Sheet provides hazard, handling, storage, transport, exposure-control, and emergency-response information.
SAFETY AND REGULATORY CONSIDERATIONS
1-Nitronaphthalene is a combustible nitroaromatic solid and should be protected from flames, sparks, hot surfaces, and other uncontrolled ignition sources.
International dangerous-goods transport provisions classify nitronaphthalene as a Class 4.1 flammable solid.
Dust, vapour, and direct contact should be minimized during industrial handling.
1-Nitronaphthalene can cause irritation, and occupational controls should limit inhalation and unnecessary skin or eye exposure.
Experimental toxicology has identified the respiratory system as an important target following significant exposure to 1-Nitronaphthalene.
Effective containment and ventilation are therefore appropriate when the material is heated or handled in operations capable of generating vapour or dust.
Bacterial mutagenicity studies have demonstrated mutagenic activity for 1-Nitronaphthalene.
Workplace practices should consequently emphasize exposure minimization and good industrial hygiene.
Combustion or thermal decomposition can generate nitrogen oxides, carbon monoxide, carbon dioxide, and irritating smoke.
Fire response should use protective equipment appropriate for combustion products from nitroaromatic materials.
Release to the environment should be minimized.
Its hydrophobic aromatic structure promotes interaction with organic matter and environmental solids rather than unrestricted dissolution in water.
FIRST AID
Inhalation: Move the exposed person to fresh air and keep at rest.
Obtain medical attention if coughing, breathing discomfort, headache, dizziness, irritation, or other symptoms develop.
Skin Contact: Remove contaminated clothing and wash affected skin thoroughly with soap and water.
Obtain medical attention if irritation persists or significant exposure has occurred.
Eye Contact: Rinse cautiously with plenty of clean water for several minutes while holding the eyelids open.
Remove contact lenses when easy to do, continue rinsing, and obtain medical attention if irritation persists.
Ingestion: Rinse the mouth and obtain prompt medical advice.
Do not induce vomiting unless directed by qualified medical personnel.
Note to Physicians: Treatment should be based on the route and extent of exposure and the observed clinical condition.
Respiratory effects are particularly relevant following substantial exposure.
HANDLING AND STORAGE
Handling: Avoid breathing 1-Nitronaphthalene dust or vapour and prevent unnecessary skin and eye contact.
Keep the material away from flames, sparks, excessive heat, and incompatible reactive substances.
Ventilation: Provide effective general ventilation and local exhaust ventilation at charging, transfer, sampling, heating, and other points where airborne material may be generated.
Storage: Store 1-Nitronaphthalene in tightly closed containers in a cool, dry, well-ventilated location.
Protect the material from excessive heat, ignition sources, moisture, contamination, and physical damage to packaging.
Incompatibilities: Keep separated from strong oxidizing agents, strong reducing agents, and other highly reactive materials capable of uncontrolled reaction with nitroaromatic compounds.
Packaging: Use clean, dry, chemically compatible packaging suitable for a Class 4.1 solid and capable of preventing product loss, contamination, and exposure during handling.
PACKAGING AND TRANSPORT CONSIDERATIONS
1-Nitronaphthalene is covered by the dangerous-goods transport entry for nitronaphthalene.
The classification reflects its combustible solid-state characteristics.
UN Number: 2538
Proper Shipping Name: Nitronaphthalene
Transport Class: 4.1
Packing Group: III
Packaging and transport arrangements should correspond to the quantity, shipping mode, and dangerous-goods provisions applicable to Class 4.1 materials.
Containers should remain securely closed and protected from ignition sources and physical damage.
Product temperature should be considered when material is shipped or handled close to its melting range.
A package designed for crystalline solid handling may behave differently if the product is exposed to prolonged temperatures above its melting point.
PROCUREMENT CONSIDERATIONS
1-Nitronaphthalene should be purchased according to its intended downstream chemistry.
Reduction to 1-naphthylamine, sulfonation, further nitration, specialty synthesis, and analytical use place different emphasis on assay and impurity control.
CAS Number 86-57-7 should be included clearly in purchasing documentation.
This distinction is particularly important because 2-nitronaphthalene is a separate positional isomer and cannot automatically replace 1-Nitronaphthalene.
Chemical-intermediate applications should consider assay, residual naphthalene, 2-nitronaphthalene content, dinitronaphthalene content, moisture, appearance, and melting range.
These parameters influence reaction stoichiometry, product-isomer profile, purification requirements, and yield.
Reduction processes place particular importance on total nitroaromatic composition.
An impurity containing an additional nitro group consumes more reducing capacity, while the wrong positional isomer produces an undesired amine.
Sulfonation and dye-intermediate applications benefit from tight isomer control because positional substitution determines the identity of the final naphthalene derivative.
Even structurally similar impurities can generate colorants with different shade or processing behaviour.
Analytical applications require a different grade-selection approach.
High chromatographic purity, defined identity, appropriate packaging quantity, and analytical documentation are more important than bulk handling characteristics.
Physical form should also be considered.
Crystals or powder may provide convenient solid charging, while controlled molten transfer can be appropriate for integrated manufacturing processes equipped for heated handling.
Package size should correspond to batch consumption, storage conditions, dust-control infrastructure, and dangerous-goods handling capability.
Avoiding unnecessary repackaging can reduce contamination and occupational exposure.
Ataman Kimya can support enquiries for 1-Nitronaphthalene concerning purity, positional-isomer requirements, chemical specifications, analytical documentation, packaging, dye-intermediate applications, specialty synthesis, research use, and supply requirements.
For product and procurement information, contact Ataman Kimya at +90 216 577 10 10 or [info@atamankimya.com](mailto:info@atamankimya.com).
