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4-Nitrophenetole is a para-substituted aromatic nitro ether commonly known as p-nitrophenetole or 1-ethoxy-4-nitrobenzene.
4-Nitrophenetole is normally supplied as a pale-yellow to yellow crystalline solid with a melting point near 59°C.
4-Nitrophenetole is used primarily as an intermediate for p-phenetidine and downstream dyes, antioxidants, pharmaceutical intermediates, specialty chemicals, and analytical reference materials.
CAS Number: 100-29-8
EC Number: 202-837-9
Molecular Formula: C₈H₉NO₃
Molecular Weight: 167.16 g/mol
SYNONYMS
1-Ethoxy-4-nitrobenzene, Benzene, 1-ethoxy-4-nitro-, p-Nitrophenetole, para-Nitrophenetole, 4-Nitrophenetole, p-Ethoxynitrobenzene, para-Ethoxynitrobenzene, 4-Ethoxynitrobenzene, 1-Nitro-4-ethoxybenzene, 4-Nitro-1-ethoxybenzene, Ethyl p-nitrophenyl ether, Ethyl 4-nitrophenyl ether, 4-Nitrophenyl ethyl ether, p-Nitrophenyl ethyl ether, para-Nitrophenyl ethyl ether, p-Nitrophenetol, 4-Nitrophenetol, Phenetole, p-nitro-, Phenetole, 4-nitro-, para-Nitrophenetol, 4-Ethoxy-1-nitrobenzene, 1-Ethoxy-4-nitro-benzene, p-Nitroethyl phenyl ether, para-Nitroethyl phenyl ether, p-Nitrobenzene ethyl ether, 4-Nitrobenzene ethyl ether, Ethoxy-p-nitrobenzene, para-Ethoxy nitrobenzene, Nitroaromatic Ether, para-Substituted Nitroaromatic Ether, Aromatic Nitro Ether, Ethoxy-Substituted Nitrobenzene, p-Phenetidine Precursor, 4-Ethoxyaniline Precursor, Dye-Intermediate Precursor, Fine-Chemical Intermediate, Organic-Synthesis Intermediate, Analytical-Grade 4-Nitrophenetole, Reagent-Grade 4-Nitrophenetole, Synthesis-Grade 4-Nitrophenetole, High-Purity 4-Nitrophenetole, Technical-Grade 4-Nitrophenetole, Crystalline 4-Nitrophenetole, 4-Nitrophenetole Analytical Standard, CAS 100-29-8, EC 202-837-9, PubChem CID 7495, NSC 9812, RTECS DA0600000, MFCD00007330, UNII O0A69I1MCU, C₈H₉NO₃, C₂H₅OC₆H₄NO₂, NWPKEYHUZKMWKJ-UHFFFAOYSA-N
APPLICATIONS
4-Nitrophenetole serves as the principal nitroaromatic precursor for producing p-phenetidine through selective reduction of the nitro group.
4-Nitrophenetole supports catalytic hydrogenation processes that convert the para nitro group into a primary amino group while retaining the ethoxy substituent.
4-Nitrophenetole enables production of high-purity 4-ethoxyaniline after reduction, catalyst separation, purification, and distillation.
4-Nitrophenetole requires low levels of positional isomers and azoxy impurities when the resulting p-phenetidine is intended for performance-sensitive synthesis.
4-Nitrophenetole functions as an intermediate in production routes leading from p-phenetidine to ethoxyquin.
4-Nitrophenetole provides the para-ethoxyphenyl structure incorporated into the antioxidant’s quinoline framework.
4-Nitrophenetole supports manufacture of intermediates historically used to protect oxidation-sensitive oils and feed components.
4-Nitrophenetole itself should not be represented as an antioxidant because reduction and additional downstream synthesis are required before the final functional compound is obtained.
4-Nitrophenetole serves as an upstream intermediate in historical synthesis routes associated with phenacetin.
4-Nitrophenetole is first converted into p-phenetidine before acylation yields the corresponding acetanilide derivative.
4-Nitrophenetole supports chemical-history, impurity-reference, and controlled pharmaceutical-process research involving para-ethoxy aromatic compounds.
4-Nitrophenetole does not possess the identity or pharmacological status of the downstream pharmaceutical compound.
4-Nitrophenetole functions as a precursor for phenocoll-related and p-phenetylurea-related chemical intermediates.
4-Nitrophenetole enables preparation of the required para-ethoxy aromatic amine through nitro-group reduction.
4-Nitrophenetole supports urea, carbamate, amide, and related derivatization chemistry after conversion to p-phenetidine.
4-Nitrophenetole requires every downstream derivative to receive an independent identity, purity, toxicological, and regulatory assessment.
4-Nitrophenetole finds application as an upstream intermediate in the manufacture of azo dyes and related colorants.
4-Nitrophenetole is reduced to p-phenetidine, which can subsequently undergo diazotization and azo-coupling reactions.
4-Nitrophenetole contributes a para-ethoxy substituent that can influence shade, electron distribution, solubility, and substrate affinity in derived colorants.
4-Nitrophenetole supports dye-intermediate production where positional-isomer purity and control of colored azoxy by-products are particularly important.
4-Nitrophenetole serves as an intermediate for ice dyes, disperse dyes, solvent dyes, and other specialty colorant research after reduction or further transformation.
4-Nitrophenetole provides a defined para-substituted aromatic platform that can be converted into amino, diazonium, amide, and urea derivatives.
4-Nitrophenetole supports synthesis of chromophores intended for textiles, polymers, inks, coatings, and analytical indicators.
4-Nitrophenetole requires the final dye or pigment to be assessed separately for color performance, migration, light stability, exposure, and environmental behavior.
4-Nitrophenetole functions as a fine-chemical building block in medicinal-chemistry research.
4-Nitrophenetole supplies a protected aromatic amino precursor that can be revealed by reduction at a selected stage of synthesis.
4-Nitrophenetole enables preparation of para-ethoxyphenyl amides, ureas, sulfonamides, carbamates, imines, and heterocyclic derivatives.
4-Nitrophenetole supports route development where the nitro group provides chemical stability during transformations that might be incompatible with a free aniline.
4-Nitrophenetole serves as a nitro-group reduction substrate in heterogeneous and homogeneous catalyst screening.
4-Nitrophenetole enables comparison of palladium, platinum, nickel, iron, and other reduction systems under controlled conditions.
4-Nitrophenetole supports measurement of conversion, p-phenetidine selectivity, azoxy-compound formation, dehalogenation risk, and ether stability.
4-Nitrophenetole provides commercially relevant process information when catalyst testing uses representative impurity, solvent, pressure, and temperature conditions.
4-Nitrophenetole functions as a model compound in chemoselective hydrogenation research.
4-Nitrophenetole contains a reducible nitro group alongside an aromatic ether that should normally remain intact during selective processing.
4-Nitrophenetole supports evaluation of whether reaction conditions generate hydroxylamine, azo, azoxy, dealkylated, or ring-hydrogenated by-products.
4-Nitrophenetole enables catalyst performance to be linked directly with downstream p-phenetidine purity.
4-Nitrophenetole serves as a product standard in studies of nucleophilic aromatic substitution involving 4-chloronitrobenzene and ethanol.
4-Nitrophenetole forms when ethoxide displaces chloride from the activated para-nitrochlorobenzene ring.
4-Nitrophenetole supports evaluation of alkali-metal hydroxide concentration, phase-transfer catalyst loading, temperature, pressure, and ethanol feed rate.
4-Nitrophenetole enables process engineers to quantify conversion while monitoring 4-nitrophenol, unreacted chloronitrobenzene, and azoxy by-products.
4-Nitrophenetole functions as a target product in phase-transfer-catalyzed etherification research.
4-Nitrophenetole supports comparison of quaternary ammonium salts, crown ethers, alkali-metal bases, and biphasic reaction conditions.
4-Nitrophenetole enables high conversion at moderate temperatures when mass transfer and base addition are properly controlled.
4-Nitrophenetole requires reaction design that prevents accumulation of flammable ethanol–oxygen mixtures during oxygen-assisted processing.
4-Nitrophenetole serves as a reference product in process studies designed to suppress azo and azoxy impurity formation.
4-Nitrophenetole can undergo or accompany reductive coupling reactions when unsuitable conditions promote conversion of nitroaromatic intermediates into colored by-products.
4-Nitrophenetole production benefits from controlled oxygen availability, reactant feed, mixing, and reaction temperature.
4-Nitrophenetole purity is especially important when the material is subsequently reduced for dye-intermediate manufacture.
4-Nitrophenetole finds application as a precursor in alternative p-phenetidine manufacturing routes based on catalytic hydrogenation.
4-Nitrophenetole supports batch and continuous reduction using suitable hydrogenation catalysts and liquid-phase processing.
4-Nitrophenetole enables integration of reduction, catalyst filtration, solvent recovery, and product distillation into an industrial process.
4-Nitrophenetole feed quality influences catalyst life, hydrogen consumption, filtration load, product color, and final amine assay.
4-Nitrophenetole functions as an intermediate in the preparation of para-ethoxyphenyl isocyanates.
4-Nitrophenetole is first reduced to p-phenetidine before controlled carbonylation or phosgenation forms the corresponding isocyanate.
4-Nitrophenetole supports downstream synthesis of substituted ureas, carbamates, and functional polymer additives.
4-Nitrophenetole requires highly controlled processing whenever toxic carbonylating or phosgenating reagents are used.
4-Nitrophenetole serves as an upstream raw material for para-ethoxyphenyl amide and sulfonamide intermediates.
4-Nitrophenetole provides the required aromatic structure after conversion into the corresponding primary amine.
4-Nitrophenetole supports preparation of fine chemicals whose polarity and molecular recognition are modified by the ethoxy group.
4-Nitrophenetole does not establish the safety, efficacy, or regulatory status of the resulting amide or sulfonamide.
4-Nitrophenetole functions as a precursor for Schiff bases and imine-containing research compounds.
4-Nitrophenetole is reduced to p-phenetidine, which can condense with aldehydes and ketones.
4-Nitrophenetole supports synthesis of ligands, analytical derivatives, catalysts, and functional organic molecules.
4-Nitrophenetole enables investigation of how a para ethoxy group affects imine stability, electronic behavior, and metal coordination.
4-Nitrophenetole finds application as a precursor in heterocyclic-chemistry research.
4-Nitrophenetole provides p-phenetidine after reduction for cyclization with carbonyl, nitrile, isocyanate, and sulfur-containing reagents.
4-Nitrophenetole supports preparation of nitrogen-containing rings bearing a para-ethoxyphenyl substituent.
4-Nitrophenetole requires each heterocyclic derivative to be characterized independently because its properties cannot be inferred from the nitro ether.
4-Nitrophenetole serves as an analytical reference material in gas chromatography and liquid chromatography.
4-Nitrophenetole supports measurement of reaction conversion, product assay, positional isomers, residual chloronitrobenzene, and p-nitrophenol.
4-Nitrophenetole enables reverse-phase chromatographic separation through its moderate hydrophobicity and strong ultraviolet response.
4-Nitrophenetole requires traceable purity and controlled moisture when used for quantitative analytical calibration.
4-Nitrophenetole functions as a reference compound for infrared and electron-ionization mass spectrometry.
4-Nitrophenetole provides established molecular identity, fragmentation, and vibrational data for confirmation of laboratory and industrial samples.
4-Nitrophenetole supports comparison with 2-nitrophenetole, 3-nitrophenetole, p-nitrophenol, p-phenetidine, and related process impurities.
4-Nitrophenetole enables analytical laboratories to verify chromatographic peak identity through orthogonal spectral methods.
4-Nitrophenetole serves as a reference substance in crystallographic and solid-state studies.
4-Nitrophenetole provides a comparatively simple para-substituted aromatic molecule containing both an electron-donating ethoxy group and an electron-withdrawing nitro group.
4-Nitrophenetole supports investigation of crystal packing, molecular planarity, dipolar interactions, and melting behavior.
4-Nitrophenetole enables comparison between methoxy-, ethoxy-, and higher-alkoxy-substituted nitrobenzenes.
4-Nitrophenetole functions as a model nitroaromatic compound in environmental and biodegradation research.
4-Nitrophenetole supports evaluation of microbial transformation, reduction, ether cleavage, adsorption, and aquatic toxicity.
4-Nitrophenetole provides a neutral aromatic ether whose environmental behavior differs from ionizable p-nitrophenol.
4-Nitrophenetole requires containment because current safety information classifies it as toxic to aquatic life with long-lasting effects.
4-Nitrophenetole serves as a target analyte in research concerning nitroaromatic wastewater and process-effluent treatment.
4-Nitrophenetole supports comparison of adsorption, catalytic reduction, oxidation, biological treatment, and solvent-recovery methods.
4-Nitrophenetole enables measurement of parent-compound disappearance and formation of p-phenetidine, p-nitrophenol, or other transformation products.
4-Nitrophenetole requires analytical confirmation that treatment achieves genuine removal rather than transfer into sludge, air, or another phase.
4-Nitrophenetole functions as a test compound in organic-solvent extraction and partitioning studies.
4-Nitrophenetole shows moderate affinity for nonpolar phases because of its aromatic ether structure.
4-Nitrophenetole supports method development involving acetonitrile, alcohols, ketones, aromatic solvents, and chromatographic mobile phases.
4-Nitrophenetole requires solvent selection that accounts for crystallization near room temperature and the intended recovery method.
4-Nitrophenetole finds application in organic-reaction teaching laboratories as an example of aromatic ether formation.
4-Nitrophenetole demonstrates nucleophilic aromatic substitution made possible by activation of a halogenated aromatic ring with a para nitro group.
4-Nitrophenetole supports instruction in phase-transfer catalysis, recrystallization, melting-point analysis, chromatography, and spectroscopy.
4-Nitrophenetole requires professional supervision, adequate ventilation, eye protection, and controlled waste collection.
4-Nitrophenetole serves as an educational reduction substrate for demonstrating conversion of an aromatic nitro group into an aniline.
4-Nitrophenetole enables comparison of catalytic hydrogenation, metal–acid reduction, and other selective reduction systems.
4-Nitrophenetole supports analysis of reaction intermediates and colored azo or azoxy side products.
4-Nitrophenetole should be handled only at laboratory scale under procedures appropriate for nitroaromatic solids and flammable reducing systems.
4-Nitrophenetole functions as a quality-control standard in p-phenetidine production.
4-Nitrophenetole enables measurement of unreacted feed remaining after catalytic reduction.
4-Nitrophenetole supports determination of conversion efficiency, catalyst performance, and downstream purification requirements.
4-Nitrophenetole residual limits should be defined according to the specification and intended use of the final p-phenetidine.
4-Nitrophenetole serves as an impurity reference in processes involving p-nitrochlorobenzene, p-nitrophenol, or para-ethoxy aromatic intermediates.
4-Nitrophenetole supports method validation for related-substance testing and process troubleshooting.
4-Nitrophenetole enables identification of unintended ethoxylation or incomplete downstream reduction.
4-Nitrophenetole requires chromatographic methods capable of separating closely related positional and functional-group analogues.
4-Nitrophenetole functions as a fine-chemical inventory intermediate for custom synthesis.
4-Nitrophenetole offers a stable crystalline nitro precursor that can be stored and transported more conveniently than some reactive downstream amines.
4-Nitrophenetole supports staged manufacturing in which reduction is performed immediately before amine derivatization.
4-Nitrophenetole requires storage conditions that preserve color, assay, crystal form, and freedom from oxidizing contamination.
4-Nitrophenetole serves as a molecular probe in studies of substituent effects on aromatic electronic structure.
4-Nitrophenetole combines an electron-donating ethoxy group with an electron-withdrawing nitro group in a para arrangement.
4-Nitrophenetole supports spectroscopic and computational comparison of donor–acceptor interactions within a single aromatic ring.
4-Nitrophenetole enables correlation of substitution pattern with polarity, ultraviolet absorption, reduction behavior, and chromatographic retention.
4-Nitrophenetole functions as a substrate in research on nitroaromatic deoxygenation, denitration, and reductive coupling.
4-Nitrophenetole allows researchers to evaluate whether the aromatic ether remains intact under aggressive catalytic conditions.
4-Nitrophenetole supports detection of nitroso, hydroxylamine, azo, azoxy, and aniline intermediates.
4-Nitrophenetole requires reaction-hazard assessment because some nitro-compound reductions can be strongly exothermic.
4-Nitrophenetole finds application in preparative chromatographic method development.
4-Nitrophenetole can be separated from more polar p-nitrophenol and less polar chlorinated or azo impurities using suitable stationary and mobile phases.
4-Nitrophenetole supports recovery of high-purity fractions for analytical standards and reaction studies.
4-Nitrophenetole requires crystallization and solvent-removal conditions that prevent contamination and thermal discoloration.
4-Nitrophenetole serves as a reference compound in National Toxicology Program chemical-effects databases.
4-Nitrophenetole supports retrieval and comparison of historical toxicological test information under its registry identity.
4-Nitrophenetole enables researchers to connect test data with CAS Number 100-29-8 and the systematic name 1-ethoxy-4-nitrobenzene.
4-Nitrophenetole should be assessed using the complete study design rather than isolated toxicity values.
4-Nitrophenetole functions as a process-safety model for exothermic aromatic etherification.
4-Nitrophenetole production studies support evaluation of base charging, oxygen concentration, pressure control, agitation, and emergency cooling.
4-Nitrophenetole enables identification of operating conditions that suppress unwanted reductive coupling.
4-Nitrophenetole process scale-up requires calorimetry and gas-phase flammability assessment before oxygen-assisted operation.
4-Nitrophenetole serves as a reference in studies of alkoxy-group stability during nitroaromatic reduction.
4-Nitrophenetole supports comparison of hydrogenolysis, dealkylation, ring reduction, and selective amino-group formation.
4-Nitrophenetole provides a practical substrate for optimizing catalyst selectivity toward p-phenetidine.
4-Nitrophenetole performance should be evaluated with representative process impurities and recycled solvent.
4-Nitrophenetole functions as an intermediate in custom synthesis of para-ethoxyphenyl functional materials.
4-Nitrophenetole enables introduction of amino functionality at a late synthetic stage through controlled reduction.
4-Nitrophenetole supports preparation of research compounds for coatings, polymers, electronics, sensors, and molecular recognition.
4-Nitrophenetole requires application-specific assessment because the final material’s properties depend on all structural components.
4-Nitrophenetole finds application as a comparative standard for positional nitrophenetole isomers.
4-Nitrophenetole supports chromatographic differentiation from 2-nitrophenetole and 3-nitrophenetole.
4-Nitrophenetole enables investigation of how para substitution affects melting point, molecular symmetry, and reduction selectivity.
4-Nitrophenetole provides a defined reference for impurity profiling in industrial etherification processes.
4-Nitrophenetole serves as a raw material for p-phenetidine-based dye and fine-chemical production.
4-Nitrophenetole supports controlled manufacture where high assay, low p-nitrophenol content, and low azoxy impurity levels improve downstream consistency.
DESCRIPTION
4-Nitrophenetole is the common name for the compound systematically identified as 1-ethoxy-4-nitrobenzene.
4-Nitrophenetole is identified by CAS Number 100-29-8 and EC Number 202-837-9.
4-Nitrophenetole has the molecular formula C₈H₉NO₃.
4-Nitrophenetole has a molecular weight of approximately 167.16 g/mol.
Structurally, 4-Nitrophenetole contains one ethoxy group and one nitro group attached to a benzene ring.
The two substituents occupy para or 1,4 positions relative to each other.
The ethoxy group donates electron density to the aromatic system through resonance.
The nitro group withdraws electron density through inductive and resonance effects.
The para arrangement gives 4-Nitrophenetole a comparatively symmetrical molecular structure.
The compound contains three oxygen atoms, with one in the ether group and two in the nitro group.
4-Nitrophenetole has no hydrogen-bond-donor group.
The ether and nitro oxygen atoms function as hydrogen-bond acceptors.
4-Nitrophenetole normally appears as a pale-yellow, yellow, or variably colored crystalline powder or solid.
High-purity material has a representative melting point of approximately 59°C.
Commercial specifications commonly give a melting range near 57–61°C.
Color can vary from nearly white through yellow, orange, or darker shades depending on purity and storage history.
4-Nitrophenetole can soften or melt in warm storage areas because its melting point is only moderately above ordinary room temperature.
The solid may recrystallize into a compact mass after heating and cooling.
Repeated uncontrolled melting can alter particle size, handling properties, and color.
Temperature-controlled storage helps preserve a free-flowing crystalline form.
4-Nitrophenetole has a normal boiling point reported near 556.2 K, corresponding to approximately 283°C.
A reduced-pressure boiling point near 112–115°C at approximately 3 mmHg is also reported.
Vacuum processing therefore permits distillation at substantially lower temperatures than atmospheric operation.
Prolonged high-temperature exposure should be minimized to reduce decomposition and color formation.
4-Nitrophenetole has low volatility as a crystalline solid under normal ambient conditions.
Vapor exposure becomes more relevant when the material is molten, distilled, sprayed, or handled over large heated surfaces.
Dry handling can generate airborne crystalline dust.
Local exhaust ventilation is appropriate at weighing, charging, grinding, and packaging points.
4-Nitrophenetole is only slightly compatible with water in its neutral molecular form.
Its aromatic ring and ethoxy group give the molecule significant organic-phase affinity.
The compound is more compatible with many alcohols, ketones, ethers, aromatic solvents, and chromatographic organic mobile phases.
A reported log P value near 2.5 is consistent with moderate hydrophobicity.
4-Nitrophenetole is a neutral nitroaromatic ether rather than an ionizable phenol under ordinary conditions.
It does not form a simple water-soluble salt through routine neutralization.
Strong acidic conditions can protonate ether or nitro oxygen atoms transiently but do not create a stable ordinary aqueous salt.
Process extraction therefore depends mainly on solvent partitioning, crystallization, and conversion into other functional groups.
4-Nitrophenetole crude product can contain p-nitrophenol, 4-chloronitrobenzene, positional isomers, azo compounds, azoxy compounds, solvent, and inorganic residues.
Colored azoxy impurities can impair appearance and p-phenetidine quality.
Purification may involve phase separation, washing, crystallization, filtration, solvent removal, and vacuum distillation.
Polymerized or highly colored residues may accumulate in high-temperature equipment.
4-Nitrophenetole quality control commonly includes appearance, assay, melting range, moisture, and chromatographic purity.
Gas chromatography can quantify volatile and semivolatile organic impurities.
Liquid chromatography can separate 4-Nitrophenetole from p-nitrophenol and less volatile colored by-products.
Nuclear magnetic resonance and infrared spectroscopy can confirm the ethoxy and nitro functional groups.
4-Nitrophenetole has established infrared and electron-ionization mass spectra in authoritative reference databases.
These spectra support identification of commercial material and reaction products.
The molecular ion corresponds to the nominal molecular mass of the compound.
Fragmentation can reflect cleavage of the ethoxy group and transformations associated with the nitro-substituted aromatic ring.
4-Nitrophenetole has a crystalline structure influenced by its para substitution pattern and molecular dipole.
The ethoxy group retains rotational flexibility around the oxygen–carbon bonds.
The nitro group is strongly conjugated with the aromatic ring, although steric and crystal-packing effects can influence exact planarity.
Solid-state purity and crystal history can affect observed melting behavior.
4-Nitrophenetole is chemically stable under ordinary controlled storage conditions.
Strong oxidizing agents should be avoided.
Powerful reducing agents react with the nitro group and can generate heat.
Strong acids, strong bases, and reactive metals should be evaluated before intentional process contact.
4-Nitrophenetole is an organic combustible solid.
Heating to decomposition can generate nitrogen oxides, carbon monoxide, carbon dioxide, smoke, and irritating organic fumes.
Molten material can spread contamination more readily than the crystalline solid.
Firefighting measures should follow the current grade-specific Safety Data Sheet.
Available commercial hazard information identifies 4-Nitrophenetole as potentially harmful if swallowed.
The same information classifies the substance as toxic to aquatic life with long-lasting effects.
Classification can vary with jurisdiction and data source.
The latest regional classification and supplied Safety Data Sheet should therefore determine labeling and protective measures.
Historical toxicological databases report animal acute-toxicity and mutation-test information for 4-Nitrophenetole.
Individual numerical results should be interpreted only with their original study methods, purity, routes, and observation periods.
Historical test records do not replace a modern regulatory assessment.
Worker exposure should be minimized regardless of the comparatively limited public dataset.
Contact with 4-Nitrophenetole dust may cause mechanical discomfort to the eyes, skin, or respiratory tract.
Molten material can additionally cause thermal injury.
Ingestion should be prevented because harmful effects are possible.
Contaminated work clothing should be removed and cleaned before reuse.
4-Nitrophenetole has moderate organic-phase affinity and should not be released into wastewater or natural waters.
Its aquatic-hazard classification requires prevention of long-term environmental contamination.
Spills should be collected as a solid or compatible absorbent waste rather than washed into drains.
Waste treatment should consider the nitroaromatic structure and possible formation of aromatic amine reduction products.
4-Nitrophenetole is listed in European chemical inventories under EC Number 202-837-9.
Its presence in an inventory does not itself authorize every industrial, consumer, food, feed, pharmaceutical, or pesticidal use.
Current national and regional obligations should be checked before manufacture, import, sale, or use.
Application-specific legislation may impose additional impurity, worker-exposure, or environmental requirements.
4-Nitrophenetole is normally stored as a dry crystalline intermediate.
Cool and dark storage helps reduce discoloration and physical softening.
Some technical product information recommends storage below approximately 15°C.
Actual storage temperature should follow the current supplied specification.
4-Nitrophenetole containers should be protected from heat, direct sunlight, oxidizing chemicals, and moisture contamination.
The container should remain tightly closed to prevent dust release and foreign-material ingress.
Packaging should resist the selected product form and storage temperature.
Partially melted material should be allowed to solidify under controlled conditions before mechanical handling.
4-Nitrophenetole purity is especially important when the material is reduced to p-phenetidine.
Chlorinated starting material can affect catalyst and downstream product quality.
p-Nitrophenol can alter acidity and purification behavior.
Azo and azoxy impurities can contribute strong color even at relatively low concentrations.
4-Nitrophenetole assay is commonly determined by gas chromatography.
Melting range provides a useful supplementary purity indicator.
A broadened or depressed melting range can indicate impurities, mixed crystal forms, residual solvent, or partial melting history.
The certificate of analysis should define acceptance criteria for the intended synthesis or analytical application.
PROPERTIES
Chemical Name: 4-Nitrophenetole
Preferred IUPAC Name: 1-Ethoxy-4-nitrobenzene
Registry Name: Benzene, 1-ethoxy-4-nitro-
Common Name: p-Nitrophenetole
Alternative Common Name: p-Ethoxynitrobenzene
CAS Number: 100-29-8
EC Number: 202-837-9
PubChem CID: 7495
NSC Number: 9812
RTECS Number: DA0600000
UNII: O0A69I1MCU
MDL Number: MFCD00007330
Molecular Formula: C₈H₉NO₃
Condensed Structural Formula: C₂H₅OC₆H₄NO₂
Molecular Weight: 167.16 g/mol
Exact Molecular Weight: Approximately 167.0582 Da
InChIKey: NWPKEYHUZKMWKJ-UHFFFAOYSA-N
Chemical Family: Nitroaromatic ethers
Chemical Classification: Para-substituted aromatic nitro ether
Functional Groups: Aromatic ether and nitro group
Aromatic Substitution Pattern: Para or 1,4-substitution
Hydrogen-Bond Donors: 0
Hydrogen-Bond Acceptors: 3
Physical State at 20°C: Solid
Appearance: Pale-yellow to yellow crystalline powder or crystals
Commercial Appearance Range: White to yellow, orange, or darker crystalline material depending on purity
Melting Point: Approximately 59°C
Typical Specification Melting Range: Approximately 57–61°C
Normal Boiling Point: Approximately 283°C
Reduced-Pressure Boiling Point: Approximately 112–115°C at 3 mmHg
Volatility: Low at ambient temperature
Water Solubility: Slight; grade-specific experimental value should be confirmed
Organic-Solvent Compatibility: Compatible with many alcohols, ketones, ethers, aromatic solvents, and chromatographic organic phases
Reported Log Pow: Approximately 2.5
Primary Industrial Function: Fine-chemical intermediate
Principal Downstream Product: p-Phenetidine or 4-ethoxyaniline
Principal Downstream Applications: Dyes, antioxidants, pharmaceutical intermediates, urea derivatives, carbamates, amides, and specialty chemicals
Primary Production Route: Ethoxylation of 4-chloronitrobenzene
Alternative Production Route: Ethylation of p-nitrophenol or p-nitrophenolate
Primary Reduction Reaction: Conversion of the nitro group to a primary amino group
Important Process Impurities: p-Nitrophenol, 4-chloronitrobenzene, positional isomers, azo compounds, and azoxy compounds
Primary Analytical Methods: Gas chromatography, liquid chromatography, infrared spectroscopy, mass spectrometry, and nuclear magnetic resonance
Available Hazard Statement: May be harmful if swallowed
Aquatic Hazard Statement: Toxic to aquatic life with long-lasting effects
Combustibility: Combustible organic solid
Dust Exposure Potential: Possible during dry charging, grinding, and packaging
Molten-Material Hazard: Thermal burns and increased surface contamination
Chemical Stability: Stable under recommended cool and controlled storage conditions
Incompatible Materials: Strong oxidizing agents, powerful reducing agents, and other reactive materials identified in the current Safety Data Sheet
FIRST AID
Inhalation:
Move the affected person to fresh air.
Keep the person at rest in a position comfortable for breathing.
Avoid further exposure to 4-Nitrophenetole dust, vapor, aerosol, smoke, or thermal-decomposition fumes.
Obtain medical attention if coughing, sore throat, breathing discomfort, headache, dizziness, weakness, or other symptoms develop or persist.
Skin Contact:
Remove contaminated clothing and footwear.
Brush away loose dry material carefully without dispersing dust.
Wash the affected skin thoroughly with soap and plenty of water.
Cool skin exposed to molten 4-Nitrophenetole with clean running water and do not forcibly remove solidified material.
Obtain medical attention if redness, irritation, pain, blistering, or thermal injury occurs.
Eye Contact:
Rinse the eyes immediately with plenty of clean, gently flowing water.
Hold the eyelids open to ensure complete irrigation.
Remove contact lenses when present and easy to do, then continue rinsing.
Continue rinsing for at least 15 minutes.
Obtain medical attention if pain, redness, tearing, blurred vision, or irritation persists.
Ingestion:
Rinse the mouth thoroughly with water.
Do not induce vomiting unless directed by qualified medical personnel or a poison center.
Never give anything by mouth to an unconscious, drowsy, or convulsing person.
Obtain prompt medical attention because 4-Nitrophenetole may be harmful if swallowed.
Provide the current Safety Data Sheet and product label to medical personnel.
Note to Physicians:
No substance-specific antidote should be assumed.
Provide supportive care and treat according to the patient’s symptoms and clinical condition.
Assess respiratory, neurological, gastrointestinal, hepatic, renal, and hematological status following substantial exposure.
Consider that aromatic nitro compounds and reduction products can produce delayed systemic effects even when early symptoms are limited.
Use current poison-center guidance and the grade-specific Safety Data Sheet as the primary medical references.
HANDLING AND STORAGE
Handling:
Handle 4-Nitrophenetole in accordance with good industrial-hygiene and nitroaromatic-chemical procedures.
Review the current technical specification and Safety Data Sheet before opening, sampling, melting, transferring, or processing the material.
Avoid unnecessary contact with the skin, eyes, and clothing.
Do not breathe dust, vapor, aerosol, smoke, or thermal-decomposition fumes.
Use enclosed charging, weighing, melting, reaction, filtration, and packaging systems wherever reasonably practicable.
Avoid pouring, grinding, sweeping, or pneumatic-transfer methods that generate uncontrolled dust.
Use clean, dry, and chemically compatible equipment for sampling, weighing, transfer, and reaction.
Heat solid material gradually and indirectly when melting is required.
Avoid localized overheating and prolonged molten holding.
Keep 4-Nitrophenetole away from strong oxidizing agents, uncontrolled reducing agents, flames, sparks, and hot surfaces.
Wash the hands, face, and exposed skin thoroughly after handling.
Do not eat, drink, or smoke in areas where 4-Nitrophenetole is processed.
Keep containers tightly closed when the material is not being sampled or transferred.
Ventilation:
Provide effective general ventilation in storage and processing areas.
Use local exhaust ventilation at weighing stations, bag-emptying points, grinders, reactors, filters, dryers, and packaging equipment.
Capture dust, vapor, aerosol, and decomposition fumes at the source.
Provide additional ventilation when 4-Nitrophenetole is heated, melted, distilled, sprayed, or processed in confined equipment.
Use dust-collection equipment suitable for organic combustible particulate material where required.
Prevent recirculation of contaminated air unless it has been adequately filtered.
Use suitable particulate respiratory protection when engineering controls cannot adequately limit dust exposure.
Use combination or supplied-air respiratory protection when heated vapor, smoke, or unknown concentrations may be present.
Select respiratory protection through a documented occupational-exposure and hazard assessment.
Inspect and maintain ventilation and dust-collection systems regularly.
Storage:
Store 4-Nitrophenetole in tightly closed and correctly labeled containers.
Keep the material in a cool, dry, dark, secure, and well-ventilated location.
Follow the current grade documentation where storage below approximately 15°C is recommended.
Protect 4-Nitrophenetole from direct sunlight, excessive heat, moisture, contamination, and physical damage.
Keep 4-Nitrophenetole separated from strong oxidizing agents, powerful reducing agents, and incompatible reactive chemicals.
Keep the material away from flames, sparks, hot surfaces, and uncontrolled heating.
Use moisture-resistant and chemically compatible packaging.
Prevent water, dirt, metals, oxidants, reducing chemicals, and process residues from entering opened containers.
Reseal partially used containers immediately after sampling or transfer.
Use first-in, first-out stock rotation within the applicable shelf life.
Inspect stored material for discoloration, caking, partial melting, damaged packaging, contamination, or unusual odor before use.
Prevent repeated uncontrolled melting and recrystallization during storage.
Spill and Leak Procedures:
Restrict access to the affected area and remove unnecessary personnel.
Eliminate ignition sources when this can be done safely.
Provide effective ventilation before beginning recovery operations.
Wear suitable gloves, protective clothing, eye protection, and particulate respiratory protection.
Avoid dry sweeping, compressed-air cleaning, or other methods that disperse crystalline dust.
Carefully collect dry material with a suitable hazardous-dust vacuum or low-dust mechanical method.
Allow molten material to cool and solidify when this can be done safely.
Do not touch hot or solidifying material with unprotected skin.
Place recovered material in tightly closed, chemically compatible, and correctly labeled containers.
Prevent 4-Nitrophenetole from entering drains, sewers, soil, groundwater, or surface water.
Collect contaminated absorbents, disposable equipment, and cleaning residues for authorized disposal.
Clean the affected surface after bulk recovery without generating uncontrolled wastewater.
Dispose of recovered material through an authorized chemical-waste route.
Handling Precautions:
Wear chemical-resistant protective gloves selected from documented compatibility and permeation data.
Use safety spectacles with side protection or tightly fitting chemical goggles.
Wear a face shield in addition to goggles where molten-material or solution splashing is reasonably foreseeable.
Use protective clothing and closed chemical-resistant footwear.
Use heat-resistant gloves, sleeves, and suitable protective clothing when handling molten material.
Provide accessible eyewash and emergency-shower equipment near major handling locations.
Use suitable particulate respiratory protection for dusty operations.
Use respiratory protection appropriate to organic vapor and decomposition fumes during heated or emergency operations.
Ground and bond conductive equipment where the process assessment identifies static or combustible-dust hazards.
Inspect containers, heating systems, pumps, hoses, seals, ventilation equipment, and dust collectors before use.
Do not mix 4-Nitrophenetole with strong oxidizing agents or powerful reducing systems without a documented reaction-hazard assessment.
Control temperature, hydrogen pressure, catalyst addition, and heat removal during nitro-group reduction.
Control oxygen concentration and ignition sources during oxygen-assisted etherification processes.
Prevent environmental release during production, transfer, storage, cleaning, transport, and waste handling.
Review the current technical specification, Safety Data Sheet, certificate of analysis, occupational requirements, environmental regulations, and transport rules before use.
