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4-Nitrophenol
P-NITROPHENOL · HONP · PARA-NITROPHENOL · p-Nitrofenol · 4-Nitrofenol · 4-HYDROXYNITROBENZENE · 1-Hydroxy-4-nitrobenzene · 4-nitro-pheno
Identifikatoren & physikalische Daten
| CAS No. | 100-02-7 |
|---|---|
| Summenformel | C6H5NO3 |
| Durchschnittliche Molmasse | 139,11 g/mol |
| Monoisotopische Masse | 139,02694302 g/mol |
| SMILES | O=[N+]([O-])c1ccc(O)cc1 |
| InChIKey | BTJIUGUIPKRLHP-UHFFFAOYSA-N |
| PubChem CID | 980 |
| ChEMBL | CHEMBL14130 |
| ChEBI | CHEBI:16836 |
| EC No. | 202-811-7 |
| DTXSID | DTXSID0021834 |
| Lokaler Name | 4-Nitrophenol |
Chemische & physikalische Eigenschaften
| XLogP | 1,9 |
|---|---|
| Polarare Oberfläche (TPSA) | 66,1 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 123 |
| Stoffklassen | Hazardous Air Pollutants (HAPs)Nitrogen Compounds -> NitrophenolsReactive agents - 2nd degreeDyeSemi-Volatile Organic Compound (SVOC) |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| Pestizide | Pesticide -> EPA IRIS |
| LogP (Verteilungskoeffizient) | log Kow = 1.911.95 |
| Geruch | Odorless |
| Geschmack | Sweetish, then burning tasteTASTE /THRESHOLD/ CONCENTRATION 43.4 MG/L. |
| Dichte | 1.48 at 68 °F (USCG, 1999) - Denser than waterwill sink1.479 g/cu cm at 20 °C1.5 g/cm³1.479 @ 20°C1,27 g/cm3 |
| Color/Form | Colorless to slightly yellow crystalsYELLOW TO BROWN SOLID |
| Löslichkeit | less than 0.1 mg/mL at 70 °F (NTP, 1992)Solubility in water, 269,000 mg/L at 90 °CFreely soluble in alcohol, chloroform, ethersoluble in solution of fixed alkali hydroxides and carbonatesVery soluble in ethanol, ether, and acetoneIn water, 32.8 g/L at 40 °Cethanol: soluble95%, clear, dark yellow (100 mg/mL)1.6 g/100 mL (25 ºC) |
| Flammpunkt | 377 °F (NTP, 1992)169 °C |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Schmelzpunkt | 112 °C |
| Siedepunkt | 279 °C(lit.) |
| Dampfdruck | 0.6 mm Hg ( 120 °C) |
| Brechungsindex | 1.5723 (estimate) |
| Lagerbedingungen | 2-8°C |
| pKa (Säurekonstante) | 7.15(at 25℃) |
| Aggregatzustand | Crystalline Powder, Crystals and/or Chunks |
| Farbe | Yellow to brown |
| Wichte | 1.479 |
| Geruch | Odorless |
| pH | 4.4 (5g/l, H2O, 24℃)(anhydrous substance) |
| Merck | 14,6620 |
| BRN | 1281877 |
| Henry-Konstante | 1.63 x 10-7 at 5 °C (average derived from six field experiments, Lüttke and Levsen, 1997) |
| Stabilität | Stable. Incompatible with strong oxidizing agents, strong bases, organics, combustible material, reducing agents. Combustible. |
| Hauptanwendungen | Display device, solar cells, nanoparticles, electrolytic capacitors, lithographic printing plate, leak detection method, falsification-proof security paper, correction fluid, detergent, fertilizer, identifying fresh and stale rice, diapers, detecting lactic acid bacteria, drug delivery, evaluating dental caries activity |
| Kosmetik-Inhaltsstoffe Funktionen | HAIR DYEING |
| InChI | 1S/C6H5NO3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H |
| InChIKey | BTJIUGUIPKRLHP-UHFFFAOYSA-N |
| SMILES | O=N(C1=CC=C(O)C=C1)=O |
| CAS Datenbank | 100-02-7(CAS DataBase Reference) |
| NIST chemische Informationen | Phenol, 4-nitro-(100-02-7) |
| EPA chemische Informationen | p-Nitrophenol (100-02-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302: Harmful if swallowed [Warning Acute toxicity, oral]P260, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P319, P321, P330, P362+P364, and P501 (click each P-code to see the statement)DangerH301 (77.6%): Toxic if swallowed [Danger Acute toxicity, oral]P260, P261, P264, P270, P271, P273, P280, P301+P316, P301+P317, P302+P352, P304+P340, P317, P319, P321, P330, P362+P364, P405, and P501 (click each P-code to see the statement) |
|---|---|
| Regulatorische Informationen | Chemical: Phenol, 4-nitro-Hazard Traits - DermatotoxicityEnvironmental toxOther Toxicological Hazard TraitsStatus: Active Update: 24-02-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/136764-Nitrophenol: Does not have an individual approval but may be used under an appropriate group standardThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| Weitere Sicherheitsinformationen | IMAP assessments - Phenol, 4-nitro-: Human health tier II assessment |
| DOT-Kennzeichnung | Poison |
| Brandgefahren | Special Hazards of Combustion Products: Toxic oxides of nitrogen and fumes of unburned material may form in fires.Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air. |
| Brandpotenzial | ... Will burn even in absence of air.AROMATIC NITROCOMPOUNDS ARE FLAMMABLE ... /AROMATIC NITROCMPD/ |
| Gesundheitsgefahren | Inhalation or ingestion causes headache, drowsiness, nausea, and blue color in lips, ears, and fingernails (cyanosis). Contact with eyes or skin causes irritationcan be absorbed through skin to give same symptoms as for inhalation. (USCG, 1999) |
| Gefahrenübersicht | 4-Nitrophenol is used to manufacture drugs, fungicides, insecticides, and dyes and to darken leather. Acute (short-term) inhalation or ingestion of 4-nitrophenol in humans causes headaches, drowsiness, nausea, and cyanosis (blue color in lips, ears, and fingernails). Contact with eyes causes irritation in humans. No information is available on the chronic (long-term) effects of 4-nitrophenol in humans or animals from inhalation or oral exposure. No information is available on the reproductive, developmental, or carcinogenic effects of 4-nitrophenol in humans. EPA has not classified 4-nitrophenol for potential carcinogenicity.Methemoglobinemia has been reported. [HSDB] 4-Nitrophenol is more toxic than 2-nitrophenol in animals. Rats exposed to 2-nitrophenol at 112 mg/m3 for 2 weeks develop methemoglobinemia. No effect after dust exposures of 30 mg/m3 for 3-6 hours/day, 5 days a week for 4 weeks[ATSDR ToxProfiles] A skin, eye, and respiratory tract irritantMay cause yellow stains on the skinCan induce methemoglobinemiaMay cause skin sensitization[ICSC]The major hazards encountered in the use and handling of 4-nitrophenol stem from its toxicologic properties. Toxic by all routes (ie, inhalation, ingestion, dermal absorption), exposure to this odorless, colorless to yellow, crystalline substance, may occur from its use as a fungicide for leather products, or as a chemical intermediate in the syntheses of methyl and ethyl parathion. Effects from exposure may include burns to the skin and eyes, headache, dizziness, shock, unconsciousness, and death from cardiac or pulmonary failure. Contact with 4-nitrophenol should be protected against by wearing butyl rubber gloves, boots, chemical protective clothing which is specifically recommended by the shipper or producer, and a dust mask, organic vapor canister respirator, or in emergency situations, a self-contained breathing apparatus. If contact does occur, immediately flush affected skin or eyes with running water for at least 15 minutes, and remove and isolate contaminated clothing at the site. While 4-nitrophenol does not ignite easily, it can burn, emitting toxic oxides of nitrogen. Also, containers may explode in the heat of a fire. For small fires involving 4-nitrophenol, extinguish with dry chemical, CO2, Halon, water spray, or standard foam, and for large fires, use water spray, fog, or standard foam. Runoff from fire control water may give off poisonous gases or cause pollution, and should be controlled by diking, as necessary. 4-Nitrophenol should be stored in a cool, ventilated, fireproofed area, away from oxidizing agents, oxidiazable materials, and sources of ignition and physical damage. Small spills of 4-nitrophenol may be taken up (if liquid, with sand or other noncombustible absorbent) and placed into containers for later disposal. Large spills should be contained in pits, or other holding areas that are sealed with an impermeable flexible membrane liner. Solids should be covered with a plastic sheet. Liquids should be neutralized with slaked lime, crushed limestone, or sodium bicarbonate, and diked, if necessary, to prevent runoff from entering water sources or sewers. Spills of 4-nitrophenol in water may need to be trapped at the bottom with sand bag barriers, activated charcoal applied, and the trapped material removed with suction hoses, mechanical dredges, or lifts. Prior to implementing permanent land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance. Also, 4-nitrophenol is a potential candidate for rotary kiln or fluidized bed forms of incineration. |
| Reaktive Gruppe | Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic |
| EG-Einstufung | Symbol: XnR: 20/21/22-33S: (2)-28 |
| UN-Einstufung | UN Hazard Class: 6.1UN Pack Group: III |
| Special Reports | USEPA/Office of Pesticide ProgramsReregistration Eligibility Decision Document - Paranitrophenol, EPA 738-R-97-016 (January 1998). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of February 15, 2012: http://www.epa.gov/pesticides/reregistration/status.htm]Ambient Water Quality Criteria Doc: Nitrophenol (1980) EPA 440/5-80-063Dean BJMutat Res 47: 75-97 (1978). A review with 90 references on the mutagenicity, biotransformations, & toxicity of benzene, toluene, xylene, & phenols including o-nitrophenol.Bablch H, Borenfreund EEnviron Res 42 (1): 229-37 (1987). BF-2 cells, an established cell line derived from bluegill sunfish, (Lepomis macrochirus), were exposed to 18 organic toxicants, with cytotoxicity being assayed by the neutral red technique.For more Special Reports (Complete) data for 4-NITROPHENOL (7 total), please visit the HSDB record page. |
| RCRA-Anforderungen | U170As stipulated in 40 CFR 261.33, when p-nitrophenol, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5). |
| Brandbekämpfung | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:Use water spray, powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest. Refer for medical attention.Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Rest. Refer for medical attention . |
| Erste Hilfe | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. |
| Sichere Lagerung | Separated from combustible substances, reducing agents and food and feedstuffs. Well closed. |
| Brandbekämpfungsverfahren | Use water spray, dry chemical, foam, or carbon dioxide. Use water spray to keep fire-exposed containers cool. Approach fire from upwind to avoid hazardous vapors and toxic decomposition products. Fight fire from protected location or maximum possible distance.If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use foam, dry chemical, or carbon dioxide. Keep run-off water out of sewers and water sources. /Nitrophenols/ |
| Lagerbedingungen | ... KEEP ALL FLAMMABLES AWAY FROM AREA WHERE OXIDIZING AGENTS ARE STORED. ... AREA ... KEPT COOL & VENTILATED, & SHOULD BE FIREPROOFED.Store in a cool, dry, well-ventilated location. Separate from alkalies and oxidizing materials. |
| Reinigungsverfahren | Spill or leak procedures: Shovel into suitable dry container. |
| Freisetung ohne Brand | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| Entsorgungsverfahren | SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U170, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.[Potential candidate for rotary kiln incineration, with a temperature range of 820 to 1,600 °C and a residence time of hours. Also a potential candidate for fluidized bed incineration, with a temperature range of 450 to 980 °C and a residence time for liquids and gasesseconds: solidslonger.Nitrophenol is a waste chemical stream constituent which may be subjected to ultimate disposal by controlled incineration. /SRP: Incineration must be controlled./ Care must be taken to maintain complete combustion at all times. Incineration of large quantities may require scrubbers to control the emission of NOx. /Nitrophenol cmpd/For more Disposal Methods (Complete) data for 4-NITROPHENOL (10 total), please visit the HSDB record page. |
| Verschüttetes entsorgen | Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. |
| Preventive Measures | ... Clean work clothes should be supplied dailyshowers should be taken prior to changing to street clothes. ... Appropriate type respirators with organic vapor canisters should be provided in areas of concn of dust or vapors. /Nitrophenols/SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.For more Preventive Measures (Complete) data for 4-NITROPHENOL (6 total), please visit the HSDB record page. |
| Isolation and Evacuation | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| Körperbelastung | Health and Nutrition Examination Survey II: 4-Nitrophenol was identified, not quantified, in the urine of 168 of 6,990 persons that had been exposed to methyl and ethyl parathion(1). Parathion sprayers had detectable levels of 4-nitrophenol of 1.587-8.571 ug/mL in urine(2). 4-Nitrophenol was detected in 57% of 15,904 urine samples collected from residents in seven states in the US at a mean and median concentration of 75 and 31 ug/L, respectively(3)4-nitrophenol is used as a biomarker of methyl parathion exposure(3). |
| Treatment | Methemoglobinemia can be treated with supplemental oxygen and methylene blue 1% solution at 1-2mg/kg administered intravenously slowly over five minutes followed by an IV flush with normal saline. Methylene blue restores the iron in hemoglobin to its normal (reduced) oxygen-carrying state. (L1613) |
| Gesundheitliche Auswirkungen | Nitrophenols may cause methemoglobinemia. This is a disorder in which there is an abnormally high level of methemoglobin in the blood, resulting in a decrease in the amount of oxygen that can be carried to the tissues and organs. (L1661, L1613) |
| Ökotoxizitätswerte | Toxicity threshold (pollutant concn causing the onset of cell multiplication inhibition) Scenedesmus quardricauda (alga) 7,400 ug/L/8 daysToxicity threshold (pollutant concn causing the onset of cell multiplication inhibition) Microcystis aeruginosa (alga) 6,000 ug/L/8 days42% Mortality Carassius auratus (goldfish) 8000 ug/L/8 hrLethal threshold (pollutant concn causing the onset of cell multiplication inhibition) Mya arenaria (clam, soft shell) 29,400 ug/L/96 hrFor more Ecotoxicity Values (Complete) data for 4-NITROPHENOL (49 total), please visit the HSDB record page. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), a median literature Koc value of 234 (log Koc = 2.37) reported for 4-nitrophenol(2) indicates that 4-nitrophenol is expected to have moderate mobility in soil(SRC). However, measured Koc values range from 16(3) to over 500(4) suggesting a range of very high mobility to low mobility(SRC). The pKa of 4-nitrophenol is 7.15(5), indicating that this compound will exist partially in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(6). The available experimental data suggests 4-nitrophenol may be more mobile in anionic form(SRC). Volatilization of 4-nitrophenol from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 1.28X10-8 atm-cu m/mole(7). 4-Nitrophenol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 9.79X10-5 mm Hg at 20 °C(8). The biodegradation half-life of 4-nitrophenol in an acidic soil was reported as 2.5 days and the biodegradation half-life in a basic soil was reported as 10.2 days(9). However, a large number of biodegradation studies have shown that 4-nitrophenol can degrade over a wide range from very slow to fastin general, 4-nitrophenol degrades much faster in acclimated media(10).AQUATIC FATE: Based on a classification scheme(1), a median literature Koc value of 234(2) indicates that 4-nitrophenol may undergo some adsorption to suspended solids and sediment in water(SRC). Measured Koc values range from 16(3) to over 500(4) suggesting a range of adsorption potential with sediment(SRC). The pKa of 4-nitropehnol is 7.15(5), indicating that this compound will exist partially in anion form in the environment and anions generally do not adsorb more strongly than their neutral counterparts(6). Volatilization from water surfaces is not expected(7) based upon the Henry's Law constant of 1.28X10-8 atm-cu m/mole at 20 °C(8). According to a classification scheme(9), BCF values in the range of 2.5(10) to 79(11) in fish suggest bioconcentration in aquatic organisms will be low to moderate. 4-Nitrophenol is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(7). When 4-nitrophenol in water was exposed to sunlight, the half-life was 5.7, 6.7, and 13.7 days at pH 5, 7, and 9, respectively(12). The biodegradation half-life of 4-nitrophenol was reported as 18 hours and 6.8 days in aerobic and anaerobic waters, respectively(13). However, a large number of biodegradation studies have shown that 4-nitrophenol can degrade over a wide range from very slow to fastin general, 4-nitrophenol degrades much faster in acclimated media(14).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 4-nitrophenol, which has a vapor pressure of 9.79X10-5 mm Hg at 20 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. An urban monitoring study in Rome Italy found the concentration to be higher in the particulate-phase compared to the vapor-phase(3). Vapor-phase 4-nitrophenol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 3.7 days(SRC), calculated from its rate constant of 4.3X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(4). Particulate-phase 4-nitrophenol may be removed from the air by wet and dry deposition(SRC). Vapor-phase 4-nitrophenol is also removed from the ambient atmosphere through dissolution into cloud water with subsequent precipitation(5). 4-Nitrophenol absorbs UV light strongly above 290 nm(6) suggesting the compound is susceptible to direct photolysis in sunlight(SRC). 4-Nitrophenol adsorbed to silica gel was 39% mineralized when exposed to light greater than 290 nm over a 17 hour period(7). |
| Lebensmitteluntersuchungswerte | Lettuce sprayed with parathion (0.5 lb/acre) contained 0.061 ppm 4-nitrophenol at harvest on the trimmed head(1). |
| Unerwünschte Wirkungen | Methemoglobinemia - The presence of increased methemoglobin in the bloodthe compound is classified as secondary toxic effect |
| Expositionspfade | The substance can be absorbed into the body by inhalation, through the skin and by ingestion.Oral (L1661)inhalation (L1661)dermal (L1661) |
| Toxizitätsübersicht | The nitrite in nitrophenols causes the autocatalytic oxidation of oxyhemoglobin to hydrogen peroxide and methemoglobin. This elevation of methemoglobin levels is a condition known as methemoglobinemia, and is characterized by tissue hypoxia, as methemoglobin cannot bind oxygen. (A2450, L1613) |
| Ökotoxizitätsauszüge | /AQUATIC SPECIES/ 4-Nitrophenol concentrations > or = 10 mg/L were chronically toxic to Daphnia magna under both static renewal and flow-through conditions. Although growth and reproduction of the daphnids were both substantially better in the flow-through test, the 4-nitrophenol concentration that caused significant impacts on the populations were the same in both systems./AQUATIC SPECIES/ Flow-through, acute (96 hr) and early life stage (28 days after hatch) toxicity tests /SRP: on C variegatus (sheepshead minnows)/ revealed that max acceptable toxicant concentration (MATC) for 4-nitrophenol was >10 but <16 mg/L, with an application factor of 0.31-0.50./AQUATIC SPECIES/ The process of wet oxidation breaks down organic substances in aqueous solution at elevated temperature and pressures. Experimental wet oxidations were carried out on pure solutions of phenol, 2-chlorophenol and 4-nitrophenol. After 1 hr wet oxidation, final concentrations of these compounds averaged 3% of their concentrations in the starting solutions. The toxicities of the starting compounds and the residual toxicity of the end product solutions were measured with 48 hr acute toxicity tests using Daphnia magna. The solutions of end products were all less toxic than the starting solutions by factors of 10-120. The end product solutions were more toxic than would have been predicted from the known concentration of initial compound remaining in the solution of end products./AQUATIC SPECIES/ The relative toxic response to 27 selected phenols in 96 hr acute flow-through Pimephales promelas (fathead minnow) and 48-60 hr chronic static Tetrahymena pyriformis (ciliate protozoan) test systems were evaluated. Log Kow dependent linear regression analyses revealed that the data from each test system consisted of 2 linear equations. The less toxic chemicals form a relation which models polar CNS depressionthese chemicals are slightly more active than the baseline toxicity of nonionic chemicals. The more toxic chemicals form a relation which models upcoupling of oxidative phosphorylation. Regression analysis of fathead minnow toxicity (log median lethal concn (mol/L)) vs Tetrahymena pyriformis toxicity (log of the 48-60 hr 50% inhibitory concn (BR), mmol/L) showed good correlation between the 2 systems. An exception is 4-nitrophenol which is more active in the Tetrahymena system than in the fathead minnow /system/.For more Ecotoxicity Excerpts (Complete) data for 4-NITROPHENOL (13 total), please visit the HSDB record page. |
| Signs and Symptoms | Blue lips, fingernails and skin. Cough. Burning sensation. Confusion. Convulsions. Dizziness. Headache. Nausea. Sore throat. Unconsciousness. Weakness.MAY BE ABSORBED! Redness. Further see Inhalation.Redness. Pain.Abdominal pain. Sore throat. Vomiting. See Inhalation.Symptoms of methemoglobinemia include shortness of breath, cyanosis, mental status changes, headache, fatigue, exercise intolerance, dizziness and loss of consciousness. Severe methemoglobinemia may cause dysrhythmias, seizures, coma and death. (L1613) |
| Ongoing Test Status | The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=100-02-7] |
| TSCA-Anforderungen | Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. p-Nitrophenol is included on this list. Effective date: 4/13/89Sunset date: 6/30/98. |
| FIFRA-Anforderungen | Based on the reviews of the generic data for the active ingredient paranitrophenol, the Agency has some concerns about paranitrophenol relating to the potential for handler dermal and inhalation exposure associated with the registered uses of paranitrophenol (i.e., leather and cork treatment applied by military contractors to products used by military workers). Lacking adequate exposure and toxicity data, the Agency is unable to conduct a quantitative risk assessment. In order to assess the risk ... /addtitional/ data would be required to support the continued registration of paranitrophenol ... The Agency contacted the sole registrant of paranitrophenol, the United States Department of the Army, regarding the data necessary to support the continued registration of paranitrophenol. Subsequently, the Agency received a request to cancel the registration of the sole product containing paranitrophenol from the Department of the Army to take effect on May 30, 2002.As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer saftey standards, such as those described in the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List C, and with List C containing pesticides of greater concern than those on List D. 4-Nitrophenol is found on List B. Case No: 2465Pesticide type: fungicideCase Status: RED Approved 9/97OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document .Active ingredient (AI): 4-nitrophenolData Call-in (DCI) Date(s): 2/12/91AI Status: OPP has completed a Reregistration Eligibility Decision (RED) for the case/AI. |
| Luftstandards | Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. 4-Nitrophenol is included on this list. |
| CERCLA-Meldepflichtmengen | Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b). |
| Clean Water Act Anforderungen | 4-Nitrophenol is designated as a hazardous substance under section 311(b)(2)(A) of the Federal Water Pollution Control Act and further regulated by the Clean Water Act Amendments of 1977 and 1978. These regulations apply to discharges of this substance. This designation includes any isomers and hydrates, as well as any solutions and mixtures containing this substance.Toxic pollutant designated pursuant to section 307(a)(1) of the Federal Water Pollution Control Act and is subject to effluent limitations. /Nitrophenols (including 2,4-dinitrophenol, dinitrocresol)/ |
| Bundesrichtlinien für Trinkwasser | EPA 60 ug/l |
| F | 8 |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 1663 (NITROPHENOLS (o-, m-, p-)) |
| Zollcode | 29089000 |
| RTECS-Nr. | SM2275000 |
| R-Sätze (R) | 20/21/22-33-39/23/24/25-23/24/25-11 |
| Toxizität | LD50 orally in mice, rats: 467, 616 mg/kg, K.C. Back et al., Reclassification of Materials Listed as Transportation Health Hazards (TSA-20-72-3PB214-270, 1972) |
| Gefahrensymbole | Xn,T,F |
| Sicherheitshinweise (S) | 28-28A-45-36/37-16-7 |
| Gefahrenklasse | 6.1Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralSTOT RE 2 Oral |
| Verpackungsgruppe | III |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Gefahrstoffdaten | 100-02-7(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 541 °F |
Anwendungen & Verwendung
Beschreibung
4-Nitrophenol (also called p-nitrophenol or 4-hydroxynitrobenzene) is a phenolic compound that has a nitro group at the opposite position of hydroxyl group on the benzene ring. 4-Nitrophenol shows two polymorphs in the crystalline state. The alpha form is colorless pillars, unstable at room temperature, and stable toward sunlight. The beta form is yellow pillars, stable at room temperature, and gradually turns red upon irradiation of sunlight. Usually 4-nitrophenol exists as a mixture of these two forms. Generally, 4-nitrophenol is used in manufacturing of drugs (e.g., acetaminophen), fungicides, methyl and ethyl parathion insecticides, and dyes, and to darken leather.
Verwenden
4-Nitrophenol is used in dyestuff and pesticide synthesis, as a fungicide, bactericide, and wood preservative, as a chemical indicator, and as a substrate for experiments on cytochrome P450 2E1.4-Nitrophenol is used as a precursor to prepare phenetidine, acetophenetidne and pH indicator. Its carboxylate ester derivatives are involved as an active component for the construction of amide moieties in peptide synthesis. It is used as an intermediate in the synthesis of paracetamol and N-acetyl-p-aminophenol dyestuffs.
Herstellung & Synthese
synthetische
4-Nitrophenol was synthesized from p-nitrochlorobenzene by hydrolysis and acidification. Add 2320-2370L of sodium hydroxide solution with a concentration of 137-140g/L to the hydrolysis pot, and then add 600kg of molten p-nitrochlorobenzene. Heat to 152℃, pressure in the pot is 0.4MPa, then stop heating, the hydrolysis reaction exotherm makes the temperature and pressure rise naturally to 165℃, about 0.6MPa. keep 3h and take sample to check the end point of the reaction, after the reaction is finished, the hydrolysate is cooled to 120℃. Add 600L water and 50L concentrated sulfuric acid to the crystallization pot, press into the above hydrolysis and cool to about 50℃, add concentrated sulfuric acid to make the Congo red test paper purple, continue to cool to 30℃, filter, centrifuge to shake off the water, get more than 90% of 4-nitrophenol about 500kg, 92% yield.