HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
2,4-Dinitrophenol
2,4-DNP · 2,4-Dinitrofenol · 2,4-dinitrophenol, reagent grade · Aldifen · Dinitrophenols · 2,4-DINITROPHENOL, 1X1ML, MEOH, 5000UG/M L · X 32 · EK 102
Identifikatoren & physikalische Daten
| CAS No. | 51-28-5 |
|---|---|
| Summenformel | C6H4N2O5 |
| Durchschnittliche Molmasse | 184,11 g/mol |
| Monoisotopische Masse | 184,01202123 g/mol |
| SMILES | O=[N+]([O-])c1ccc(O)c([N+](=O)[O-])c1 |
| InChIKey | UFBJCMHMOXMLKC-UHFFFAOYSA-N |
| PubChem CID | 1493 |
| ChEMBL | CHEMBL273386 |
| ChEBI | CHEBI:42017 |
| EC No. | 200-087-7 |
| DTXSID | DTXSID0020523 |
| Lokaler Name | 2,4-Dinitrophenol |
Chemische & physikalische Eigenschaften
| XLogP | 1,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 112 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 5 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 13 |
| Formalladung | 0 |
| Komplexität | 220 |
| pH | pH range: 2.6 Colorless, 4.4 Yellow |
| LogP (Verteilungskoeffizient) | 1.67log Kow = 1.671.67 (estimated) |
| Geruch | SWEET, MUSTY ODOR |
| Geschmack | BITTER TASTE |
| Dichte | 1.68 at 68 °F (USCG, 1999) - Denser than waterwill sink1.683 g/cu cm at 24 °CRelative density (water = 1): 1.681.683 @ 24°C1,683 g/cm3 |
| Color/Form | Pale yellow platelets or leaflets from waterYellowish to yellow orthorhombic crystals |
| Löslichkeit | less than 1 mg/mL at 67.1 °F (NTP, 1992)2790Soluble in ethanol, ethyl ether, benzene, methanolSolubility at 15 °C (g/100 g solution): ethyl acetate 15.55acetone 35.90chloroform 5.39pyridine 20.08carbon tetrachloride 0.423toluene 6.36Soluble in aqueous alkaline solutionsIn water, 5,600 mg/L at 18 °C43,000 mg/L at 100 °CSolubility Sparingly soluble in watersoluble in ethanol, benzene0.6 g/100 mL (18 ºC) |
| Siedepunkt | Sublimes (when carefully heated) (NTP, 1992)318.03°C (rough estimate) |
| Decomposition | When heated to decomposition it emits toxic fumes of /nitroxides/.May explosively decompose on shock, friction, or concussion. |
| Schmelzpunkt | 234 to 237 °F (NTP, 1992)115.5114.8 °C112 °C108-112 °C (lit.) |
| Dampfdichte | 6.35 (NTP, 1992) - Heavier than airwill sink (Relative to Air)6.35 (Air = 1)Relative vapor density (air = 1): 6.366.35 (vs air) |
| Dampfdruck | 0.00039 [mmHg]3.9X10-4 mm Hg at 20 °C39(x 10-5 mmHg) at 20 °C (Schwarzenbach et al., 1988) |
| Brechungsindex | 1.4738 (estimate) |
| Flammpunkt | 11 °C |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | crystals |
| pKa (Säurekonstante) | 3.96(at 15℃) |
| Farbe | Light yellow |
| Geruch | Sweet, musty |
| Merck | 14,3280 |
| BRN | 1246142 |
| Henry-Konstante | 5.70 x 10-8(atmm3/mol) at 5 °C (average derived from six field experiments, Lüttke and Levsen, 1997) |
| Stabilität | Stable. Combustible. |
| Hauptanwendungen | Display device, recording materials, inks, paints, method for preserving food, method for gene expression profiling, treatment of parasitic diseases, neurological diseases, epilepsy, cancer, keratin materials, neoplasms, infectious diseases, neutropenia, detecting chromosome aberrations, bacteria in gastrointestinal track |
| InChI | 1S/C6H4N2O5/c9-6-2-1-4(7(10)11)3-5(6)8(12)13/h1-3,9H |
| InChIKey | UFBJCMHMOXMLKC-UHFFFAOYSA-N |
| SMILES | Oc1ccc(cc1[N+]([O-])=O)[N+]([O-])=O |
| CAS Datenbank | 51-28-5(CAS DataBase Reference) |
| NIST chemische Informationen | Phenol, 2,4-dinitro-(51-28-5) |
| EPA chemische Informationen | 2,4-Dinitrophenol (51-28-5) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH300: Fatal if swallowed [Danger Acute toxicity, oral]H311: Toxic in contact with skin [Danger Acute toxicity, dermal]H331: Toxic if inhaled [Danger Acute toxicity, inhalation]H372: Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]P260, P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P319, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement) |
|---|---|
| Regulatorische Informationen | Chemical: Phenol, 2,4-dinitro-Hazard Traits - Hazard Trait UndefinedAuthoritative List - CA TACsCWA 303(c)Report - if used as a fragrance or flavor ingredientStatus: Active Update: 09-03-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/10875Phenol, 2,4-dinitro- (wetted with not less than 15% water by mass): HSNO Approval: HSR001273 Approved with controlsThe 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.) |
| DOT-Kennzeichnung | Flammable Solid Poison |
| Brandgefahren | Combustible. May explode if subjected to heat or flame. POISONOUS GAS IS PRODUCED WHEN HEATED. Vapors are toxic. Can detonate or explode when heated under confinement. (USCG, 1999)· Combustible material: may burn but does not ignite readily.· When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards.· Those substances designated with a (P) may polymerize explosively when heated or involved in a fire.· Corrosives in contact with metals may evolve flammable hydrogen gas.· Containers may explode when heated.· Runoff may pollute waterways.· Substance may be transported in a molten form.· Flammable/combustible material.· May be ignited by heat, sparks or flames.· DRIED OUT material may explode if exposed to heat, flame, friction or shocktreat as an explosive (GUIDE 112).· Keep material wet with water or treat as an explosive (GUIDE 112).· Runoff to sewer may create fire or explosion hazard.Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Risk of fire and explosion. |
| Brandpotenzial | The flammability of the solution depends on the nature of the solvent. Dintrophenol is combustible though it may require some effort to ignite. /Dinitrophenol solutions/The wet material can burn though it may require some effort to ignite. /Dinitrophenol, wetted with at least 15% water/ |
| Gesundheitsgefahren | DUST: POISONOUS IF INHALED OR IF SKIN IS EXPOSED. SOLID: POISONOUS IF SWALLOWED. (USCG, 1999)· TOXIC and/or CORROSIVEinhalation, ingestion or skin contact with material may cause severe injury or death.· Methyl bromoacetate (UN2643) is an eye irritant/lachrymator (causes flow of tears).· Contact with molten substance may cause severe burns to skin and eyes.· Avoid any skin contact.· Fire may produce irritating, corrosive and/or toxic gases.· Runoff from fire control or dilution water may be corrosive and/or toxic and cause environmental contamination.· Some are toxic and may be fatal if inhaled, ingested or absorbed through skin. Specifically, Dinitrophenol, wetted (UN1320)Dinitrophenolates, wetted (UN1321), Sodium dinitro-o-cresolate, wetted (UN1348)and Barium azide, wetted (UN1571) are known to be toxic.· Contact may cause burns to skin and eyes.· Runoff from fire control or dilution water may cause environmental contamination. |
| Gefahrenübersicht | 2,4-Dinitrophenol is used in the manufacture of dyes, wood preservatives, and as a pesticide. The acute (short-term) effects of 2,4-dinitrophenol in humans through oral exposure are nausea, vomiting, sweating, dizziness, headaches, and loss of weight. Chronic (long-term) oral exposure to 2,4-dinitrophenol in humans has resulted in the formation of cataracts and skin lesions, weight loss, and has caused effects on the bone marrow, central nervous system (CNS), and cardiovascular system. Limited or no information is available on the developmental, reproductive, or carcinogenic effects of 2,4-dinitrophenol in humans. EPA has not classified 2,4-dinitrophenol for carcinogenicity.In the 1930s, it was used to treat obesity. Reported adverse effects included agranulocytosis, neuritis, and heart damage. Poisoning by ingestion causes uncoupling of oxidative phosphorylation with high fever, sweating, tachycardia, abdominal pain, anxiety, rapid breathing that may end in convulsions and death. Poisoning has also caused toxic hepatitis, renal failure, and cataract formation. [HSDB] May cause first degree burns after short exposure and second degree burns after longer contactMay cause cataracts after chronic exposure[CHRIS] There is a case report of dinitrophenol causing cholestatic jaundice. [Zimmerman, p. 351] See Dinitrophenol.The major hazards encountered in the use and handling of 2,4-dinitrophenol stem from its toxicologic properties. Toxic by all routes (ie, inhalation, ingestion, dermal absorption), exposure to this sweet-smelling, yellowish, crystalline substance, may occur from its use as a pesticide on wood products, and as a chemical intermediate in the production of dyes. Effects from exposure may include burns to the skin and eyes, headache, fatigue, nausea, anxiety, loss of consciousness, and death due to cardiac or pulmonary collapse. Exposure should be minimized by the use of exhaust ventilation. In addition, it is recommended that exposure be protected against by wearing butyl rubber gloves, chemical protective clothing which is specifically recommended by the shipper or producer, and, 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. 2,4-Dinitrophenol may be ignited by heat, sparks, or flames. Poisonous oxides of nitrogen are produced in a fire. Further, its vapor may explode in confined spaces, or, if the substance becomes dry, it may explode upon contact. For small fires involving 2,4-dinitrophenol, extinguish with dry chemical, CO2, Halon, water spray, or standard foam, and for large fires, use water spray, fog, or standard foam. Fight fires from a maximum distance, using an unmanned hose holder to cool containers well after the fire is out. Runoff from fire control water should be diked to prevent it from entering water sources or sewers. Stored 2,4-dinitrophenol should be kept wet with water, or treated as an explosive. Storage should be in cool, ventilated areas, away from sources of ignition, oxidizing agents, combustible materials, and heavy metals and their compounds. 2,4-Dinitrophenol which is dry, or which is wetted with not less than 15% water by weight is subject to additional restrict |
| DOT-Nummer und Handbuch | 1599 1531320 113 |
| Reaktive Gruppe | Nitro, Nitroso, Nitrate, and Nitrite Compounds, OrganicPhenols and Cresols |
| EG-Einstufung | Symbol: T, NR: 23/24/25-33-50S: (1/2)-28-37-45-61 |
| UN-Einstufung | UN Hazard Class: 4.1UN Subsidiary Risks: 6.1UN Pack Group: I |
| Special Reports | USEPAHealth and Environmental Profiles for Dinitrophenols 39p (1988) EPA/600/X-84/153. Health and Environmental Effects Profile for 2,4-Dinitrophenol.U.S. Dept Health & Human Services/Agency for Toxic Substances Disease RegistryToxicological Profile for Dinitrophenols (1995) NTIS# PB/95/264339 |
| RCRA-Anforderungen | P048As stipulated in 40 CFR 261.33, when 2,4-dinitrophenol, 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 container or inner liner used to hold this waste or 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(e)). |
| Brandbekämpfung | Excerpt from ERG Guide 113 [Flammable Materials (Wet / Desensitized Explosive)]:CARGO FIRE: DO NOT fight fire when fire reaches cargo! Cargo may EXPLODE! Stop all traffic and clear the area for at least 1600 meters (1 mile) in all directions and let burn. Do not move cargo or vehicle if cargo has been exposed to heat.TIRE OR VEHICLE FIRE: Use plenty of water - FLOOD it! If water is not available, use CO2, dry chemical or dirt. If possible, and WITHOUT RISK, use unmanned master stream devices or monitor nozzles from maximum distance to prevent fire from spreading to cargo area. Pay special attention to tire fires as re-ignition may occur. Stand by, at a safe distance, with extinguisher ready for possible re-ignition. (ERG, 2024)Use water in large amounts. In case of fire: keep drums, etc., cool by spraying with water. Combat fire from a sheltered position. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest.Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer immediately for medical attention .First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rest. Refer immediately for medical attention. |
| Freisetungsmaßnahmen | · CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.· Keep unauthorized personnel away.· Stay upwind, uphill and/or upstream.· Ventilate closed spaces before entering, but only if properly trained and equipped.· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.· Do not touch damaged containers or spilled material unless wearing appropriate protective clothing.· Stop leak if you can do it without risk.· Prevent entry into waterways, sewers, basements or confined areas.· Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers.· DO NOT GET WATER INSIDE CONTAINERS.· All equipment used when handling the product must be grounded.· Do not touch or walk through spilled material.Small Spill· Flush area with large amounts of water.Large Spill· Wet down with water and dike for later disposal.· KEEP "WETTED" PRODUCT WET BY SLOWLY ADDING FLOODING QUANTITIES OF WATER. |
| 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.SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas.INHALATION: IMMEDIATELY leave the contaminated areatake deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be usedif not available, use a level of protection greater than or equal to that advised under Protective Clothing.INGESTION: DO NOT INDUCE VOMITING. Phenols are very toxic poisons AND corrosive and irritating, so that inducing vomiting may make medical problems worse. IMMEDIATELY call a hospital or poison control center and locate activated charcoal, egg whites, or milk in case the medical advisor recommends administering one of them. If advice from a physician is not readily available and the victim is conscious and not convulsing, give the victim a glass of activated charcoal slurry in water or, if this is not available, a glass of milk, or beaten egg whites and IMMEDIATELY transport victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, assure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)General First Aid:· Call 911 or emergency medical service.· Ensure that medical personnel are aware of the material(s) involved, take precautions to protect themselves and avoid contamination.· Move victim to fresh air if it can be done safely.· Administer oxygen if breathing is difficult.· If victim is not breathing:-- DO NOT perform mouth-to-mouth resuscitationthe victim may have ingested or inhaled the substance.-- If equipped and pulse detected, wash face and mouth, then give artificial respiration using a proper respiratory medical device (bag-valve mask, pocket mask equipped with a one-way valve or other device).-- If no pulse detected or no respiratory medical device available, provide continuous compressions. Conduct a pulse check every two minutes or monitor for any signs of spontaneous respirations.· Remove and isolate contaminated clothing and shoes.· For minor skin contact, avoid spreading material on unaffected skin.· In case of contact with substance, remove immediately by flushing skin or eyes with running water for at least 20 minutes.· For severe burns, immediate medical attention is required.· Effects of exposure (inhalation, ingestion, or skin contact) to substance may be delayed.· Keep victim calm and warm.· Keep victim under observation.· For further assistance, contact your local Poison Control Center.· Note: Basic Life Support (BLS) and Advanced Life Support (ALS) should be done by trained professionals.Specific First Aid:· For corrosives, in case of contact, immediately flush skin or eyes with running water for at least 30 minutes. Additional flushing may be required.In Canada, an Emergency Response Assistance Plan (ERAP) may be required for this product. Please consult the shipping paper and/or the "ERAP" section. |
| Sichere Lagerung | Fireproof. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing. Cool. Separated from combustible substances, reducing agents and food and feedstuffs. |
| Firefighting Hazards | The primary hazard is from blast effect where the entire load can explode instantaneously and not from flying projectiles and fragments. /Dinitrophenol, dry/ |
| Expositionsschutz und Persönliche Schutzausrüstung | · Wear positive pressure self-contained breathing apparatus (SCBA).· Wear chemical protective clothing that is specifically recommended by the manufacturer when there is NO RISK OF FIRE.· Structural firefighters' protective clothing provides thermal protection but only limited chemical protection. |
| Brandbekämpfungsverfahren | If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide. /Dinitrophenol solutions/If material on fire or involved in fire: Dangerously explosive. Do not fight fires in a cargo of explosives. Evacuate area and let burn. /Dinitrophenol, dry or wetted with less than 15% water by weight)If material on fire or involved in fire: Dangerously explosive. Flood with water. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. /Dinitrophenol, wetted with at least 15% water/Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. |
| Lagerbedingungen | /Dinitrophenol/ ... should be stored in a cool ventilated place away from area of acute fire hazard and away from powerful oxidizing agents. /Dinitrophenol/ |
| Reinigungsverfahren | Evacuate persons not wearing protective equipment from area of spill or leak until clean-up is complete. Remove all ignition sources. Wet spilled material with water. Collect powdered material in the most convenient and safe manner and deposit in sealed containers. Ventilate area after clean-up is complete. It may be necessary to contain and dispose of this chemical as a hazardous waste. Keep dinitrophenol out of a confined space, such as a sewer, because of the possibility of an explosion, unless the sewer is designed to prevent the build-up of explosive concentrations. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental Protection of your regional office of the federal EPA for specific recommendations.Environmental considerations: Land spill: Dig a pit, pond, lagoon, or holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be contained with a flexible impermeable membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash or cement powder. /Dinitrophenol solutions/Environmental considerations: Water spill: use natural barriers or oil spill control booms to limit spill travel. use surface active agent (e.g., detergent, soaps, alcohols), if approved by EPA. Inject "universal" gelling agent to solidify encircled spill and increase effectiveness of booms. If dissolved in region of 10 ppm or greater concentration, apply activated carbon at ten times the spilled amount. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates. /Dinitrophenol solutions/Environmental considerations - land spill: dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water. /Dinitrophenol, wetted with at least 15% water/Environmental considerations - water spill: Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. If dissolved in region of 10 ppm or greater concentration, apply activated carbon at ten times the spilled amount. Remove trapped material with suction hoses. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates. /Dinitrophenol, wetted with at least 15% water/ |
| Freisetung ohne Brand | Excerpt from ERG Guide 113 [Flammable Materials (Wet / Desensitized Explosive)]:ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. All equipment used when handling the product must be grounded. Do not touch or walk through spilled material.SMALL SPILL: Flush area with large amounts of water.LARGE SPILL: Wet down with water and dike for later disposal. KEEP "WETTED" PRODUCT WET BY SLOWLY ADDING FLOODING QUANTITIES OF WATER. (ERG, 2024) |
| Entsorgungsverfahren | Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number P048, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.Dinitrophenol: Incinerate (1800 °F, 2.0 sec minimum) with adequate scrubbing equipment for the removal of NOx. Dinitrophenol ... /is a/ waste chemical stream constituent which may be subjected to ultimate disposal by controlled incineration. /Dinitrophenol/A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids.Chemical Treatability of 2,4-DinitrophenolConcentration Process: Biological Treatment. Chemical Classification: PhenolScale of Study: Respirometer StudyType of Wastewater Used: Synthetic WastewaterResults of Study: Max oxygen uptake was 27.7 ppm of aeration.For more Disposal Methods (Complete) data for 2,4-Dinitrophenol (8 total), please visit the HSDB record page. |
| Treatment | There is no specific antidote for 2,4-DNP poisoning. Symptomatic treatment includes replacing oxygen and fluids, controlling temperature by administering sponge baths and ice packs, and using a fan to promote air flow and evaporation. In fully conscious patients, administer cold, sugar-containing liquids by mouth as tolerated. In cases of skin contact, bathe and shampoo contaminated skin and hair promptly. (L179) |
| Wechselwirkungen | 2,4-DNP appears to markedly increase the rate of ethanol metabolism in rat liver slices by 100-160% and in rats in vivo by 20-30%. Because 2,4-DNP uncouples mitochondrial electron transport from oxidative phosphorylation, the oxidation of NADH to NAD+ is accelerated in the mitochondria. Reoxidation of NADH rather than the activity of alcohol dehydrogenase is the rate-limiting step in the metabolism of ethanol, and, therefore, the metabolic effect of 2,4-DNP enhances the clearance of ethanol. Because 2,4-DNP is known to augment the rate of respiration and perspiration, .2.7-8.2% of the initial dose of ethanol was also eliminated by expiration and cutaneous evaporation in the rat.In isolated perfused rat livers, 2,4-DNP caused a depletion of the mitochondrial calcium pool, without altering the extramitochondrial calcium pool. Because 2,4-DNP uncouples oxidative phosphorylation from electron transport by dissipating the electrochemical potential, which provides the energy for the accumulation of calcium in the mitochondrial matrix, only the calcium pool in the mitochondria was affected. 2,4-DNP also caused a rapid increase in NAD, along with a decrease in NADH, a rapid decrease in protein thiol content, but only a slow decrease in nonprotein thiol (e.g., reduced glutathione [GSH]), and an increase in cytoplasmic calcium concentration in isolated rat intestinal cells. This DNP-induced protein thiol loss and/or increase of cytoplasmic calcium concentration induced cell rounding and decreased cell viability. Incubation of salicylate and 2,4-DNP with intestinal cells caused a reduction in the 2,4-DNP-induced increase in cytosolic free calcium concentration by complexation, which facilitated the release of calcium from cells. Salicylate also inhibited DNP-induced cell rounding and increased cell viability in the small intestine.Salicylate (aspirin), which also uncouples oxidative phosphorylation in mitochondrial preparations (although at much higher concentrations than 2,4-DNP), partially inhibited a protein thiol loss induced by 2,4-DNP, but not nonprotein thiol loss by 2,4-DNP in the small intestine of rats. Although DNP inhibits the absorption of the hydrophilic drug, cefmetazole, incubation of DNP and salicylate removed this inhibitory effect in the small intestine. By preventing the DNP-induced protein thiol loss in the small intestine, salicylate appears to enhance diffusivity of cefmetazole in the small intestines. However, salicylate at very high doses can also increase respiratory rates and produce hyperthermia in humans, and possibly exaggerate these signs in persons acutely exposed to 2,4-DNP.Pretreatment of rats with haloperidol significantly diminished the hyperpyrexia and lethality of 2,4-DNP by interfering with the uncoupling of oxidative phosphorylation by 2,4-DNP. The protection by haloperidol may have occurred by an indirect action on the mitochondrial membrane.For more Interactions (Complete) data for 2,4-Dinitrophenol (15 total), please visit the HSDB record page. |
| Zielorgane | Ocular |
| Gesundheitliche Auswirkungen | 2,4-DNP can cause cataracts following ingestion of a small dose for short or long periods. This condition could lead to blindness in both eyes. Breathing in, swallowing, or having skin contact with large amounts of DNP can lead to death.(L168) |
| Ökotoxizitätswerte | LC50Species: Lepomis macrochirus (bluegill)Concentration: 620 ug/L for 96 hr /Conditions of bioassay not specified in source examined/Species: Salmo salar (Atlantic salmon)Concentration: 700 ug/L for 96 hr /Conditions of bioassay not specified in source examined/Species: Mysidopsis bahia (Mysid shrimp)Concentration: 4850 ug/L for 96 hr /Conditions of bioassay not specified in source examined/Species: Herring embryoConcentration: 5,500 ug/L for 96 hr /Conditions of bioassay not specified in source examined/For more Ecotoxicity Values (Complete) data for 2,4-Dinitrophenol (50 total), please visit the HSDB record page. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), a Koc values of 13.5(2) and 16.6(3), indicate that 2,4-dinitrophenol is expected to have very high mobility in soil(SRC). The pKa of 2,4-dinitrophenol is 4.09(4), indicating that this compound will exist almost entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). This can be seen in the measured Koc values(SRC). 2,4-Dinitrophenol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 3.9X10-4 mm Hg at 20 °C(6). A 0% of theoretical BOD using activated sludge in the Japanese MITI test(7) suggests that biodegradation is not an important environmental fate process in soil(SRC). However, the biodegradation half-life of 2,4-dinitrophenol in an acidic soil was reported as 32.1 days and the biodegradation half-life in a basic soil was reported as 4.6 days(8).TERRESTRIAL FATE: 2,4-Dinitrophenol is a moderately weak acid that is expected to be highly labile (leachable and plant available) in high-pH soils. The adsorption and degradation behavior of 2,4-dinitrophenol in two sludge-amended, calcareous soils was determined and used to explain 2,4-dinitrophenol uptake by plants grown in the soils in the greenhouse. The 2,4-dinitrophenol adsorption was minor in both soils and was only slightly affected by sludge. The 2,4-dinitrophenol degradation was rapid in both soils and was unaffected by sludge. Thus, despite limited soil adsorption, plant uptake of 2,4-dinitrophenol was minor in all crops and plant parts owing to rapid soil 2,4-dinitrophenol degradation. Even if a municipal sludge highly contaminated with 2,4-dinitrophenol was identified (an unlikely occurrence), concerns over possible plant contamination should not limit sludge applications to calcareous soils at agronomic rates. Rapid degradation will minimize opportunities for plant uptake of 2,4-dinitrophenol from contaminated soils or leaching of 2,4-dinitrophenol to groundwater given careful water management.AQUATIC FATE: Based on a classification scheme(1), a Koc values of 13.5(2) and 16.6(3), indicate that 2,4-dinitrophenol is not expected to adsorb to suspended solids and sediment(SRC). A pKa of 4.09(4) indicates 2,4-dinitrophenol will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(SRC). According to a classification scheme(5), BCFs of <0.4-0.7 and <3.7(6), suggest the bioconcentration in aquatic organisms is low(SRC). The biodegradation half-life of 2,4-dinitrophenol was reported as 68 days and 2.8 days in aerobic and anaerobic waters, respectively(7).AQUATIC FATE: ... The high solubility of 2,4-dinitrophenol in water (5,600 mg/L at 18 °C) and its presence in solution primarily as an anion strongly favor a partitioning tendency toward water rather than air.For more Environmental Fate (Complete) data for 2,4-Dinitrophenol (6 total), please visit the HSDB record page. |
| Unerwünschte Wirkungen | Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.Nephrotoxin - The chemical is potentially toxic to the kidneys in the occupational setting.Methemoglobinemia - The presence of increased methemoglobin in the bloodthe compound is classified as secondary toxic effectOther Poison - UncouplerDermatotoxin - Skin burns. |
| Expositionspfade | The substance can be absorbed into the body through the skin and by ingestion.Oral (L170)inhalation (L170)dermal (L170) |
| Toxizitätsübersicht | Acute 2,4-dinitrophenol poisoning (from ingestion) involves uncoupling of oxidative phosphorylation, which presumably reduces body's reservoirs of high-energy phosphate. This stimulates oxidative metabolism and, in turn, the heat production of the body. Oxygen consumption, body temperature, respiration and heart rate are all increased. 2,4-Dinitrophenol has been suggested to bind serum proteins such as transthyretin. In fact it was proposed as a therapeutic agent for the prevention/inhibition of amyloid diseases through stabilization of the native fold of transthyretin. (T21, A126, A127) |
| Ökotoxizitätsauszüge | /BIRDS and MAMMALS/ In a study where bobwhite quail were exposed to 2,4-DNP in the diet, 1 of 6 hens in a group consuming 56.1 mg/kg/day died on the eighth and final day of exposure. Necropsy revealed a marked scarcity of subcutaneous fat, reduced visceral fat, and possibly some shrinkage of leg and breast muscles./BIRDS and MAMMALS/ Bobwhite quail were exposed to 2,4-dinitrophenol (DNP) in a respirometer designed to continuously monitor exchange of O2 and CO2, from which metabolic rates (MR) were estimated. After 14-16 days of acclimation to the system (temperature 22 °C, light cycle 8L:14D), hens received feed amended with 0, 625 ppm, or 1250 ppm DNP ad libitum for eight days, followed by 2-5 days of 0 ppm feed. The 625 ppm treatment produced dark period MR 31-41% higher than corresponding control values, and light period MR 23-32% higher than controls. The 1250 ppm treatment produced dark period MR 48-77% higher than control values, and light period MR 41-67% higher than control. Over the eight days of testing, the 625 ppm treatment hens expended 32% more energy than the control hens and hens consuming 1250 ppm feed expended 60% more energy than control hens and lost most of their body fat. In general, the risk of being unable to meet energy demands for survival or reproduction would probably be substantially increased by the observed elevation in MR./BIRDS and MAMMALS/ Ducklings fed 2,4-dinitrophenol at a concentration of 2,500 ppm developed cataracts within 24 hr ... Chickens were also susceptible. Cataract was observed in duckling only 3.5 hr after crop intubation. With no further dosing, the lesion cleared within 3 days./BIRDS and MAMMALS/ The effects of pharmacologically elevated metabolism on respiratory adjustments were studied in chickens. Adult female white leghorn chickens were decerebrated and allowed to recover from anesthesia. In experiment 1, birds were injected with 2.5 mg/kg 2,4-dinitrophenol. Respiratory and cardiovascular measurements were monitored continuously. After steady state conditions were reestablished, another 2.5 mg/kg 2,4-dinitrophenol injection was given and measurements were taken again. Injections and measurements continued until no further oxygen consumption increase occurred. Some birds received a single 5 mg/kg 2,4-dinitrophenol injection. Measurements were repeated every 5 minutes. In experiment 2, birds had control measurements and arterial blood samples taken at approximately 20 °C. Birds were cooled to 2 °C. After a steady respiratory response was established, measurements were taken. Successive 2,4-dinitrophenol doses caused a progressive oxygen consumption increase in the decerebrated chickensa 7.5 to 10 mg/kg dose of 2,4-dinitrophenol elicited the maximal oxygen consumption response, approximately 275% of control values. A single 5 mg/kg 2,4-dinitrophenol injection increased oxygen consumption and the respiratory exchange ratio and increased minute ventilation. Ventilation significantly increased within 10 seconds of the start of 2,4-dinitrophenol injection. A steady state was reached approximately 10 minutes after the start of injection. Birds hyperventilated about 45 minutes after injection when the temperature reached approximately 42.3 °C. The respiratory and cardiovascular effects of the increased metabolism during cold exposure was similar to the initial elevated metabolism responses elicited by 2,4-dinitrophenol. Oxygen consumption increased to approximately 185% of control valuesV1 increased in a way that oxygen extraction remained unchanged. /It was concluded/ that 2,4-dinitrophenol induced hyper metabolism in the decerebrated chiFor more Ecotoxicity Excerpts (Complete) data for 2,4-Dinitrophenol (19 total), please visit the HSDB record page. |
| Plant Concentrations | The phytotoxic nitrophenols were analyzed in beech tree leaves (Fagus sylvatica) from two different alpine forests (Val Gerola and Val Masino) in the Lombardy Region (Northern Italy) which are in decline due to adverse effects of air pollution. Leaves from the more damaged site (Val Gerola) had higher mean total nitrophenol concentrations (313 ng/g) than the Val Masino samples (148 ng/g). 2,4-Dinitrophenol concentrations reported in beach leaves from Val Gerola and Val Masino were 8.2 and 4.1 ng/g dry weight, respectivelysampling was conducted from 1994-1995(1). |
| Signs and Symptoms | See Ingestion.MAY BE ABSORBED! Redness. Roughness. Yellow staining of the skin. Further see Inhalation.Yellow vision. Redness. Conjunctivitis.Nausea. Sweating. Severe thirst. Fever. Increased heart rate. Vomiting. Shock or collapse.Dermal contact may results in redness, roughness, yellow staining of the skin. Nausea, vomiting, palpitations, collapse, sweating occur after inhalation or ingestion. (L170) |
| 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. 2,4-Dinitrophenol is included on this list. Effective date 9/30/91Sunset date: 12/19/95.Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date 9/30/91Reporting date: 11/27/91. |
| FIFRA-Anforderungen | 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. 2,4-Dinitrophenol is found on List B. Case No: 2195Pesticide type: Insecticide, fungicideCase Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.Active ingredient (AI): 2,4-dinitrophenolAI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled." |
| 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. 2,4-Dinitrophenol is included on this list.This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. 2,4-Dinitrophenol is produced, as an intermediate or a final product, by process units covered under this subpart. |
| 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 10 lb or 4.54 kg. The toll free number of the NRC is (800) 424-8802The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b). |
| Clean Water Act Anforderungen | Dinitrophenol 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. /DinitrophenolCAS No. 51-28-5/Toxic pollutant designated pursuant to section 307(a)(1) of the Federal Water Pollution Control Act and is subject to effluent limitations. /Nitrophenols/For the protection of human health from the toxic properties of dinitrophenols ... ingested throughwater and contaminated aquatic organisms, the ambient water criteria /is/ determined to be 70 ug/l ... ingested through contaminated aquatic organisms alone /is/ determined to be 14.3 mg/l ... . /Dinitrophenols/ |
| Landesrichtlinien für Trinkwasser | (AZ) ARIZONA 14 ug/L(FL) FLORIDA 30 ug/L(ME) MAINE 14 ug/L(MN) MINNESOTA 10 ug/L |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 1320 |
| Zollcode | 29089990 |
| RTECS-Nr. | SL2800000 |
| R-Sätze (R) | 23/24/25-33-50-39/23/24/25-11-52/53-1 |
| Toxizität | LD50 (subcutaneous) for rats 25 mg/kg (quoted, RTECS, 1985). |
| Gefahrensymbole | T,N,Xi,F |
| Sicherheitshinweise (S) | 28-37-45-61-28A-36/37-16-7-35 |
| Gefahrenklasse | 4.1Acute Tox. 2 OralAcute Tox. 3 DermalAcute Tox. 3 InhalationAquatic Acute 1Desen. Expl. 4STOT RE 1 |
| Verpackungsgruppe | I |
| Lagerklasse | 4.1B - Flammable solid hazardous materials |
| Gefahrstoffdaten | 51-28-5(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
Das 2,4-Dinitrophenol bildet gelbe, in Wasser unlösliche, in organischen Solvenzien leicht lösliche Kristalle. Die Verbindung wird in der chemischen Technik für eine Vielzahl von Synthesen verwendet (z.B. Pikrinsäure, schwarze Schwefelfarbstoffe). Desweiteren findet die Substanz Anwendung als pH-Indikator im Bereich von pH 2,8 bis 4,0.
Verwenden
2,4-Dinitrophenol (DNP) can be used: As a reactant for catalytic reduction reactions.To activate carboxylic acids by converting them into dinitrophenyl (DNP) esters.To prepare the corresponding ester via acylation reaction using isobutyric anhydride catalyzed by hafnium triflate.As an effective cocatalyst to accelerate the activity and enantioselectivity of primary amine organocatalyst derived from natural primary amino acids for direct asymmetric aldol reaction. As an alternative activator to tetrazoles in the reaction of phosphoroamidites with nucleosides.