Grundinformationen
- Standard-SMILES
O=[N+]([O-])c1ccc([N+](=O)[O-])c(O)c1- InChIKey
UWEZBKLLMKVIPI-UHFFFAOYSA-N- Summenformel
- C6H4N2O5
- Durchschnittliche Molmasse
- 184,11 g/mol
- Monoisotopische Masse
- 184,01202123
Namen und Bezeichner
- Bevorzugter Name
- 2,5-Dinitrophenol
- IUPAC
- 2,5-dinitrophenol
- Lokaler Name
- 2,5-Dinitrophenol
- Englischer Name
- 2,5-Dinitrophenol
- Summenformel
- C6H4N2O5
- Molmasse
- 184.11
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
329-71-5- PubChem CID
- 9492
- DTXSID
DTXSID9022021- ChEMBL
CHEMBL107513- ChEBI
CHEBI:40810- UNII
- HSD25Q268Z
- EC Number
- 206-348-1
- Nikkaji
- J53.755A
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,8
- Polarare Oberfläche (TPSA)
- 112 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 5
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 13
- Formalladung
- 0
- Komplexität
- 220
Experimentelle und physikochemische Eigenschaften
Color/Form
Yellow monoclinic prisms or needles from water, ligand
Yellow crystals
Solubility
Soluble in ether, benzene
Slightly soluble in cold alcohol; soluble in hot alcohol, fixed alkali hydroxides
In water, 0.68 g/L
In water, 385 mg/L at 25 °C
Melting Point
226.4 °F (USCG, 1999)
108 °C
MP: also stated as 104 °C
Vapor Pressure
0.000122 [mmHg]
1.22X10-4 mm Hg at 20 °C
Physical Description
2,5-dinitrophenol is a yellow crystalline solid with a sweet musty odor. Sinks and mixes slowly with water. (USCG, 1999)
Yellow solid; [Merck Index] Light yellow crystals; [MSDSonline]
Ionization Efficiency
Negative
0.98
10.5
Agilent XCT
Electrospray ionization
ammonia (10nM)
Physikochemische Eigenschaften
- Schmelzpunkt
- 103 · 103-106 °C(lit.)
- Siedepunkt
- 318.03 °C · 318.03°C (rough estimate)
- Dichte
- 1.7195 · 1.7195 (rough estimate)
- Brechungsindex
- 1.4738 · 1.4738 (estimate)
- Löslichkeit
- Solubility Sparingly soluble in water; soluble in ethanol, ether
- Aggregatzustand
- Solid
- pka
- 5.21 · 5.21, 5.1, 5.0(at 25℃)
- Farbe
- Yellowish needles
- Merck
- 14 · 14,3281
- BRN
- 1913411 · 1913411
- Henry's Law Constant
- 1.5 · 1.5×101 mol/(m3Pa) at 25℃, Schwarzenbach et al. (1988)
- Stabilität
- Light Sensitive
- Major Application
- Liquid crystal films, electrophotographic materials, adhesives, inks, lubricants, preservation of cut flowers, food storage, materials for evaluating dental cariesactivity
- CAS Datenbank
- 329 · 329-71-5(CAS DataBase Reference)
- EPA chemische Informationen
- 2 · 2,5-Dinitrophenol (329-71-5)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Danger
H301: Toxic if swallowed [Danger Acute toxicity, oral];H311: Toxic in contact with skin [Danger Acute toxicity, dermal];H331: Toxic if inhaled [Danger Acute toxicity, inhalation];H373 **: May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure];H411: Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term 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)
Danger
Gefahrenhinweise
Regulatory Information
Phenol, 2,5-dinitro- (wetted with not less than 15% water by mass): HSNO Approval: HSR001274 Approved with controls
The 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.)
Fire Potential
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/
Health Hazards
INHALATION, INGESTION OR SKIN ABSORPTION: Fatigue, thirst, sweating, flushing of face, nausea, vomiting, abdominal pain, diarrhea; restlessness, anxiety, excitement occasionaly leading to convulsions; fever, tachycardia, labored respiration, cyanosis, and sometimes muscle cramps. Loss of consciousness, cessation of breathing and death. EYES: Causes dilation of pupils or posterior subcapsular opacities or cataracts. SKIN: Discoloration, irritation, and dermatitis. (USCG, 1999)
Hazards Summary
Causes first degree burns after brief exposure; [CHRIS] Emergency treatment: see Dinitrophenol. A mucous membrane irritant; Can induce methemoglobinemia; [HSDB] Toxic by inhalation, ingestion, and skin contact; [eChemPortal: ESIS] An irritant; Readily absorbed through skin; May cause liver damage; Disrupts oxidative phosphorylation; [MSDSonline] See Dinitrophenol.
Reactivity Profile
2,5-DINITROPHENOL can detonate or explode when heated under confinement (USCG, 1999). Phenols do not behave as organic alcohols, as one might guess from the presence of a hydroxyl (-OH) group in their structure. Instead, they react as weak organic acids. Phenols and cresols are much weaker as acids than common carboxylic acids (phenol has pKa = 9.88). These materials are incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated, and the heat of the reaction may ignite the gas. Heat is also generated by the acid-base reaction between phenols and bases.
DOT Emergency Guidelines
/GUIDE 113: FLAMMABLE SOLIDS - TOXIC (WET/DESENSITIZED EXPLOSIVE)/ Fire or Explosion: Flammable/combustible material. May be ignited by heat, sparks or flames. DRIED OUT material may explode if exposed to heat, flame, friction or shock; treat 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. /Dinitrophenol, wetted with not less than 15% water/
/GUIDE 113: FLAMMABLE SOLIDS - TOXIC (WET/DESENSITIZED EXPLOSIVE)/ Health: Some are toxic and may be fatal if inhaled, swallowed or absorbed through skin. Contact may cause burns to skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may cause pollution. /Dinitrophenol, wetted with not less than 15% water/
/GUIDE 113: FLAMMABLE SOLIDS - TOXIC (WET/DESENSITIZED EXPLOSIVE)/ Public Safety: CALL Emergency Response Telephone Number. ... Isolate spill or leak area immediately for at least 100 meters (330 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Ventilate closed spaces before entering. /Dinitrophenol, wetted with not less than 15% water/
/GUIDE 113: FLAMMABLE SOLIDS - TOXIC (WET/DESENSITIZED EXPLOSIVE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. /Dinitrophenol, wetted with not less than 15% water/
For more DOT Emergency Guidelines (Complete) data for 2,5-Dinitrophenol (16 total), please visit the HSDB record page.
Sicherheit und Schutzausrüstung
First Aid
Call a doctor.;INHALATION: Remove from contaminated area. Administer oxygen and artificial respiration as needed.;EYES: Flush with water.;SKIN: Wash with soap and water.;INGESTION: Gastric lavage and saline cathartics.;OTHER: If patient is feverish use cold packs and alcohol sponges. (USCG, 1999)
Fire Fighting Procedures
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.
Cleanup Methods
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/
Nonfire Spill Response
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)
Disposal Methods
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.
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/
Preventive Measures
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material wet. Wet spilled material before picking it up. Do not attempt to sweep up dry material. /Dinitrophenol, dry or wetted with less than 15% water by weight/
Evacuation: If the material is on fire or involved in fire consider evacuation of one (1) mile radius. /Dinitrophenol, dry or wetted with less than 15% water by weight/
Personnel protection: Avoid breathing dusts, and fumes from burning material. /Dinitrophenol, dry or wetted with less than 15% water by weight/
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors. /Dinitrophenol solutions/
For more Preventive Measures (Complete) data for 2,5-Dinitrophenol (13 total), please visit the HSDB record page.
Isolation and Evacuation
Excerpt from ERG Guide 113 [Flammable Materials (Wet / Desensitized Explosive)]:;IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area immediately for at least 100 meters (330 feet) in all directions.;LARGE SPILL: Consider initial evacuation for 500 meters (1/3 mile) in all directions.;FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024)
Personal Protective Equipment (PPE)
Self-contained breathing apparatus, butyl rubber gloves, goggles, protective shoes and laboratory coat. (USCG, 1999)
Wear appropriate chemical protective clothing. /Dinitrophenol solutions/
Respirator Selection: Where there is potential for exposure to dinitrophenol, use a NIOSH/MSHA approved supplied-air respirator with a full facepiece operated in the positive pressure mode, or with a full facepiece, hood, or helmet in the continuous flow mode; or use a NIOSH/MSHA approved self-contained breathing apparatus with a full facepiece operated in pressure-demand or other positive pressure mode.
People exposed to the solid, or to a strong soln should wear protective clothing, hand protection, and, in confined spaces, the use of respiratory protective equipment. /Dinitrophenol/
Toxikologische Informationen
Interactions
The relative potencies of the 6 dinitrophenols in uncoupling phosphorylation in rat liver mitochondria were in declining order 3,5-dinitrophenol, 2,4-dinitrophenol 2,6-dinitrophenol and 3,4-dinitrophenol and 2,3-dinitrophenol and 2,5-dinitrophenol. The relative potency of these phenolic compounds may be determined primarily by their ability to cross a boundary membrane and to bind to a cationic site on a protein normally associated with energy-conservation, rather than merely by their relative acidity or lipid solubility.
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 460(SRC), determined from a structure estimation method(2), indicates that 2,5-dinitrophenol is expected to have moderate mobility in soil(SRC). The pKa of 2,5-dinitrophenol is 5.21(3), indicating that this compound will exist almost entirely 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(4). Volatilization from moist soil is not expected because 2,5-dinitrophenol exists as an anion and anions do not volatilize(SRC). 2,5-Dinitrophenol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.22X10-4 mm Hg at 20 °C(5). No biodegradation was observed when 2,5-dinitrophenol was incubated with an anaerobic digester sludge over a 90 day period(6). 2,5-Dinitrophenol was stable to biochemical degradation by a mixed culture of phenol-adapted bacteria under aerobic conditions(7).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 460(SRC), determined from a structure estimation method(2), indicates that 2,5-dinitrophenol is expected to adsorb to suspended solids and sediment(SRC). A pKa of 5.21(3) indicates 2,5-dinitrophenol will exist almost entirely 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(4), an estimated BCF of 7(SRC), from its log Kow of 1.73(5) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). No biodegradation was observed when 2,5-dinitrophenol was incubated with an anaerobic digester sludge over a 90 day period(7). 2,5-Dinitrophenol was stable to biochemical degradation by a mixed culture of phenol-adapted bacteria under aerobic conditions(8).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,5-dinitrophenol, which has a vapor pressure of 1.22X10-4 mm Hg at 20 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,5-dinitrophenol 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 32 days(SRC), calculated from its rate constant of 5.0X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 2,5-Dinitrophenol may react with nitrate radicals in the atmosphere(2). 2,5-Dinitrophenol absorbs light at wavelengths of 361 nm in water(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).
Adverse Effects
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 blood; the compound is classified as secondary toxic effect;Other Poison - Uncoupler;Dermatotoxin - Skin burns.
Ecotoxicity Excerpts
/AQUATIC SPECIES/ The response of the water receptor of frogs was repressed by nitrophenol derivatives. The order of reversible inhibitory action of the derivatives was 2,4-dinitrophenol (I) > 2,5-dinitrophenol > 2,4,6-trinitrophenol > p-nitrophenol > 2,6-dinitrophenol > m-nitrophenol > o-nitrophenol.
/AQUATIC SPECIES/ A comparison was made between the predicted 96-hr guppy median lethal concn of 110 phenols based upon quant structure-activity relationship (QSAR) equations of J Saarikoski and M Viluksela (1982) and the data from 936 toxicity screening tests for these chems. Test data on up to 8 species of freshwater fishers were available per cmpd. Overall, the experimental toxicity data on these chem were consistent with the QSAR predictions. The 110 phenols occupy a considerably larger range of spanned substituent space than the QSAR training set. One cmpd, 4-aminophenol exhibited lethality at test concn of 35 times below that predicted. The increased fish toxicity of this cmpd is explained in terms of a proelectrophilic mol mechanism, in which the parent cmpd is metabolically oxidized to a para quinoid structure. The resulting electrophilic metabolite is susceptible to attack by nucleophilic moieties present in biological macromols leading to covalent bond formation and inhibition of biochem processes.
/AQUATIC SPECIES/ The 96-hr median lethal concn (LC50) of 21 substituted phenols (I, R= H, alkyl, Cl, or NO2; R1= H, Cl, OH, methoxy, alkyl, or NO2; n= 0-5; m= 0 to 5-n) for the guppy (Poecilia reticulata) were detd at pH 6-8 and related to the lipohilicity defined as log P from the 1-octanol/water system, and to the DELTApKa value (pKa of phenol - pKa). Log P was the more important parameter and exhibited a good correlation with log (1/LC50) at all pH levels. The contribution of DELTApKa when introduced as a 2nd parameter into the regression equation was dependent on the pH of water: at pH 6, it was pos but turned neg as the pH was raised to 8. If the LC50 were correlated for ionization using an empirically formulated relation between toxicity and pH, the resulting regression equation could be used to predict the toxicity at any pH from 6 to 8. When corrected for ionization, log BCF (the bioconcn factor) of 8 phenols was highly correlated with log P but not with DELTApKa. The regression of log BCF on log P sufficed to explain the regression of toxicity on lipophilicity.
/AQUATIC SPECIES/ The effects of the uncoupling reagents 2,4- and 2,5-dinitrophenol (DNP) on the ontogenesis of herring (Culpea harengus) were investigated. Eggs of the Baltic spring and autumn spawning herring were artificially fertilized, attached to glass plates and incubated in 1-L aerated containers (14 to 16% water salinity) for 30, 48 or 55 hr prior to incubation in 0.005, 0.01, 0.015, 0.02, 0.025, 0.03, 0.05, 0.075 and 0.10 mM 2,4- or 2,5-DNP/l. The solution temperatures were maintained at about 10.8 and 11.8 °C for the spring and autumn spawners, respectively. The effects of the DNP concentrations on the embryonic development were determined by measuring the activity of the embryo, the heartbeat rate and the mutagenic and mortality rates. The rate of mortality was shown to be dependent on the age of the embryo at the start of exposure and on the concentration of the DNP. Exposure at 30 and 48 hr resulted in 100% mortality at 0.025 and 0.03 mM/l, respectively. When the embryos were first exposed at 55 hr, highest concentration (0.10 mM DNP/l) produced 92.6% mortality. DNP also increased the occurrence of malformations which were in the form of anophthalmy, symmetrical and unilateral microphthalmy, curled bodies and dedifferentiations.
For more Ecotoxicity Excerpts (Complete) data for 2,5-Dinitrophenol (8 total), please visit the HSDB record page.
Medical Surveillance
In exposed workers, blood concentration of /dinitro-derivatives/ should not exceed 10 ug/g. A white cell count should be performed if the exposed person has an unexplained persistent fever. Individuals who have a fall in white blood cell counts should avoid further exposure. /Dinitro-derivatives/
Consider skin, eyes, thyroid, blood, central nervous system, liver and kidney function, as well as general health in placement and periodic examination. Dinitrophenols can be measured in urine as such or as an aminophenol.
/Workers/ regularly exposed to dinitrophenol should have their urine tested regularly for dinitrophenol or amino-nitrophenol by polarography or Derrien's test. /Dinitrophenol/
Soil Adsorption/Mobility
Using a structure estimation method based on molecular connectivity indices(1), the Koc of 2,5-dinitrophenol can be estimated to be 460(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2,5-dinitrophenol is expected to have moderate mobility in soil. The pKa of 2,5-dinitrophenol is 5.21(3), indicating that this compound will exist almost entirely 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(4).
Human Toxicity Excerpts
/SIGNS AND SYMPTOMS/ Short Term Exposure: Dinitrophenol can affect you when breathed and by passing through skin ... May affect the metabolism, causing very high body temperature. May affect the peripheral nervous system causing numbness, "pins and needles," and/or weakness of the hands and feet. Exposure can cause a bluish color to skin and lips, headaches, temperature rise, dizziness, collapse, convulsions, coma, and even death. Exposure may irritate the lungs, causing caoughing and shortness of breath. Higher levels can cause a build up of fluid in the lungs, a medical emergency which can cause death. Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis with rash and drying and itching of the skin. Dinitrophenol may have effects on the dyes, causing cataracts. Exposure can damage the liver and kidneys, and affect the thyroid gland. May cause lung irritation and the development of bronchitis with coughing and shortness of breath. May damage the nervous system. High exposure may damage the developing fetus.
/SIGNS AND SYMPTOMS/ 2,4-dinitrophenol does not produce methemoglobin, but the 2,3-, 2,5-, 2,6-, and 3,4-isomers do produce it.
Environmental Biodegradation
The ... wastewaters (COD 4.4-6 g/L) contained nitrobenzene and 2,4-dinitrophenol. These compounds are biodegradable ... and account for 50% of the Chemical Oxygen Demand. The remainder of the Chemical Oxygen Demand reflects the presence of ... 2,5- and 2,6-dinitrophenol, which are not biodegradable.
AEROBIC: 2,5-Dinitrophenol was stable to biochemical degradation by a mixed culture of phenol-adapted bacteria under aerobic conditions (0% COD chemical oxygen demand) removal after 20 days)(1).
AEROBIC: A low degree of degradability was observed for 2,5- and 2,6-dinitrophenol, whereas 2,4-dinitrophenol was readily degraded /by adapted activated sludge/.
ANAEROBIC: No biodegradation was observed when 2,5-dinitrophenol was incubated with an anaerobic digester sludge over a 90 day period(1).
Environmental Bioconcentration
An estimated BCF of 7 was calculated in fish for 2,5-dinitrophenol(SRC), using a log Kow of 1.75(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
Volatilization from Water/Soil
A pKa of 5.21(1) indicates 2,5-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). 2,5-Dinitrophenol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.22X10-4 mm Hg(2).
Regulatorische Informationen
Regulatory Information
Phenol, 2,5-dinitro- (wetted with not less than 15% water by mass): HSNO Approval: HSR001274 Approved with controls
The 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.)
CERCLA Reportable Quantities
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) 424-8802; The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).
Clean Water Act Requirements
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. /Dinitrophenol; CAS 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/
Sicherheitsdaten
- wgk
- 3
- ridadr
- UN 1320 (DINITROPHENOL, WETTED with not less than 15 % water, by mass)
- hs_code
- 29089990
- RTECS-Nr.
- SL2900000
- risk_code
- 23/24/25-33-51/53
- hazard_code
- T,N
- safety_code
- 28-37-45-61
- hazard_class
- 4.1
- packing_group
- I
- Giftige Stoffe Daten
- 329-71-5(Hazardous Substances Data)
Chemie und Industrie
Pharmakologische Informationen
Mechanism of Action
... /Of/ the six isomeric dinitrophenols, those with nitro groups in the 2,4- and 3,4-positions stimulate oxygen consumption, whereas those with nitro groups in the 2,5-position do not. ...
2,4-Dinitrophenol induced calcium-dependent secretion of adrenaline from the perfused adrenals of the rabbits. Secretion of adrenaline was accompanied by that of dopamine-beta-hydroxylase, showing the exocytotic nature of the process. 2,4,6-Trinitrophenol, which is devoid of uncoupling activity, and other nitrophenol cmpd were also effective in inducing secretion, suggesting that secretion by nitrophenol cmpd is due to increased Ca entry through its direct effect on the plasma membrane.
All nitrophenols inhibit the microbial growth of natural aquatic systems because they uncouple the metabolic process of oxidative phosphorylation. /Nitrophenols/
Metabolism/Metabolites
Metabolites of 2,5-Dinitrophenol: 2-amino-5-nitrophenol, 5-amino-2-nitrophenol, 2,5-diaminophenol /From table/
2,5-dinitrophenol /forms/ 2-amino-5-nitrophenol and 5-amino-2-nitrophenol probably in Pseudomonas.
2,4-Dinitrophenol (2,4-DNP), 2,5-dinitrophenol (2,5-DNP), 2,6-dinitrophenol (2,6-DNP) were compared with respect to stimulation of ventilation and oxygen consumption. In all experiments, 3-4 mg/kg of 1 dinitrophenol isomer was administered to chloralose anesthetized dogs by intraarterial infusion. ... 2,5-DNP elicited small increments in both ventilation and oxygen consumption.
A study was made of the distribution of glutathione-S-transferase activity toward various nitro compounds in monkey tissues and the action of a purified monkey liver glutathione-S-transferase toward various nitro compounds including carcinogenic substances. The liver, kidney and small intestine demonstrated particularly high levels of activity when compounds such as 4-nitroquinoline-N-oxide (56575), 5-nitrofurfural-diacetal and o-dinitrobenzene (99650) were used as substrates. Fifty-two nitro compounds, including 19 nitrofuran derivatives, were also used to test the nitrite releasing activity of the major enzyme purified from rhesus-monkey. The purified enzyme showed activity only toward o-dinitrobenzene, 4-nitroquinoline-N-oxide, 3,4-dinitrobenzoic-acid (528450), p-dinitrobenzene (100254), 2,5-dinitrobenzoic-acid (610286), 2,5-dinitrophenol (329715), tetra-chloronitrobenzene, and 2,4-dinitrobenzoic-acid (610300) of the 33 nitro compounds other than nitrofuran derivatives which were tested as substrates.
Absorption, Distribution and Excretion
/The investigators/ ... studied the pharmacokinetics of ... dinitrophenol isomers /incl 2,5-dinitrophenol/ and showed that elimination from the blood of mice, rabbits, guinea pigs, rats, and monkeys was complete within 30 hr.
Absorption of dinitro compounds can take place with ease through the lungs, the gut, or the intact skin. The rate of absorption through skin is likely to be greater when the substances are applied in oily rather than aq soln. /Dinitro cmpd/
... Dinitro compounds are persistent yellow dye-stuffs, staining exposed skin, hair, wool, fur, and feathers a distinct yellow or orange color which remains obvious for weeks or even months afterwards, despite the action of water and weather. Such staining provides evidence of at least external contact with the chemicals. /Dinitro cmpd/
Verwendung und Herstellung
Uses
Used as an indicator and to make dyes and other organic chemicals; [Merck Index]
In manufacture of dyes and organic chemicals, as an indicator.
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