2,5-Dinitrophenol

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)

H301 (97.7%): Toxic if swallowed [Danger Acute toxicity, oral]

H311 (97.7%): Toxic in contact with skin [Danger Acute toxicity, dermal]

H331 (97.7%): Toxic if inhaled [Danger Acute toxicity, inhalation]

H373 (97.7%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]

H411 (100%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Aggregated GHS information provided per 43 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

H373: May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]

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 Extinguishing Agents: Water, dry chemical, CO2, foam. (USCG, 1999)

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.

The primary hazard is from blast effect where the entire load can explode instantaneously and not from flying projectiles and fragments. /Dinitrophenol, dry/

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)

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/

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/

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.

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)

/Dinitrophenol/ ... should be stored in a cool ventilated place away from area of acute fire hazard and away from powerful oxidizing agents. /Dinitrophenol/

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/

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]

Yellow monoclinic prisms or needles from water, ligand

Yellow crystals

226.4 °F (USCG, 1999)

MP: also stated as 104 °C

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

1.68 (USCG, 1999) - Denser than water; will sink

0.000122 [mmHg]

1.22X10-4 mm Hg at 20 °C

log Kow= 1.75

Appear to be stable in acid solution, but are susceptible to decomposition by uv radiation in alkaline solutions. /Dinitrophenols/

When heated to decomposition it emits toxic fumes of /nitrogen oxides/.

pH range: 4.0 colorless, 5.4 yellow

Negative

Agilent XCT

Electrospray ionization

ammonia (10nM)

MeCN (80%)

DOI:10.1021/acs.analchem.7b00595

Detection: 2.4 mg/L

pKa = 5.21 at 25 °C

Heat of fusion: 30.80 cal/g = 128.87 J/g = 23,726 J/mol

13C nuclear magnetic resonance spectrum

Boiling point

Chemical shift

Diffusion

Electron conductivity

Fluorescence

Fusion temperature

Heat of sublimation

Kinetic properties

Melting temperature

Phase transition

Spin-spin coupling constant

Transition enthalpy

Vapor pressure

Slowly mixes with water.

Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic

Phenols and Cresols

Explosive

Strong Oxidizing Agent

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.

Contact with reducing agents, combustibles may cause fire and explosions. Forms shock-sensitive explosive salts with ammonia, strong bases, and most metals. May accumulate static electrical charges /which/ may cause ignition of its vapors.

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.

LD50 Rat ip 150 mg/kg

LD50 Mouse ip 273 mg/kg

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.

Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Dinitrophenol and Related Compounds/

Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for shock and treat if necessary ... . Monitor for pulmonary edema and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination. flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . Cover skin burns with dry sterile dressings after decontamination ... . Rapid body cooling may be necessary in case of hyperthermia. Salicylates are contraindicated. /Dinitrophenol and Related Compounds/

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of 0.9% saline (NS) or lactated Ringer's (LR) /SRP: "To keep open", minimal flow rate/. For dehydration and hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Dinitrophenol and Related Compounds/

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/

/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.

/OTHER TOXICITY INFORMATION/ ... The nitrite-releasing activity of the major enzyme purified from rhesus monkey liver was tested on fifty-two nitro compounds including nineteen nitrofuran derivatives. Among the thirty-three nitro compounds other than the nitrofuran derivatives tested as substrates, the purified enzyme showed activity only toward o-dinitrobenzene, 4-nitroquinoline N-oxide, 3,4-dinitrobenzoic acid, p-dinitrobenzene, 2,5-dinitrobenzoic acid, 2,5-dinitrophenol, tetra-chloronitrobenzene and 2,4-dinitrobenzoic acid. The crude supernatant fraction of rhesus monkey liver showed activity in substrate specificity roughly similar to that of the purified enzyme. On the other hand, among at least ten carcinogenic 2-substituted 5-nitrofran derivatives tested, 4,6-diamino-2-(5-nitro-2-furyl)-s-triazine, 5-nitro-2-furaldehyde semicarbazone, N-[[3-(5-nitro-2-furyl)-1,2,4-oxadiazol-5-yl]methyl] acetamide, and N-[5-(5-nitro-2-furyl)-1-3,4-thiadiazol-2-yl)acetamide were shown to be enzymatically conjugated with reduced glutathione. Among the other nine 2-substituted 5-nitrofuran derivatives tested, six compounds could be the substrates of the enzyme, and 5-nitrofurfural and 5-nitrofurfural diacetal were especially good substrates. There was, however, little apparent correlation between their carcinogenicity and susceptibility to glutathione S-transferase. The bulky substituents at position 2 appeared to decrease the susceptibility of these nitrofuran derivatives to the enzyme. Both Vmax and Km values of the purified enzyme varied greatly among the substrates, and the optimum pH fell between 7.5 and 9.0 in most cases.

/OTHER TOXICITY INFORMATION/ The signs of intoxication are much the same in all species and include listlessness, loss of appetite and activity, deepened and more rapid respiration, sweating (in some animals only), thirst, oliguria, muscular weakness, prostration, dyspnea, and death, with terminal hyperpyrexia. Signs may appear within a few min if large amt have been ingested, otherwise they may be delayed for several hr. /Dinitro cmpd/

/OTHER TOXICITY INFORMATION/ Cancer culture medium significantly decreased the number of multinucleated tumor cells. Janus Green B, 2,5-dinitrophenol, or malonate abolished this effect. Thymidine 5'-triphosphate at 0.58 mmol/mL or thymidine 5'-monophosphate also induced the cleavage of tumor cells. ATP, GTP, CTP, and UTP had no such effect. Thymine and thymidine were inactive. ATP and thymidine together caused cytokinesis in multinucleated cells. Intraperitoneal administration of oxalacetate, 25 ug/hamster, or malonate, 25 ug/hamster, caused an increase in number of multinucleated cells in hamster ascites tumor and Ehrlich tumor in vivo.

LC50; Species: Pimephales promelas (Fathead minnow, age 26-34 days juveniles); Conditions: freshwater, flow through, 25 °C, pH 7.8, hardness 45 mg/L CaCO3, alkalinity 42 mg/L CaCO3; Concentration: 3360 ug/L for 96 hr /> or = 95% purity/

/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.

2,5-Dinitrophenol's production and use in the manufacture of dyes and as an indicator may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 1.22X10-4 mm Hg at 20 °C indicates 2,5-dinitrophenol will exist solely as a vapor in the atmosphere. Vapor-phase 2,5-dinitrophenol will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 32 days. 2,5-Dinitrophenol may react with nitrate radicals in the atmosphere. 2,5-Dinitrophenol absorbs light at wavelengths of 361 nm in water and therefore may be susceptible to direct photolysis by sunlight. If released to soil, 2,5-dinitrophenol is expected to have moderate mobility based upon an estimated Koc of 460. The pKa of 2,5-dinitrophenol is 5.21, 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. Volatilization from moist soil is not expected because 2,4-dinitrophenol exists as an anion and anions do not volatilize. No biodegradation was observed when 2,5-dinitrophenol was incubated with an anaerobic digester sludge over a 90 day period. 2,5-Dinitrophenol was stable to biochemical degradation by a mixed culture of phenol-adapted bacteria under aerobic conditions. If released into water, 2,5-dinitrophenol is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon 2,5-dinitrophenols pKa. An estimated BCF of 7 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Occupational exposure to 2,5-dinitrophenol may occur through inhalation and dermal contact with this compound at workplaces where 2,5-dinitrophenol is produced or used. Use data indicate that the general population may be exposed to 2,5-dinitrophenol via dermal contact with products containing 2,5-dinitrophenol. (SRC)

2,5-Dinitrophenol's production and use in the manufacture of dyes and as an indicator(1) may result in its release to the environment through various waste streams(SRC).

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).

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).

The rate constant for the vapor-phase reaction of 2,5-dinitrophenol with photochemically-produced hydroxyl radicals has been estimated as 5.0X10-13 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 32 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2,5-Dinitrophenol may react with nitrate radicals in the atmosphere(1). The pKa of 2,5-dinitrophenol is 5.21(2), indicating that this compound will exist almost entirely in anion form in the environment. 2,5-Dinitrophenol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). 2,5-Dinitrophenol absorbs light at wavelengths of 361 nm in water(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

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).

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).

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).

SURFACE WATER: The results of a monitoring program in surface waters located in agricultural areas throughout the Netherlands with respect to these nitrophenols are presented. Medinoterb and 2,3-, 2,5-, and 2,6-dinitrophenol were not found in any of the water samples. The frequency of occurrence in water samples was low for all nitrophenols.

Those involved in dye manufacture, picric acid manufacture, photographic chemicals.

LC50; Species: Pimephales promelas (Fathead minnow, age 26-34 days juveniles); Conditions: freshwater, flow through, 25 °C, pH 7.8, hardness 45 mg/L CaCO3, alkalinity 42 mg/L CaCO3; Concentration: 3360 ug/L for 96 hr /> or = 95% purity/

/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.

2,5-Dinitrophenol's production and use in the manufacture of dyes and as an indicator may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 1.22X10-4 mm Hg at 20 °C indicates 2,5-dinitrophenol will exist solely as a vapor in the atmosphere. Vapor-phase 2,5-dinitrophenol will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 32 days. 2,5-Dinitrophenol may react with nitrate radicals in the atmosphere. 2,5-Dinitrophenol absorbs light at wavelengths of 361 nm in water and therefore may be susceptible to direct photolysis by sunlight. If released to soil, 2,5-dinitrophenol is expected to have moderate mobility based upon an estimated Koc of 460. The pKa of 2,5-dinitrophenol is 5.21, 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. Volatilization from moist soil is not expected because 2,4-dinitrophenol exists as an anion and anions do not volatilize. No biodegradation was observed when 2,5-dinitrophenol was incubated with an anaerobic digester sludge over a 90 day period. 2,5-Dinitrophenol was stable to biochemical degradation by a mixed culture of phenol-adapted bacteria under aerobic conditions. If released into water, 2,5-dinitrophenol is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon 2,5-dinitrophenols pKa. An estimated BCF of 7 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Occupational exposure to 2,5-dinitrophenol may occur through inhalation and dermal contact with this compound at workplaces where 2,5-dinitrophenol is produced or used. Use data indicate that the general population may be exposed to 2,5-dinitrophenol via dermal contact with products containing 2,5-dinitrophenol. (SRC)

2,5-Dinitrophenol's production and use in the manufacture of dyes and as an indicator(1) may result in its release to the environment through various waste streams(SRC).

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).

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).

The rate constant for the vapor-phase reaction of 2,5-dinitrophenol with photochemically-produced hydroxyl radicals has been estimated as 5.0X10-13 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 32 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2,5-Dinitrophenol may react with nitrate radicals in the atmosphere(1). The pKa of 2,5-dinitrophenol is 5.21(2), indicating that this compound will exist almost entirely in anion form in the environment. 2,5-Dinitrophenol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). 2,5-Dinitrophenol absorbs light at wavelengths of 361 nm in water(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

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).

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).

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).

SURFACE WATER: The results of a monitoring program in surface waters located in agricultural areas throughout the Netherlands with respect to these nitrophenols are presented. Medinoterb and 2,3-, 2,5-, and 2,6-dinitrophenol were not found in any of the water samples. The frequency of occurrence in water samples was low for all nitrophenols.

Those involved in dye manufacture, picric acid manufacture, photographic chemicals.

Occupational exposure to 2,5-dinitrophenol may occur through inhalation and dermal contact with this compound at workplaces where 2,5-dinitrophenol is produced or used. Use data indicate that the general population may be exposed to 2,5-dinitrophenol via dermal contact with products containing 2,5-dinitrophenol. (SRC)

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/

/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.

UN 0076; Dinitrophenol, dry or wetted with less than 15% water, by mass[United Nations; Recommendations on the Transport of Dangerous Goods. Model Regulations. Vol. I, 16th Revised Edition (2009). Available from, as of November 22, 2010: http://www.unece.org/trans/danger/publi/unrec/rev16/16files_e.html]

UN 1320; Dinitrophenol, wetted with not less than 15% water, by mass[United Nations; Recommendations on the Transport of Dangerous Goods. Model Regulations. Vol. I, 16th Revised Edition (2009). Available from, as of November 22, 2010: http://www.unece.org/trans/danger/publi/unrec/rev16/16files_e.html]

UN 1599; Dinitrophenol solution[United Nations; Recommendations on the Transport of Dangerous Goods. Model Regulations. Vol. I, 16th Revised Edition (2009). Available from, as of November 22, 2010: http://www.unece.org/trans/danger/publi/unrec/rev16/16files_e.html]

Hazard Class or Division: 1.1D; Dinitrophenol, dry or wetted with less than 15% water, by mass[United Nations; Recommendations on the Transport of Dangerous Goods. Model Regulations. Vol. I, 16th Revised Edition (2009). Available from, as of November 22, 2010: http://www.unece.org/trans/danger/publi/unrec/rev16/16files_e.html]

For more Shipping Name/ Number DOT/UN/NA/IMO (Complete) data for 2,5-Dinitrophenol (6 total), please visit the HSDB record page.

49 166 26; Dinitrophenol solution (shipped water wet with at least 15% water)

49 214 25; Dinitrophenol solution

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./

The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.

The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Flammable Solid Poison