| Chemical Abstract Number (CAS #) |
51285
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| Synonyms | 2,4-Dinitrophenol |
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Phenol, 2,4-dinitro |
| Analytical Methods |
EPA Method 604 |
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EPA Method 625 |
EPA Method 8040A |
EPA Method 8250A |
| Molecular Formula | C6H4N2O5 |
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| Use | MFR OF DYES AND DIAMINOPHENOL; WOOD PRESERVATIVE; INSECTICIDE;
AS INDICATOR; AS REAGENT FOR DETECTION OF POTASSIUM & AMMONIUM
IONS.
CHEM INT FOR CI SULFUR BLACK 1, CI SULFUR BLACK 2, PHOTOCHEMICALS &
EXPLOSIVES; ACID-BASE INDICATOR; FUNGICIDE FOR PROTECTION OF
METAL-CUTTING OIL EMULSIONS.
POLYMERIZATION INHIBITOR IN STYRENE PRODUCTION.
2,4-Dinitrophenol is used primarily as a chemical intermediate for the production of azo dyes.
Use in manufacturing of photographic developers.
/SRP: Former use Medication, as dieting aid.
Used as a fungicide on railroad ties, wood poles/posts, wood pilings, and in wood pressure
treatment to prevent wood rot/decay fungi.
Used as an insecticide and miticide for domestic dwellings (outdoor) to control mosquitos.
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| Apparent Color | YELLOWISH TO YELLOW ORTHORHOMBIC CRYSTALS
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| Odor | SWEET, MUSTY ODOR
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| Melting Point | 112-114 DEG C
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| Molecular Weight | 184.11
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| Density | 1.683 g/ml @ 24 DEG C
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| Sensitivity Data | LIQ OR SOLID IRRITANT CHARACTERISTICS: CAUSES SMARTING OF SKIN.
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| Environmental Impact | 2,4-Dinitrophenol may enter the environment in emissions or effluents from
manufacturing plants, mines, foundaries and other facilities at which it is used. It may also be
released in automobile exhaust gas, during its use as a pesticide or as a result of disposal of
products which contain this compound. It may form as a result of photochemical reaction between
benzene and nitrogen monoxide in polluted air. If released to soil 2,4-dinitrophenol is expected to
be highly mobile, although there is a possibility that some of this compound will adsorb to some
clay minerals. 2,4-Dinitrophenol may inhibit microbial growth of some aerobic microbes, but there
are other microorganisms which may degrade this compound in the environment; possible
biotransformation mechanisms include the reduction of the nitro group, hydroxylation of the
aromatic ring and displacement of the nitro group; possible biodegradation products include,
2-amino-4-nitrophenol, 4-amino-2-nitrophenol, and nitrite. 2,4-Dinitrophenol is not expected to
volatilize significantly from wet or dry soil surfaces. If released to water, 2,4-dinitrophenol is
expected to react with alkylperoxy radicals (calculated half-life 58 days) and it has the potential to
photolyze due to absorption of UV light wavelengths > 290 nm. 2,4-Dinitrophenol is not
expected to bioaccumulate in aquatic organisms or volatilize and aerobic biodegradation appears
to be slow. This compound is not expected to adsorb significantly to suspended solids or
sediments, although there is a possibility that some of this compound will adsorb to clay minerals.
If released to air, 2,4-dinitrophenol is expected to exist in both vapor and particulate form. It may
photolyze, it may be physically removed by settling or washout in precipitation or it may react
with photochemically generated hydroxyl radicals (calculated vapor-phase half-life 14 hours). The
most probable route of human exposure to 2,4-dinitrophenol is by inhalation or dermal contact of
workers involved in the manufacture, handling and use of this compound.
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| Environmental Fate | TERRESTRIAL FATE: If released to soil, 2,4-dinitrophenol is expected to be highly
mobile, although there is a possibility that some of this compound will adsorb to some clay
minerals. 2,4-Dinitrophenol may inhibit microbial growth of some aerobic microbes, but there are
soil microorganisms which may degrade this compound in the environment. Possible
biotransformation mechanisms include the reduction of the nitro group; hydroxylation of the
aromatic ring and displacement of the nitro group, possible biodegradation products include
2-amino-4-nitrophenol and 4-amino-2-nitrophenol . 2,4-Dinitrophenol is not expected to
volatilize from soil surfaces.
AQUATIC FATE: If released to water, 2,4-dinitrophenol is not expected to adsorb significantly
to suspended organic solids or sediments, although there is a possiblity that some of this
compound will adsorb to some clay minerals. 2,4-Dinitrophenol has the potential to undergo
direct photolysis due to absorption of UV light wavelengths > 290 nm or it may react with
alkylperoxy radicals (calculated half-life 58 days, . 2,4-Dinitrophenol is not expected to undergo
aerobic biodegradation, bioaccumulate in aquatic organisms or volatilize significantly.
ATMOSPHERIC FATE: If released to the atmosphere, 2,4-dinitrophenol may exist in either
vapor or particulate form. It may undergo direct photolysis due to absorption of UV light
wavelengths > 290 nm, it may be physically removed by settling or washout in precipitation, or it
may react in the vapor phase with photochemically generated hydroxyl radicals (calculated
vapor-phase half-life 14 hours(1,SRC).
The high solubility of 2,4-dinitrophenol in water (5,600 mg/l at 18 deg C) and its presence in
solution primarily as an anion strongly favor a partitioning tendency toward water rather than air.
AQUATIC FATE: Laboratory experiments were performed to investigate the behavior of six
phenols including 2,4-dinitrophenol in dolomite aquifers. The experimental results, with the
exception of the chlorinated phenols, indicate that little, if any, of the phenols adsorb onto
dolomite at temperatures of 5 deg and 22 deg C and at concentrations from 0.1 to 10 mg/l. No
processes of phenol degradation were detected in the experiments, with some experiments lasting
21 days.
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.
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| Drinking Water Impact | During 1980, 2,4-dinitrophenol was detected in sediment/water/soil samples at Love
Canal . 2,4-Dinitrophenol has been monitored at USEPA STORET stations, 812 samples, 0.4%
positive .
EFFL: 2,4-Dinitrophenol has been detected in effluents at USEPA STORET stations, 1311
samples, <2% pos .
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