| | Dinitrophenol,dry or wetted with less than 15% water,by mass Basic information |
| | Dinitrophenol,dry or wetted with less than 15% water,by mass Chemical Properties |
| Melting point | 86°C | | Boiling point | 318.03°C (rough estimate) | | density | 1.6800 | | refractive index | 1.4738 (estimate) | | EPA Substance Registry System | Dinitrophenol (25550-58-7) |
| | Dinitrophenol,dry or wetted with less than 15% water,by mass Usage And Synthesis |
| Description | Dinitrophenol (DNP) was first introduced in the United States
in 1933 as a treatment for obesity but was removed from the
market in 1938 due to several fatalities and occurrences of
cataracts. | | Uses | DNPs are used as fungicides, herbicides, or insecticides. The
fungicidal, herbicidal, or insecticidal properties depend on
minor differences in the chemical structures of the different
DNP compounds, and several DNP compounds have more
than one pesticidal use. The pesticidal use of one DNP, Dinoseb,
was eliminated in the United States in 1986. While there
has been a cancellation of all United States registrations for the
fungicide/miticide Dinocap, it still has agricultural uses
worldwide. DNPs have also been used in the production of
dyes, explosives, and photographic developing fluids. | | Definition | ChEBI: 2,3-dinitrophenol is a dinitrophenol. | | General Description | A yellow colored liquid dissolved in an organic solvent. The flammability of the solution depends on the solvent. Dinitrophenol itself is combustible though Dinitrophenol,dry or wetted with less than 15% water,by mass may require some effort to ignite. Toxic by skin absorption and inhalation. Prolonged exposure to fire or heat may result in the spontaneous decomposition and heating with a resultant explosion. Produces toxic oxides of nitrogen during combustion. | | Air & Water Reactions | Slightly soluble in water. | | Reactivity Profile | DINITROPHENOL SOLUTION serves as a slight to strong oxidizing agent. If mixed with reducing agents, including hydrides, sulfides and nitrides, may begin a vigorous reaction that culminates in a detonation. May explode in the presence of a base such as sodium hydroxide or potassium hydroxide. Severe explosion hazard when dry. | | Health Hazard | TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. | | Fire Hazard | Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. 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. | | Safety Profile | Poison by ingestion and
subcutaneous routes. An explosive and
flammable solid. When heated to
decomposition it emits toxic fumes of NOx.
See also NITRO COMPOUNDS of
AROMATIC HYDROCARBONS. | | Environmental Fate | The uses of DNPs indicate that they may be released into the
environment. DNPs are expected to have moderate to high
mobility in soil based on an estimated Koc value of 460.
Mobility will be particularly evident in moist soils, since DNPs
will exist primarily as anions. If released into water, DNPs will
largely remain in solution and not adsorb significantly to
particulate matter or sediment. Volatilization of DNPs from
soil or water is not expected to be a significant fate process due
to Henry’s law constants ranging from 2.8 ×10-8 to
8.6 × 10-8 m3 atm mol-1. DNPs are not known to undergo
hydrolysis in the environment, although photolysis may be an
important abiotic degradation process. Log Kow values ranging
from 1.37 to 1.75 and bioconcentration factors of <6.6 in fish
suggest that accumulation in aquatic organisms is low. | | Toxicity evaluation | DNPs act as uncouplers of oxidative phosphorylation; these
compounds reduce the electrochemical (proton) gradient
necessary for oxidative phosphorylation by releasing phenolic
protons in the mitochondrial matrix. The energy produced due
to oxidation is not utilized for the synthesis of ATP but elevates
body temperature, which can lead to fatal hyperpyrexia.
Oxygen consumption, body temperature, breathing rate, and
heart rate are increased following exposure to toxic levels of
DNPs. Permeability of mitochondrial membranes to hydrogen
ions was found to be increased with the failure of conversion of
ADP to ATP. Inefficient circulation and respiration cannot meet
the increased metabolic demand, resulting in anoxia and acidosis. Fat serves as an alternative fuel for metabolism.
Weight loss occurs as a result of inhibition of lipogenesis from
pyruvate and lactate following exposure to DNPs. |
| | Dinitrophenol,dry or wetted with less than 15% water,by mass Preparation Products And Raw materials |
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