1,4-Dinitrobenzene
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1,4-Dinitrobenzene
structure -
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CAS No:
100-25-4
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Formula:
C6H4N2O4
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Chemical Name:
1,4-Dinitrobenzene
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Synonyms:
Benzene,1,4-dinitro-;Benzene,p-dinitro-;1,4-Dinitrobenzene;p-Dinitrobenzene;Para-dinitrobenzene;NSC 3809;1,4-Dintrobenzene
- Categories:
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CAS No:
Description
light yellow powderChEBI: A dinitrobenzene carrying nitro groups at positions 1 and 4.Colorless to yellow solid. Sinks and mixes slowly with water.Clear, colorless to white crystalline solid or monoclinic crystals. Slowly turns yellow on exposure to air.
P-dinitrobenzene is a colorless to yellow solid. Sinks and mixes slowly with water. (USCG, 1999)|WHITE-TO-PALE-YELLOW CRYSTALS.|Pale-white or yellow solid.
P-dinitrobenzene is a colorless to yellow solid. Sinks and mixes slowly with water. (USCG, 1999)|1,4-dinitrobenzene is a dinitrobenzene carrying nitro groups at positions 1 and 4.
1,4-Dinitrobenzene Basic Attributes
168.11
168.11
1105828
202-833-7
784Q9O56S9
0692
3809
3443|1597
DTXSID0021836
White crystals|Colorless to yellow monoclinic needles|Pale white or yellow, crystalline or solid.
29042090
Characteristics
91.6
1.46/1.49
Ochre to orange Crystals or Powder
1.625 g/cm3 @ Temp: 18 °C
174 °C
297 °C
150 °C
1.725 (589.3 nm)
soluble in water. (0.8 g/L) at 20°C.alcohol: soluble 1g in 300ml
2-8°C
Vapour pressure, kPa at 20°C:
Relative vapour density (air = 1): 5.8
Oral-Rat LDL0: 50 mg/kg; Celiac-rat LD50: 56 mg/kg
Inflammable in case of open flame, high temperature, oxidant; burning produces toxic nitrogen oxide fumes
Mixture with nitric acid is a high explosive.
Sublimable|Heat of fusion: 39.99 cal/g
Slowly mixes with water.
Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic
Explosive
All three isomers have similar properties and may react vigorously with oxidizing materials. Their reaction with nitric acid (nitration) will lead to a mixture of trinitrobenzenes possessing high-explosive properties [Urbanski, 1967, vol. 3, p. 290]. If heat and reaction conditions of the nitration are not controlled, detonation comparable to TNT may occur [Anon., J. R. Inst. Chem., 1960, 84, p. 451]. Mixture of 1,3-dinitrobenzene with tetranitromethane was found highly explosive [Urbanski, 1964, vol. 1, 592]. 1,2-dinitrobenzene is a severe explosion hazard when shocked or exposed to heat or flame. When heated to decomposition all dinitrobenzens emit toxic fumes of nitrogen oxides [Sax, 9th ed., 1996, p. 1374].
10.50 eV
Combustible Solid
Dust explosion possible if in powder or granular form, mixed with air.
Liquid dinitrobenzene will attack some forms of plastics, rubber, and coatings. /Dinitrobenzene, all isomers/
Safety Information
II
6.1
UN 3443 6.1/PG 2
3
26/27/28-33-34-50/53-52/53-39/23/24/25-23/24/25-11
28-36/37-45-60-61-16
CZ7525000
T+,N,T,F
Storehouse ventilated at low temperature and dry; impact-proof; stored separately from oxidant
Explosive when mixed with oxidant; explode upon impact
Stable, but may be shock-sensitive. May explode if heated. Incompatible with oxidizing agents, strong bases, nitric acid, many metals, tin oxides.
P260-P264-P273-P280-P284-P301 + P310
H300 + H310 + H330-H373-H410
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.|1. BY MAKING PACKAGES OF DINITROBENZENE IN PAPER OR OTHER FLAMMABLE MATERIAL & BURNING IN SUITABLE COMBUSTION CHAMBER WHICH ALLOWS BURNING IN AN UNCONFINED CONDITION & IS EQUIPPED WITH APPROPRIATE EFFLUENT GAS CLEANING DEVICE. 2. BY DISSOLVING DINITROBENZENE IN FUEL OIL & ATOMIZING IN SUITABLE COMBUSTION CHAMBER EQUIPPED WITH AN APPROPRIATE EFFLUENT GAS CLEANING DEVICE.|Dissolve in combustible solvent such as alcohols, benzene, etc. Spray the solution into the furnace with afterburner and scrubber.|The following wastewater treatment technologies have been investigated for dinitrobenzene: Concentration process: Reverse osmosis. /Dinitrobenzene/
Contact with strong oxidizers may cause fires & explosions. Contact with caustics & metals such as tin & zinc may cause evolution of heat & incr in pressure.|Strong oxidizers, caustics, metals such as tin & zinc [Note: Prolonged exposure to fire and heat may result in an explosion due to spontaneous decomposition.]|Mixture with nitric acid is a high explosive.
Anon; J Appl Toxicol 9 (3): 199-202 (1989). Toxicology update for dinitrobenzene with 42 references on toxicity, metabolism, teratogenicity, mutagenicity, and carcinogenicity.
Special Hazards of Combustion Products: When heated to decomposition toxic fumes of oxides of nitrogen released. Behavior in Fire: Decomposes explosively. Can be detonated by shock or heat under confinement that will permit high pressure buildup (USCG, 1999)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.|Reactive - 4th degree
|Danger|H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]|P260, P262, P264, P270, P271, P273, P280, P284, P301+P310, P302+P350, P304+P340, P310, P314, P320, P321, P322, P330, P361, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 47 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H300: Fatal if swallowed [Danger Acute toxicity, oral]|H370: Causes damage to organs [Danger Specific target organ toxicity, single exposure]|P260, P264, P270, P273, P307+P311, P314, P321, P391, P405, and P501
Excerpt from ERG Guide 152 [Substances - Toxic (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck 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, 2016)
Excerpt from ERG Guide 152 [Substances - Toxic (Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Cover with plastic sheet to prevent spreading. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)
Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should immediately wash the skin when it becomes contaminated. Remove: Work clothing that becomes wet or significantly contaminated should be removed and replaced. Change: Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premise. Provide: Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.] (NIOSH, 2016)|Employees should be provided with and required to use impervious clothing, gloves, face shields (eight-inch minimum), and other appropriate protective clothing necessary to prevent skin contact with dinitrobenzene or liquids containing dinitrobenzene.|Respiratory protection for dinitrobenzene (all isomers): Minimum respiratory protection required above 1 mg/cu m: Particulate concentration: 5 mg/cu m or less: Any dust and mist respirator, except single-use. 10 mg/cu m or less: Any dust and mist respirator, except single-use or quarter-mask respirator, or any fume respirator or high efficiency particulate filter respirator, or any supplied-air respirator, or any self-contained breathing apparatus; 50 mg/cu m or less: A high efficiency particulate filter respirator with a full facepiece, or any supplied-air respirator with a full facepiece, helmet, or hood, or any self-contained breathing apparatus with a full facepiece; 200 mg/cu m or less: A powered air-purifying respirator with a high efficiency particulate filter, or a type C supplied-air respirator operated in pressure-demand, or other positive-pressure or continuous-flow mode; Greater than 200 mg/cu m or entry and escape from unknown concentrations: Self-contained breathing apparatus with a full facepiece operated in pressure-demand or other positive pressure mode, or a combination respirator which includes a type C supplied-air respirator with a full facepiece operated in pressure-demand or other positive pressure or continuous-flow mode and an auxiliary self-contained breathing apparatus operated in pressure-demand or other positive pressure mode. Escape: Any dust and mist respirator, except single-use, or any escape self-contained breathing apparatus.|Wear appropriate personal protective clothing to prevent skin contact.|Wear appropriate eye protection to prevent eye contact.|For more Personal Protective Equipment (PPE) (Complete) data for 1,4-DINITROBENZENE (11 total), please visit the HSDB record page.|(See protection codes)
Dinitrobenzene may detonate when subject to shock or when heated under confinement.|Impact sensitivity (minimum fall of a 2 kg weight to cause at least one explosion in ten trial(s): > 100 cm.|Mixture with nitric acid is a high explosive.
For rescue purposes wear full protective clothing. Fight fire from an explosion-resistant location. In advanced or massive fires, area should be evacuated. If fire occurs in vicinity of this material water should be used to keep containers cool. /1,2-Dinitrobenzene/|Fire Fighting Respirator: Self-contained breathing apparatus with a full facepiece operated in pressure-demand or other positive pressure mode. /Dinitrobenzene, all isomers/|If /dinitrobenzene, solid/ is on fire, or involved in fire: Use water in flooding quantities as fog, and cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible, and use alcohol foam, carbon dioxide, or dry chemical. If fire is massive, back off, protect surroundings, and let burn. /Dinitrobenzene, solid/
1. Remove all ignition sources. 2. Ventilate area of spill. 3. For small quantities, sweep onto paper or other suitable material and burn in suitable combustion chamber which allows burning in unconfined condition and is equipped with appropriate effluent gas cleaning device. Large quantities may be reclaimed; however, if this is not practical, dissolve in fuel oil and atomize in suitable combustion chamber equipped with cleaning an appropriate effluent gas cleaning device.|SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Eating and smoking should not be permitted in areas where dinitrobenzene or liquids containing dinitrobenzene are handled, processed, or stored. Employees who handle dinitrobenzene or liquids containing dinitrobenzene should wash their hands thoroughly with soap or mild detergent and water before eating, smoking, or using toilet facilities.|If employees' clothing becomes contaminated with solid dinitrobenzene, employees should change into uncontaminated clothing before leaving the work premises. ... If the clothing is to be laundered or otherwise cleaned to remove the dinitrobenzene, the person performing the operation should be informed of dinitrobenzene's hazardous properties.|Where exposure of an employee's body to liquids containing dinitrobenzene may occur, facilities for quick drenching of the body should be provided within the immediate work area for emergency use.|Good industrial hygiene practices recommend that engineering control be used to reduce environmental concentrations to the permissible exposure level. However, there are some exceptions where respirators may be used to control exposure. Respirators may be used when engineering and work practice controls are not technically feasible, when such controls are in the process of being installed, or when they fail and need to be supplemented. Respirators may also be used for operations which require entry into tanks or closed vessels, and in emergency situations. If the use of respirators is necessary, the only respirators permitted are those that have been approved by the Mine Safety and Health Administration (formerly Mining Enforcement and Safety Administration) or by the National Institute for Occupational Safety and Health.|For more Preventive Measures (Complete) data for 1,4-DINITROBENZENE (10 total), please visit the HSDB record page.
/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Health: Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. 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. /Dinitrobenzenes; Dinitrobenzenes, liquid; Dinitrobenzenes, solid/|/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. /Dinitrobenzenes; Dinitrobenzenes, liquid; Dinitrobenzenes, solid/|/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. /Dinitrobenzenes; Dinitrobenzenes, liquid; Dinitrobenzenes, solid/|/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Dinitrobenzenes; Dinitrobenzenes, liquid; Dinitrobenzenes, solid/|For more DOT Emergency Guidelines (Complete) data for 1,4-DINITROBENZENE (8 total), please visit the HSDB record page.
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.
Eyes are irritated by liquid. /1,3-Dinitrobenzene/
Permissible Exposure Limit: Table Z-1 8-hr Time-Weighted Avg: 1 mg/cu m. Skin Designation. /Dinitrobenzene (all isomers)/
Recommended Exposure Limit: 10 Hr Time-Weighted avg: 1 mg/cu m; skin.
Consult an expert! Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. Do NOT let this chemical enter the environment. Personal protection: complete protective clothing including self-contained breathing apparatus.
Separated from strong oxidants, strong bases, strong acids and food and feedstuffs. See Chemical Dangers.
No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
The substance is irritating to the eyes and respiratory tract. The substance may cause effects on the blood. This may result in the formation of methaemoglobin. The effects may be delayed. Medical observation is indicated.
The substance may have effects on the blood. This may result in anaemia. The substance may have effects on the liver. This may result in liver impairment.
NO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust.
PREVENT DISPERSION OF DUST! STRICT HYGIENE!
Use local exhaust or breathing protection.
Protective gloves. Protective clothing.
Wear face shield or eye protection in combination with breathing protection.
The major hazards encountered in the use and handling of 1,4-dinitrobenzene stem from its toxicologic properties and explosivity. Toxic by all routes (ie, inhalation, ingestion, dermal absorption), exposure to this colorless-to yellow, crystalline substance may occur from its production or use in the synthesis of dyes and as a camphor substitute in cellulose nitrate. Effects from exposure may include headache, nausea, vision impairment, contact burns to the skin and eyes, cardiac arrhythmias, methemaglobinemia, cyanosis, hepatic injury, and respiratory failure. Effects may be delayed for up to 1-4 hours. OSHA has established a time-weighted-average (TWA) exposure limit of 1 mg/cu m, with a skin designation. In activities and situations where over-exposure may occur, where a positive pressure self-contained breathing apparatus and chemical protective clothing which is specifically recommended by the shipper or manufacturer. No skin should be exposed. If contact should occur, irrigate exposed eyes with copious amounts of tepid water for at least 15 minutes, and wash exposed skin with soap and water. Contaminated clothing and sho es should be removed and left at the site for cleaning or disposal. While 1,4-dinitrobenzene does not ignite easily, it may explode by impact, contact with strong oxidizers, or heat under confinement that will permit high pressure build-up. For fires involving this substance, extinguish with dry chemical, CO2, water spray, fog, regular foam (for dinitrobenzene solution), or alcoh ol foam (for dinitrobenzene solid). Evacuate area of massive fire, and fight from as far a distance as possible. 1,4-Dinitrobenzene may be shipped via air, rail, road, and water, in containers bearing the label, "Poison." This substance should be stored away from heat, sparks, flames, and other sources of ignition,protected from physical damage, and separated from oxidizers, combustibles, metals (eg, tin and zinc), and caustics. For small dry spills of this substance, use a clean shovel to place material into a clean, dry container for later disposal (liquid solutions are taken up with sand or other noncombustible material). Large land spills (liquid solutions) should be diked far ahead of the spill for later disposal. Do not allow the material to ent er water sources or sewers. Large dry spills should be covered with a plastic sheet to prevent dissolving in the rain. For spills in water, use sand bag barriers to trap material at the bottom, apply activated carbon, and use mechanical dredges or lifts to remove immobilized masses.
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 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).
Toxicity
highly toxic
IN SUBACUTE POISONING, SYMPTOMS MAY BE PRECIPITATED BY SUNLIGHT OR BY INGESTION OF ALCOHOL. /DINITROBENZENE/
Those with blood disorders may be at increased risk.
1,4-Dinitrobenzene's production and use in the manufacture of dyes, as an organic synthesis reagent and as a camphor substitute in cellulose nitrate(1) may result in its release to the environment(SRC). 1,4-Dinitrobenzene is also an impurity in the production of 2,4,6-trinitrotoluene (TNT)(2).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 150(SRC), determined from a measured log Kow of 1.46(2) and a regression-derived equation(3), indicates that 1,4-dinitrobenzene is expected to have high mobility in soil(SRC). It has been shown that nitrophenols and nitrobenzenes adsorb strongly to clay surfaces and the mobility of 1,4-dinitrobenzene is expected to be low in soils rich in clay content(4,5). Volatilization of 1,4-dinitrobenzene from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.4X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(6). 1,4-Dinitrobenzene is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.5X10-5 mm Hg(SRC), determined from a fragment constant method(7). More than 64 days were required to biodegrade 1,4-dinitrobenzene in an aqueous biodegradation screening test using a silt loam inoculum at 25 °C(8), which suggests biodegradation will occur slowly in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 150(SRC), determined from a measured log Kow of 1.46(2) and a regression-derived equation(3), indicates that 1,4-dinitrobenzene is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected to be an important fate process(3) based upon an estimated Henry's Law constant of 8.4X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), BCF values of 2-38 measured in fish(6,7), suggests bioconcentration in aquatic organisms is low to moderate(SRC). More than 64 days were required to biodegrade 1,4-dinitrobenzene in an aqueous biodegradation screening test using a silt loam inoculum at 25 °C(8), which suggests biodegradation will also occur slowly in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,4-dinitrobenzene, which has an estimated vapor pressure of 6.5X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 1,4-dinitrobenzene 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 753 days(SRC), calculated from its rate constant of 2.1X10-14 cu cm/molecule-sec at 25 °C (SRC) determined using a structure estimation method(3). 1,4-Dinitrobenzene absorbs light greater than 290 nm and may be susceptible to direct photolysis(4), but the kinetics of this reaction are unknown(SRC). Particulate-phase 1,4-dinitrobenzene may be removed from the air by wet and dry deposition(SRC).
The rate constant for the vapor-phase reaction of 1,4-dinitrobenzene with photochemically-produced hydroxyl radicals has been estimated as 2.1X10-14 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 753 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Nitrobenzenes absorb light greater than 290 nm(2), which suggests that 1,4-dinitrobenzene may be susceptible to direct photolysis in the environment(SRC). Hydrolysis is not expected to be an important fate process for 1,4-dinitrobenzene since this compound lacks functional groups that undergo hydrolysis under environmental conditions(2).
A BCF value of 5 was measured for 1,4-dinitrobenzene in fish(1). BCF values of 2-38 were measured in carp exposed to dinitrobenzene (isomer not specified) over a 6 week incubation period(2). According to a classification scheme(3), this BCF value suggest bioconcentration in aquatic organisms is low to moderate(SRC).
The Koc of 1,4-dinitrobenzene is estimated as 150(SRC), using a measured log Kow of 1.46(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 1,4-dinitrobenzene is expected to have high mobility in soil. It has been shown that nitrophenols and nitrobenzenes adsorb strongly to clay through an interaction between the nitro group and the water molecules or metallic cations in the clay(4), and 1,4-dinitrobenzene is expected to similarly bind to clays(SRC). The adsorption of 1,4-dinitrobenzene was studied in monmorillonite, kaolinite and illite clays(5). Adsorption coefficients (Kd) of 188, 1,460 and 3,100 L/kg were measured in kaolinite, illite and monmorillonite, respectively(5).
The Henry's Law constant for 1,4-dinitrobenzene is estimated as 8.4X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 1,4-dinitrobenzene is expected to be essentially nonvolatile from water(2). 1,4-Dinitrobenzene's Henry's Law constant(1) indicates that volatilization from moist soil surfaces is not expected to occur(SRC). 1,4-Dinitrobenzene is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.5X10-4 mm Hg(SRC), determined from a fragment constant method(3).
Occupational exposure to 1,4-dinitrobenzene may occur through inhalation and dermal contact with this compound at workplaces where 1,4-dinitrobenzene is produced or used. (SRC)
Drug Information
It is readily absorbed through the skin, either as solid, liquid, or vapor.
The redn of aromatic nitro cmpds was investigated in a purified milk xanthine oxidase system. Para substituted nitro cmpds with electron-withdrawing groups served as efficient electron acceptors, whereas those with electron-repelling groups were less active. The redn rate was greatest for p-substitution of electron-withdrawing groups, and for m-substitution of electron-repelling groups, respectively.|Nitroreductase activity was previously known to occur under nitrogen atmosphere in the cytosolic and microsomal fractions of liver homogenates. This study describes a subcellular nitroreductase activity which occurs in liver mitochondria under aerobic conditions. Mitochondria were isolated from rat liver and assayed for their capacity to reduce certain nitro compounds by measuring spectrophotometrically both the appearance of amino compounds and the consumption of nicotinamide adenine dinucleotide. Intact mitochondria were found to possess a p-dinitrobenzene reductase activity. The activity was destroyed by heat, and was present at only 20% in the microsomal fraction. It was strictly nicotinamide adenine dinucleotide-dependent, while only little or no activity occurred with reduced nicotinamide adenine dinucleotide or other oxidative substrates. Nitro reduction was inhibited by thiol reagent. Rat liver mitochondria showed about 15% activity with o-dinitrobenzene and m-dinitrobenzene, while there was less than 5% activity with a series of p-nitro compounds including chloramphenicol.|The metabolism of radiolabeled dinitrobenzene isomers was compared in hepatocytes and hepatic subcellular fractions isolated from male Fischer-344 rats. Under aerobic conditions, reduction was the major metabolic pathway for m- and p-dinitrobenzene in hepatocytes with m- and p-nitroaniline accounting for 74.0 + or - 1.2 and 81.0 + or - 0.6% (mean + or - standard error, n= 4), respectively, of the radioactivity present after a 30 min incubation. The major metabolite of o-dinitrobenzene in similar incubations was S-(2-nitrophenyl)glutathione which represented 48.1 + or - 5.5% of the total radioactivity; o-nitroaniline accounted for 29.5 + or - 2.1% of the radioactivity. Incubation of dinitrobenzene with microsomes produced nitroanilines as well as nitrosonitrobenzenes and nitrophenylhydroxylamines. Reduction of o- and m-dinitrobenzene by microsomes was reduced nicotinamide adenine dinucleotide dependent. Reduction of p-dinitrobenzene could be supported by nicotinamide adenine dinucleotide as well as reduced nicotinamide adenine dinucleotide, although the rate of reduction was slower with nicotinamide adenine dinucleotide. Conjugation of o- and p-dinitrobenzene, but not m-dinitrobenzene with glutathione occurred in cytosol incubations although only o-dinitrobenzene formed the glutathione conjugate in intact hepatocytes.
INHALATION OR INGESTION: Headache, vertigo, nausea, vomiting, diarrhea, fever, rapid weak pulse, decreased blood pressure, cyanosis, exhaustion, hepatomegaly, jaundice, albuminurea, hematuria, visual scotomata, amblyopia and nystagmus. EYES: Irritation. SKIN: Stains skin yellow; if skin contact is prolonged, can be absorbed into blood causing same symptoms as for inhalation. (USCG, 1999)
Eye: If this chemical contacts the eyes, immediately wash the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately. Contact lenses should not be worn when working with this chemical. Skin: If this chemical contacts the skin, immediately wash the contaminated skin with soap and water. If this chemical penetrates the clothing, immediately remove the clothing, wash the skin with soap and water, and get medical attention promptly. Breathing: If a person breathes large amounts of this chemical, move the exposed person to fresh air at once. If breathing has stopped, perform mouth-to-mouth resuscitation. Keep the affected person warm and at rest. Get medical attention as soon as possible. Swallow: If this chemical has been swallowed, get medical attention immediately. (NIOSH, 2016)|(See procedures)
Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.
Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Basic treatment: Establish a patent airway. 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 ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline 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 patent can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aniline and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aniline and related compounds/
IN CASES OF CHRONIC POISONING, IMPAIRMENT OF VISION APPEARS TO HAVE BEEN COMMON. ... VISUAL FIELDS ... SLIGHTLY CONTRACTED, & VISUAL ACUITY ... REDUCED, WITH CENTRAL SCOTOMAS, PARTICULARLY FOR RED & GREEN. USUALLY THERE HAS BEEN NO ABNORMALITY IN APPEARANCE OF THE OPTIC NERVEHEAD OTHER THAN SLIGHT PALLOR ... PARTIAL OPTIC ATROPHY ... VISION HAS GRADUALLY RECOVERED. /DINITROBENZENE/|SURFACE CONTACT MAY CAUSE YELLOWING OF SKIN, & PURPORTEDLY OF CONJUNCTIVA & CORNEA ... SKIN, CONJUNCTIVA, & OCULAR FUNDUS MAY SHOW BLUISH DISCOLORATION ... /DINITROBENZENE/|CHRONIC POISONING ... FOLLOWING EXPOSURE FOR 9 TO 18 MO TO DUST & VAPOR IN MUNITIONS PLANTS. SYMPTOMS ... START WITH HEADACHE, & BURNING PAIN & PARESTHESIA IN FEET, ANKLES, HANDS, & FOREARMS. ... APATHY & TIREDNESS, SHORTNESS OF BREATH & PALPITATION OF HEART. PERIPHERAL NERVE DISTURBANCES HAVE ALL BEEN SENSORY ... VISION HAS BEEN AFFECTED ... . /DINITROBENZENE/|NITRO CMPD OF DINITROBENZENE ... TYPE HAVE HISTORY OF PROMINENT HEPATOTOXIC EFFECTS ... HEPATIC INJURY IS MANIFESTED BY JAUNDICE ... DEMONSTRABLE IN CONJUNCTIVAE ... POTENT METHEMOGLOBIN PRODUCER ... CYANOSIS PROVIDES WARNING OF EXPOSURE ... /DINITROBENZENE/|For more Human Toxicity Excerpts (Complete) data for 1,4-DINITROBENZENE (6 total), please visit the HSDB record page.
1,4-dinitrobenzene
The substance can be absorbed into the body by inhalation, through the skin and by ingestion.|inhalation, skin absorption, ingestion, skin and/or eye contact
Anoxia, cyanosis; visual disturbance, central scotomas; bad taste, burning mouth, dry throat, thirst; yellowing hair, eyes, skin; anemia; liver damage
Burning sensation. Blue lips, fingernails and skin. Dizziness. Headache. Laboured breathing. Nausea. Weakness.
MAY BE ABSORBED! See Inhalation.
Redness. Pain.
Eyes, skin, blood, liver, cardiovascular system, central nervous system
1,4-Dinitrobenzene Use and Manufacturing
Prepared by p-nitroaniline through the following steps. Dissolve p-nitroaniline in fluoroboric acid solution and cool with an ice bath. Aqueous sodium nitrite solution was added dropwise with stirring. After the addition, it was stirred for a few minutes and filtered with suction. The obtained diazonium fluoroborate was washed with cold fluoroboric acid, 95% ethanol, and ether, and then made into a suspension with water. The suspension was slowly added to the mixture of aqueous sodium nitrite and copper powder with stirring. After the addition is completed, it is filtered, and the crystals are washed with water, dilute sodium hydroxide solution and water. Dry at 110°C. After grinding into powder, extract it with benzene, distill the extract, and the residue after recovering benzene is crystallized with glacial acetic acid to obtain p-dinitrobenzene. The yield is 67-82%.
manufacture of dyes, dye intermediates, explosives, plastics.
GRADE: TECHNICAL.
Benzene, 1,4-dinitro-: ACTIVE
Hazardous organic and inorganic cmpd, incl p-dinitrobenzene, in water were determined by gas chromatography and mass spectroscopy.|The use of a commercial thermionic detector that has been tuned to give a high detection sensitivity towards organosulfur is reported. Compounds tested include ... p-dinitrobenzene.|OSW Method 8091. Nitroaromatics and Cyclic Ketones: Capillary Column Technique.|OSW Method 8270B. Determination Semivolatile Organic compounds by Gas Chromatography/Mass Spectrometry (GC/MS): Capillary Column Technique. Detection limit = 40.0 ug/l.|EAD Method 1625. Semivolatile Organic Compounds by Isotope Dilution GCMS. Detection limit = 10.0 ug/l.
Fire Hazards -> Reactive - 4th degree
Computed Properties
Molecular Weight:168.11
XLogP3:1.5
Hydrogen Bond Acceptor Count:4
Exact Mass:168.01710661
Monoisotopic Mass:168.01710661
Topological Polar Surface Area:91.6
Heavy Atom Count:12
Complexity:165
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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