1,3-Dinitrobenzene
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1,3-Dinitrobenzene
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CAS No:
99-65-0
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Formula:
C6H4N2O4
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Chemical Name:
1,3-Dinitrobenzene
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Synonyms:
Benzene,1,3-dinitro-;Benzene,m-dinitro-;1,3-Dinitrobenzene;m-Dinitrobenzene;DNB;Meta-dinitrobenzene;m-Dinitrobenzene;NSC 7189;DNB (explosive)
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CAS No:
Description
orange to yellow crystalline powder
M-dinitrobenzene is a yellow solid with a slight odor. Sinks in water. (USCG, 1999)|YELLOW CRYSTALS.|Pale-white or yellow solid.
M-dinitrobenzene is a yellow solid with a slight odor. Sinks in water. (USCG, 1999)|1,3-dinitrobenzene is a dinitrobenzene that is benzene disubstituted at positions 1 and 3 with nitro groups. It has a role as a neurotoxin.
1,3-Dinitrobenzene Basic Attributes
168.11
168.11
1105654
202-776-8
DK8B627BU0
0691
7189
1597|3443
DTXSID9024065
Yellowish crystals|Colorless to yellow, rhombic needles or plates|Pale white or yellow, crystalline solid.
2904209090
Characteristics
91.6
1.49
M-dinitrobenzene is a yellow solid with a slight odor. Sinks in water. (USCG, 1999)
1.575 g/cm3 @ Temp: 18 °C
89-90 °C
302.8 °C @ Press: 770 Torr
150 °C
1.612
H2O: 500 mg/L (20 ºC)
2-8°C
Vapour pressure, kPa at 20°C:
Relative vapour density (air = 1): 5.8
Oral-Rat LD50: 59.5 mg/kg; Oral-Mouse LD50: 74.7 mg/kg
Inflammable in case of open flame, high temperature, oxidant; burning produces toxic nitrogen oxide fumes
Strong oxidizers, caustics, metals such as tin & zinc. [Note: Prolonged exposure to fire and heat may result in explosion due to spontaneous decomposition.]
4.90e-08 atm-m3/mole|Henry's Law constant = 4.9X10-8 atm-cu m/mole @ 25 °C
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].
-696.8 kcal @ 20 °C (solid)
10.43 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
26/27/28-33-50/53-40-36/37/38-23/24/25-11-52/53-36-20/21/22
28-36/37-45-60-61-28A-27-16-26
CZ7350000
T+,N,T,F,Xn
Treasury is ventilated, low temperature and dry; stored separately from oxidant
Explosive when mixed with oxidant
Stable. Incompatible with reducing agents, oxidizing agents, strong bases. May explode if heated.
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 a suitable combustion chamber which allows burning in an unconfined condition & is equipped with an appropriate effluent gas cleaning device. 2. By dissolving dinitrobenzene in fuel oil & atomizing in a 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/
Mixture with nitric acid is a high explosive. Mixture with tetranitromethane is a high explosive very sensitive to sparks.|Contact with strong oxidizers may cause fires and explosions. Contact with caustics and metals such as tin and zinc may cause evolution of heat and increase in pressure.
Dangerous Prop Ind Mater Rep 6 (1): 49-52 (1986). Review dinitrobenzene safety toxicol; Health hazard of dinitrobenzene.|Anonymous; J Appl Toxicol 9 (3): 199-202 (1989). Toxicology update for dinitrobenzene with 42 references on toxicity, metabolism, teratogenicity, mutagenicity, and carcinogenicity.|U.S. Dept Health & Human Services/Agency for Toxic Substances Disease Registry; Toxicological Profile for 1,3-Dinitrobenzene/1,3,5-Trinitrobenzene (1995) NTIS # PB/95/264289/AS|DHHS/ATSDR; Toxicological Profile for 1,3-Dinitrobenzene and 1,3,5-Trinitrobenzene (June 1995)
Behavior in Fire: May explode (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 139 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]|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P272, P280, P281, P301+P310, P302+P352, P305+P351+P338, P307+P311, P308+P313, P312, P314, P321, P322, P330, P333+P313, P337+P313, P363, P405, and P501|P201, P202, P260, P261, P264, P270, P272, P273, P280, P281, P301+P310, P302+P352, P305+P351+P338, P307+P311, P308+P313, P312, P314, P321, P322, P330, P333+P313, P337+P313, P363, 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)
SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material under freezer conditions. (NTP, 1992)
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. /SRP: Liquid dinitrobenzene will attack some forms of plastics, rubber, and coatings./|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 1,3-DINITROBENZENE (12 total), please visit the HSDB record page.|(See protection codes)
Combustible
SEVERE EXPLOSION HAZARD WHEN EXPOSED TO SHOCK OR FLAME|Impact sensitivity (minimum fall of a 2 kg weight to cause at least one explosion in ten trial(s): > 100 cm.|Strong oxidizers, caustics, metals such as tin & zinc. [Note: Prolonged exposure to fire and heat may result in explosion due to spontaneous decomposition.]
Fire Fighting Respirator: Self-contained breathing apparatus with a full facepiece operated in pressure-demand or other positive pressure mode.
1. Remove all ignition sources. 2. Ventilate area of spill. 3. For small quantities, sweep onto paper or other suitable material & burn in a suitable combustion chamber which allows burning in an unconfined condition & is equipped with an appropriate effluent gas cleaning device. Large quantities may be reclaimed; however, if this is not practical, dissolve in fuel oil & atomize in a suitable combustion chamber equipped with an appropriate effluent gas cleaning device.
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.|Protect containers against physical damage. Keep away from heat and sources of ignition or acute fire hazard area. Storage area should be equipped with an automatic sprinkler system if within a building.|Clothing contaminated with dinitrobenzene should be placed in closed containers for storage until it can be discarded or until provision is made for the removal of dinitrobenzene from the clothing.|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.|For more Preventive Measures (Complete) data for 1,3-DINITROBENZENE (12 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 1,3-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.
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 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. The substance may have effects on the nervous system. Animal tests show that this substance possibly causes toxicity to human reproduction or development. May cause impaired vision.
NO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust.
PREVENT DISPERSION OF DUST! STRICT HYGIENE! IN ALL CASES CONSULT A DOCTOR!
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 1,3-dinitrobenzene stem from its toxicologic properties and explosivity. Toxic by all routes (ie, inhalation, ingestion, dermal absorption), exposure to this yellowish, crystalline substance may occur from its use in the production of analine, dyes, explosives, industrial solvents, and pesticides. Effects from exposure mayinclude contact burns to the skin and eyes, headache, nausea, lethargy, heart palpitations, methemoglobinemia, jaundice, and respiratory failure. Effects may be delayed up to 1-4 hours. OSHA has established an 8 hour, Time Weighted Average (TWA) limit of 1 mg/cu m, with a skin designation for this substance. In activities and situations where over-exposure may occur, wear a positive pressure self-contained breathing apparatus and chemical protective clothing which is specifically recommended by the shipper or manufacturer. If contact should occur, irrigate exposed eyes with copious amounts of tepid water for at least 15 minutes and wash exposed skin thoroughly with soap and water. Contaminated clothing should be removed and discarded or left at the site for cleaning before being reworn. 1,3-Dinitrobenzene is a severe explosion hazard when exposed to friction, mechanical shock, localized thermal shock, or contamination. For fires involving 1,3-dinitrobenzene, extinguish with dry chemical, CO2, water spray, fog, or standard foam. Fight the fire from as far a distance as possible in an explosion-resistant location. If fire is massive, back off, protect surroundings, and let burn. 1,3-Dinitrobenzene may be transported via air, rail, road, and water, in containers bearing the label, "Poison." 1,3-Dinitrobenzene should be stored in a permanent magazine, away from heat, sources of ignition, sources of physical damage, oxidizers, combustibles, caustics, and metals such as tin and zinc. For small spills of 1,3-dinitrobenzene, use a clean shovel to place material into clean, dry, covered containers for later disposal (liquid solutions are taken up with sand or other noncombustible absorbent). Dike far ahead of large liquid spills to prevent runoff. Large dry spills should be covered with plastic sheeting. Large spills into bodies of water should be trapped at the bottom with sand bag barriers, 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).
The concentration of 1,3-dinitrobenzene in an extract of effluent water from organics and plastics industries was 1,055 ng/ul(1). 1,3-Dinitrobenzene has been detected in the effluent of facilities that produce 2,4,6-trinitrotoluene (TNT) at a concn of 4 ppm(2).
Toxicity
highly toxic
IN SUBACUTE POISONING, SYMPTOMS MAY BE PRECIPITATED BY SUNLIGHT OR BY INGESTION OF ALCOHOL. /DINITROBENZENE/
LD50 Rat oral as a 1% suspension in corn oil 83 mg/kg with fiducial limits 56-124 mg/kg|LD50 Rat ip 28 mg/kg|LD50 Dog iv 10 mg/kg|LD50 Wild bird oral 42 mg/kg|For more Non-Human Toxicity Values (Complete) data for 1,3-DINITROBENZENE (8 total), please visit the HSDB record page.
Those with blood disorders may be at increased risk.
1,3-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). 1,3-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 1.49(2) and a regression-derived equation(3), indicates that 1,3-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 1,3-dinitrobenzene is expected to be low in soils rich in clay content(4,5). Volatilization of 1,3-dinitrobenzene from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 4.9X10-8 atm-cu m/mole(6). 1,3-Dinitrobenzene is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2X10-4 mm Hg(6). More than 64 days were required to biodegrade 1,3-dinitrobenzene in an aqueous biodegradation screening test using a silt loam inoculum at 25 °C(7), 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 1.49(2) and a regression-derived equation(3), indicates that 1,3-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 a Henry's Law constant of 4.9X10-8 atm-cu m/mole(4). According to a classification scheme(5), BCF values of 2-75 measured in fish(6,7), suggests bioconcentration in aquatic organisms is low to moderate (SRC). The half-life of 1,3-dinitrobenzene in water from the Tennessee River, 1 mile downstream from a munitions plant, was 1 day(8). However, 1,3-dinitrobenzene did not biodegrade in pristine water from rivers and creeks in Maryland(8), suggesting that biodegradation may occur rapidly in acclimated environments, but slowly under non-acclimated conditions(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,3-dinitrobenzene, which has a vapor pressure of 2X10-4 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist in the vapor phase in the ambient atmosphere. Vapor-phase 1,3-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 526 days(SRC), calculated from its rate constant of 3X10-14 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). 1,3-Dinitrobenzene absorbs light greater than 290 nm and may be susceptible to direct photolysis(4), but the kinetics of this reaction are unknown(SRC).
The rate constant for the vapor-phase reaction of 1,3-dinitrobenzene with photochemically-produced hydroxyl radicals has been estimated as 3X10-14 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 526 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 1,3-dinitrobenzene may be susceptible to direct photolysis in the environment(SRC). Hydrolysis is not expected to be an important fate process for 1,3-dinitrobenzene since this compound lacks functional groups that undergo hydrolysis under environmental conditions(2).
5.89|A BCF value of 75 was measured for 1,3-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 1,3-dinitrobenzene is estimated as 150(SRC), using a measured log Kow of 1.49(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 1,3-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 1,3-dinitrobenzene is expected to similarly bind to clays(SRC). The adsorption of 1,3-dinitrobenzene was studied in montmorillonite, clay and an adsorption coefficient of 4,500 L/kg was measured(5).
The Koc of 1,3-dinitrobenzene is estimated as 150(SRC), using a measured log Kow of 1.49(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 1,3-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 1,3-dinitrobenzene is expected to similarly bind to clays(SRC). The adsorption of 1,3-dinitrobenzene was studied in monmorillonite clay and an adsorption coefficient of 4,500 L/kg was measured(5).
Occupational exposure to 1,3-dinitrobenzene may occur through inhalation and dermal contact with this compound at workplaces where 1,3-dinitrobenzene is produced or used. (SRC)
Drug Information
It is readily absorbed through the skin, either as solid, liquid or vapor.|Male F-344 rats were given a single oral or ip dose of 20 or 25 mg/kg of 1,3-dinitrobenzene or split ip doses of two 10 mg treatments (separated by a four hr interval) daily. Rats were divided into the following groups of six individuals each: conventional, germ-free, & germ-free repopulated with suspensions of bacteria. After an oral dose of 25 mg/kg, the formation of methemoglobin with time was similar for conventional & germ-free rats. ... When administered (14)C-labeled 1,3-dinitrobenzene, whole blood, plasma, liver, kidney, testis, sciatic nerve, white & brown fat, & brain stem of germ-free rats had higher concns of radioactivity than the respective tissues of conventional rats. Following admin of a single oral dose of 25 mg/kg, whole blood of conventional rats had a peak mean concn of the parent cmpd of 4.2 ug/ml at 0.5 hr. Half-life was approx 10 hr. In germ-free rats the peak concn was 7.5 ug/ml after 0.5 hr (maintained for 6 hr); half-life was 20 hr. ...|In, animals, 1,3-DNB is rapidly absorbed by the oral route; data from one study indicate that at least 70% of a single oral dose was absorbed. In animals, depending on the vehicle, 1,3-DNB can also be readily absorbed through the skin. It appears that polar vehicles facilitate absorption. ... Following oral exposure, the main route of excretion of 1,3-DNB metabolites in animals is the urine.|Rabbits treated with randomly labeled 14-C-1,3-DNB in arachis oil in single doses of 50-100 mg/kg excreted 65-93% of the administered radioactivity in the urine within 2 days of dosing. This indicated that at least that amount was absorbed from the GI tract. Similar results were reported in rats in which excretion data suggested that at least 63% of a single oral dose was absorbed.
... METABOLIZED ... BY REDN OF 1 OR BOTH NITRO GROUPS, & BY HYDROXYLATION OF BENZENE RING, TO PRODUCE DINITRO-, AMINONITRO-, & DIAMINOPHENOLS. AFTER FEEDING M-DINITROBENZENE (LABELLED WITH (14)CARBON) TO RABBITS THE METABOLITES PRESENT IN THE URINE WERE M-NITROANILINE ... M-PHENYLENEDIAMINE ... 2-AMINO-4-NITROPHENOL ... 4-AMINO-2-NITROPHENOL & 2,4-DIAMINOPHENOL. ... THE ABSENCE OF ANY 3,5-SUBSTITUTED PHENOLS SUGGESTS THAT REDN OF 1 OF NITRO GROUPS PRECEDES HYDROXYLATION.|The biotransformation of m-dinitrobenzene was studied in rabbits. The animals recieved a single oral dose of radiocarbon-labeled m-DNB in the range of 50 to 100 mg/kg. Urine was collected for two days after dosing for analysis of metabolites. Over the two day period, more than 80% of the radiolabel was excreted in the urine; feces contained between 0.3 and 5.2% of the radioactive dose. m-DNB underwent extensive biotransformation. The major urinary metabolites were 2,4-diaminophenol (31% of the dose), m-nitroaniline and m-phenylenediamine (together, 35% of the dose), and 2-amino-4-nitrophenol (24%).|The redn of aromatic nitro compounds was investigated in purified milk xanthine oxidase system. ... 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 reagents. 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 dinitrobenzenes 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.
Following admin of a single oral dose of 25 mg/kg, whole blood of conventional rats had a peak mean concn of the parent cmpd of 4.2 ug/ml at 0.5 hr. Half-life was approx 10 hr. In germ-free rats the peak concn was 7.5 ug/ml after 0.5 hr (maintained for 6 hr); half-life was 20 hr. ...
Inhalation or ingestion causes loss of color, nausea, headache, dizziness, drowsiness, and collapse. Eyes are irritated by liquid. Stains skin yellow; if contact is prolonged, can be absorbed into blood and cause same symptoms as for inhalation. (USCG, 1999)
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Generally, the induction of vomiting is NOT recommended outside of a physician's care due to the risk of aspirating the chemical into the victim's lungs. However, if the victim is conscious and not convulsing and if medical help is not readily available, consider the risk of inducing vomiting because of the high toxicity of the chemical ingested. Ipecac syrup or salt water may be used in such an emergency. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)|(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 1,3-DINITROBENZENE (14 total), please visit the HSDB record page.
1,3-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. Nausea. Weakness. Laboured breathing.
MAY BE ABSORBED! See Inhalation.
Redness. Pain.
Eyes, skin, blood, liver, cardiovascular system, central nervous system
1,3-Dinitrobenzene Use and Manufacturing
It is obtained by nitration of nitrobenzene by mixed acid. The crude dinitrobenzene is refined with sodium sulfite solution. The refined filtrate mainly contains sodium nitrobenzene sulfonate, which is the reaction product of o-dinitrobenzene and p-dinitrobenzene with sodium sulfite. When nitrobenzene is nitrated with mixed acid, the intermediate dinitrobenzene accounts for 88%, o-dinitrobenzene 10%, and p-dinitrobenzene 2%. The separation method of isomers also has a post-treatment process designed using the different solubility of the three to ethanol or benzene.
Mainly used in the manufacture of m-phenylenediamine, m-dichlorobenzene and other dyes, pesticides and pharmaceutical intermediates
(1975) PROBABLY GREATER THAN 4.54X10+5 G|(1977) PROBABLY GREATER THAN 2.27X10+6 G
Benzene, 1,3-dinitro-: ACTIVE|OF 3 ISOMERS OF DINITROBENZENE, META-DINITROBENZENE IS MOST COMMONLY MANUFACTURED.|Selective control of weeds.
A simple procedure has been developed for the determination of munitions present in water at levels as low as 0.1 ug/liter. The method uses 60-80 mesh XAD-4 for extraction, followed by elution with 20 ml of ethyl acetate, concentration of the eluate, separation by capillary gas chromatography, and detection using electron capture.|EPA Method 8090. Gas Chromatographic Method for the detection of ppb levels of nitroaromatic and cyclic ketone compounds. Detection is achieved by an electron capture detector (ECD) for dinitrotoluenes or a flame ionization detector (FID) for the other compounds amenable to this method. The method detection limit of dinitrobenzene is not given. Precision and method accuracy were found to be directly related to the concentration of the analyte and essentially independent of the sample matrix. /Dinitrobenzene/|EAD Method 1625. Semivolatile Organic Compounds by Isotope Dilution GCMS. Detection limit = 10.0 ug/l.|OSW Method 8270B. Determination Semivolatile Organic compounds by Gas Chromatography/Mass Spectrometry (GC/MS): Capillary Column Technique. Detection limit = 20.0 ug/l.|For more Analytic Laboratory Methods (Complete) data for 1,3-DINITROBENZENE (6 total), please visit the HSDB record page.
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:175
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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