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Home > Encyclopedia > 1,2-Dinitrobenzene

1,2-Dinitrobenzene

1,2-Dinitrobenzene structure

1,2-Dinitrobenzene 

structure
  • CAS No:

    528-29-0

  • Formula:

    C6H4N2O4

  • Chemical Name:

    1,2-Dinitrobenzene

  • Synonyms:

    Benzene,1,2-dinitro-;Benzene,o-dinitro-;1,2-Dinitrobenzene;o-Dinitrobenzene;Ortho-dinitrobenzene;NSC 60682

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

light yellow-brown powder


O-dinitrobenzene is a colorless to yellow solid. Sinks and slowly mixes with water. (USCG, 1999)|WHITE-TO-YELLOW CRYSTALS.|Pale-white or yellow solid.


O-dinitrobenzene is a colorless to yellow solid. Sinks and slowly mixes with water. (USCG, 1999)|1,2-dinitrobenzene is a dinitrobenzene.

1,2-Dinitrobenzene Basic Attributes

168.11

168.11

208-431-8

35XUO924Y0

0460

60682

3443|1597

DTXSID4024066

COLORLESS OR YELLOW CRYSTALS, NEEDLES OR PLATES|White to yellow monoclinic plates|White crystals|Pale white or yellow, crystalline solid.

29042000

Characteristics

91.6

1.69

O-dinitrobenzene is a colorless to yellow solid. Sinks and slowly mixes with water. (USCG, 1999)

1.3119 g/cm3

117-118.5 °C

319 °C @ Press: 773 Torr

150 °C

1.612

H2O: 150 mg/L (20 ºC);chloroform: soluble 5%, clear, yellow-green

STORE ONLY IN PERMANENT MAGAZINE. THIS HIGH EXPLOSIVE SHOULD BE KEPT WELL AWAY FROM INITIATOR EXPLOSIVES; PROTECTED FROM PHYSICAL DAMAGE; SEPARATED FROM OXIDIZING MATERIALS, COMBUSTIBLES, & SOURCES OF HEAT.

Vapour pressure, kPa at 20°C:

Relative vapour density (air = 1): 5.8

Oral-Cat LD50: 29 mg/kg

Inflammable in case of open flame, high temperature, oxidant; burning produces toxic nitrogen oxide fumes

Mixtures with nitric acid are highly explosive.

1 mg/cu m= 0.14 ppm, 1 ppm= 6.99 mg/cu m

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].

10.71 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(a)

UN 3443 6.1/PG 2

3

26/27/28-33-50/53

28-36/37-45-60-61-28A

CZ7450000

T+,N

Treasury is ventilated, low temperature and dry; stored separately from oxidant

Explosive when mixed with oxidant

Highly reactive.

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 and burning in suitable combustion chamber which allows burning in an unconfined condition and is equipped with appropriate effluent gas cleaning device. 2. By dissolving dinitrobenzene in fuel oil and 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.|Mixtures with nitric acid are highly explosive.|Strong oxidizers, caustics, metals such as tin & zinc [Note: Prolonged exposure to fire & heat may result in spontaneous decomposition.]

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.

Special Hazards of Combustion Products: Emits highly toxic fumes of oxides of nitrogen. May explode. Behavior in Fire: Severe explosion hazard when exposed to heat or flame, or when shocked. (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: 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|H316: Causes mild skin irritation [Warning Skin corrosion/irritation]|P260, P261, P264, P270, P271, P280, P304+P340, P305+P351+P338, P307+P311, P312, P314, P321, P332+P313, P337+P313, P403+P233, P405, and P501|Warning|H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]|P273, P391, and P501|H370: Causes damage to organs [Danger Specific target organ toxicity, single exposure]|P260, P264, P270, P273, P307+P311, P314, P321, P391, P405, and P501

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 1,2-DINITROBENZENE (11 total), please visit the HSDB record page.|(See protection codes)

Combustible when exposed to heat or flame; can react vigorously with oxidizing materials.

Severe explosion hazard. Although somewhat less sensitive to shock than trinitrotoluene, it can be detonated by shock or heat under confinement that will permit high pressure build-up.|Impact sensitivity: minimum fall of a 2 kg weight to cause at least one explosion in ten trial(s): > 100 cm. /Dinitrobenzene, all isomers/|When heated to decomposition it ... explodes.|Mixtures with nitric acid are highly 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.|Fire Fighting Respirator: Self-contained breathing apparatus with a full facepiece operated in pressure-demand or other positive pressure mode. /Dinitrobenzene, all isomers/

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 & 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 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.|If employees' clothing may have become 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.|Non-impervious clothing which becomes contaminated with liquids containing dinitrobenzene should be removed immediately and non-impervious clothing which becomes contaiminated with dinitrobenzene should be removed promptly and such clothing should not be reworn until the dinitrobenzene is removed from the clothing. 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.|For more Preventive Measures (Complete) data for 1,2-DINITROBENZENE (13 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 1,2-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! Personal protection: complete protective clothing including self-contained breathing apparatus. Do NOT let this chemical enter the environment. 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.

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 liver. This may result in liver impairment. The substance may have effects on the blood. This may result in anaemia.

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.

| 3 - Materials that, under emergency conditions, can cause serious or permanent injury.| 1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.| 4 - Materials that in themselves are readily capable of detonation or explosive decomposition or explosive reaction at normal temperatures and pressures.

The major hazards encountered in the use and handling of 1,2-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 explosives, and as a camphor substitute in cellulose nitrat e production. Effects from exposure may include headache, nausea, vision impairment, contact burns to the skin and eyes, cardiac arrhythmias, methemoglobinemia, cyanosis, and hepatic injury. Effects may be delayed for several hours and may be precipitated by exposure to sunlight or ingestion of alcohol. 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, wear 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 thoroughly with soap and water. Contamin ated clothing and shoes should be removed and left at the site for cleaning or disposal. While 1,2-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 dinitrobenzen e solution), or alcohol foam (for dinitrobenzene solid). Evacuate area of massive fire, and fight from as far a distance as possible. 1,2-Dinitrobenzene may 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 separatedfrom oxidizers, combustibles, metals (eg, tin and zinc), nitric acid, 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 enter 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. /Dinitrobenzene/

1,2-Dinitrobenzene's production and use in the manufacture of dyes and explosives, as an organic synthesis reagent and as a camphor substitute in cellulose nitrate(1) may result in its release to the environment(SRC). 1,2-Dinitrobenzene is also an impurity produced during the production of 2,4,6-trinitrotoluene (TNT)(2).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 200(SRC), determined from a measured log Kow of 1.69(2) and a regression-derived equation(3), indicates that 1,2-dinitrobenzene is expected to have moderate mobility in soil(SRC). It has been shown that nitrophenols and nitrobenzenes adsorb strongly to clay surfaces and the mobility of 1,2-dinitrobenzene is expected to be low in soils rich in clay content(4,5). Volatilization of 1,2-dinitrobenzene from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.3X10-8 atm-cu m/mole(SRC), calculated from a vapor pressure of 4.5X10-5 mm Hg(6) and water solubility of 133 mg/l(7). 1,2-Dinitrobenzene is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(6). More than 64 days were required to biodegrade 1,2-dinitrobenzene in silt loam 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 200(SRC), determined from a measured log Kow of 1.69(2) and a regression-derived equation(3), indicates that 1,2-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 5.3X10-8 atm-cu m/mole(SRC), calculated from a vapor pressure of 4.5X10-5 mm Hg(4) and water solubility of 133 mg/l(5). According to a classification scheme(6), BCF values of 2-38 measured in fish(7,8), suggests bioconcentration in aquatic organisms is low to moderate (SRC). More than 64 days were required to biodegrade 1,2-dinitrobenzene in an aqueous biodegradation screening test using a silt loam inoculum at 25 °C(9), 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), 1,2-dinitrobenzene, which has a vapor pressure of 4.5X10-5 mm Hg at 25 °C(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 1,2-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). 1,2-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 1,2-dinitrobenzene may be removed from the air by wet and dry deposition(SRC).

The rate constant for the vapor-phase reaction of 1,2-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 1,2-dinitrobenzene may be susceptible to direct photolysis in the environment(SRC). Hydrolysis is not expected to be an important fate process for 1,2-dinitrobenzene since this compound lacks functional groups that undergo hydrolysis under environmental conditions(2).

A BCF value of 10 was measured for 1,2-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), these BCF values suggest bioconcentration in aquatic organisms is low to moderate(SRC).

The Koc of 1,2-dinitrobenzene is estimated as 200(SRC), using a measured log Kow of 1.69(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 1,2-dinitrobenzene is expected to have moderate 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). However, it has also been shown that ortho substituents on the benzene ring, as in the case of 1,2-dinitrobenzene, diminish this adsorption due to steric effects(5). The adsorption of 1,4-dinitrobenzene and 1,2-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 for 1,4-dinitrobenzene, while the adsorption coefficients were only 0.4, 2.5 and 4.2 L/kg for 1,2-dinitrobenzene(5).

The Henry's Law constant for 1,2-dinitrobenzene is estimated as 5.3X10-8 atm-cu m/mole(SRC) from its vapor pressure of 4.5X10-5 mm Hg(1) and water solubility of 133 mg/l(2). This Henry's Law constant indicates that 1,2-dinitrobenzene is expected to be essentially nonvolatile from water(3). 1,2-Dinitrobenzene's Henry's Law constant(1,2) indicates that volatilization from moist soil surfaces is not expected to occur(SRC). 1,2-Dinitrobenzene is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

Occupational exposure to 1,2-dinitrobenzene may occur through inhalation and dermal contact with this compound at workplaces where 1,2-dinitrobenzene is produced or used. (SRC)

Drug Information

Readily absorbed through the skin, either as solid, liquid, or vapor. /Dinitrobenzene/

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 - SE, 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 NADH. 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, INGESTION, OR SKIN ABSORPTION: Headache, vertigo and vomiting followed by exhaustion, numbness of the legs, staggering and collapse. Intense methemoglobinenia may lead to asphyxia severe enough to injure the CNS. EYES: Irritation. SKIN: Stains skin yellow. (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 1,2-DINITROBENZENE (9 total), please visit the HSDB record page.

1,2-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. Weakness. Blue lips, fingernails and skin. Headache. Dizziness. Nausea. Laboured breathing.


MAY BE ABSORBED! See Inhalation.


Redness. Pain.

Eyes, skin, blood, liver, cardiovascular system, central nervous system

1,2-Dinitrobenzene Use and Manufacturing

Methods of Manufacturing

Obtained from o-nitroaniline through diazotization and replacement. Add o-nitroaniline to the hydrochloric acid solution to dissolve, and drop the sodium nitrite solution below 7℃. Then add sodium fluoroborate solution, stir for 10min, filter out the nitrodiafluoroborate diazonium salt, and immediately wash with cold 5% sodium fluoroborate solution, methanol, ether. Add it to a mixture of sodium nitrite, copper powder, and water, and slowly add while stirring. Then steam distillation, the distillate is cooled, the crystals are filtered out, and air-dried to obtain o-dinitrobenzene. The yield was 69%.

Uses

1,2-Dinitrobenzene was used as internal standard for analysis of the explosives, TNT, RDX, and tetryl in sea water by vapor phase chromatography with the nickel-63 electron capture detector.

GRADES: TECHNICAL.

Hazardous organic and inorganic cmpd, incl o-dinitrobenzene, in water were determined by gas chromatography and mass spectroscopy.|OSW Method 8270B. Determination Semivolatile Organic compounds by Gas Chromatography/Mass Spectrometry (GC/MS): Capillary Column Technique. Detection limit = 40.0 ug/l.|OSW Method 8091. Nitroaromatics and Cyclic Ketones: Capillary Column Technique.

Fire Hazards -> Reactive - 4th degree

Computed Properties

Molecular Weight:168.11
XLogP3:1.7
Hydrogen Bond Acceptor Count:4
Exact Mass:168.01710661
Monoisotopic Mass:168.01710661
Topological Polar Surface Area:91.6
Heavy Atom Count:12
Complexity:173
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Recommended Suppliers of 1,2-Dinitrobenzene

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    CAS No.: 528-29-0
    Grade: Industrial Grade
    Content: 99%
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