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Home > Encyclopedia > 2,5-Dinitrotoluene

2,5-Dinitrotoluene

2,5-Dinitrotoluene structure

2,5-Dinitrotoluene 

structure
  • CAS No:

    619-15-8

  • Formula:

    C7H6N2O4

  • Chemical Name:

    2,5-Dinitrotoluene

  • Synonyms:

    Benzene,2-methyl-1,4-dinitro-;Toluene,2,5-dinitro-;2-Methyl-1,4-dinitrobenzene;2,5-Dinitrotoluene;2,5-DNT;1-Methyl-2,5-dinitrobenzene;3-Methyl-1,4-dinitrobenzene;NSC 159120

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

YELLOW-TO-ORANGE-YELLOW CRYSTALS WITH CHARACTERISTIC ODOUR.


YELLOW-TO-ORANGE-YELLOW CRYSTALS WITH CHARACTERISTIC ODOUR.

2,5-Dinitrotoluene Basic Attributes

182.135

182.13

210-581-4

870KS1U6JB

1591

159120

3454

DTXSID8027248

Needles from alcohol

Characteristics

91.6

2.03 (estimated)

YELLOW-TO-ORANGE-YELLOW CRYSTALS WITH CHARACTERISTIC ODOUR.

1.282 g/cm3 @ Temp: 111 °C

52.5 °C

284 °C

207°C c.c.

1.598

Solubility in water, g/100ml at 20°C: 0.03 (very poor)

Normally stored as a molten liquid. Separate from strong oxidizers & reducing agents. Hot water coils should not exceed 194 deg F (90 deg C). /Dinitrotoluenes/

0.0005 mm Hg at 25 deg C /extrapolated/

Relative vapour density (air = 1): 6.3

Potentially explosive if heated to decomposition temperatures in confined spaces or detonated. ... Organic contaminants lower decomposition temperatures & incr risk of explosion. /Dinitrotoluenes/

Henry's Law constant = 5.50X10-7 atm-cu m/mole at 25 °C (est)

Hydroxyl radical reaction rate constant = 1.9X10-13 cu cm/molecule-sec at 25 °C (est)

-3.4460E+09 J/kmol /Standard Net Heat of Comb/

Dust explosion possible if in powder or granular form, mixed with air.

Critical temperatuer: 814 deg K (est); critical pressure 3.4X10+06 Pa (est)

Safety Information

II

6

3454

R45

53-45-61

XT1750000

T: Toxic;N: Dangerous for the environment;

Fireproof. Separated from strong oxidants, food and feedstuffs and incompatible materials. See Chemical Dangers. Well closed. Keep in a well-ventilated room. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.

P201, P202, P260, P261, P264, P270, P271, P273, P280, P281, P301+P310, P302+P352, P304+P340, P308+P313, P311, P312, P314, P321, P322, P330, P361, P363, P391, P403+P233, P405, P501

H301

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.|SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.|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 DINITROTOLUENE IN PAPER OR OTHER FLAMMABLE MATERIAL & BURNING IN SUITABLE COMBUSTION CHAMBER WHICH ALLOWS BURNING IN UNCONFINED CONDITION & IS EQUIPPED WITH APPROPRIATE EFFLUENT GAS CLEANING DEVICE. 2) BY DISSOLVING IN FUEL OIL & ATOMIZING IN SUITABLE COMBUSTION CHAMBER EQUIPPED WITH APPROPRIATE EFFLUENT GAS CLEANING DEVICE. /DINITROTOLUENE/|Dinitrotoluene is a waste chemical stream constituent which may be subjected to ultimate disposal by controlled incineration. Pretreatment involves contact of the dinitrotoluene contaminated waste with sodium carbonate and solid combustibles followed by incineration in an alkaline scrubber equipped incinerator unit. /Dinitrotoluene/

USEPA; Ambient Water Quality Criteria Doc: Dinitrotoluene (1980) EPA 440/5-80-045|Rickert DE et al; CRC Crit Rev Toxicol 13 (3): 217-34 (1984). A review with 86 ref on the toxicity, mutagenicity, carcinogenicity, and metabolism of 2,3- 2,4-, 2,5-, 2,6-, 3,4-, and 3,5-dinitrotoluene in man and lab animals.|NIOSH; Current Intelligence Bulletin 44 Dinitrotoluenes (DNT) 20 pp. (7/5/85) DHHS Pub No 85-109.

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.

|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P273, P280, P281, P301+P310, P302+P352, P304+P340, P308+P313, P311, P312, P314, P321, P322, P330, P361, P363, P391, P403+P233, P405, and P501|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|Aggregated GHS information provided by 22 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P301+P312, P304+P340, P312, P330, P403+P233, P405, and P501|P260, P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P340, P309+P311, P312, P314, P321, P330, P332+P313, P362, P391, P403+P233, P405, and P501

Wear appropriate clothing to prevent any possibility or probability of skin contact with molten liquids or repeated or prolonged contact with solutions. Wear eye protection to prevent any possibility of eye contact with molten material.|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 any possibility of skin contact with molten or liquid dinitrotoluene, or liquids containing dinitrotoluene. /Dinitrotoluene/|Wear appropriate clothing to prevent any possibility or probability of skin contact with molten liquids or repeated or prolonged contact with solutions. Wear eye protection to prevent any possibility of eye contact with molten material. /Dinitrotoluene/|For more Personal Protective Equipment (PPE) (Complete) data for 2,5-DINITROTOLUENE (10 total), please visit the HSDB record page.

Combustible material. /3,4-Dinitrotoluene/|Material may explode when exposed to heat or flame. /3,4-Dinitrotoluene/

Potentially explosive if heated to decomposition temperatures in confined spaces or detonated. ... Organic contaminants lower decomposition temperatures & incr risk of explosion. /Dinitrotoluenes/

WATER, DRY CHEMICAL, OR CARBON DIOXIDE FROM PROTECTED LOCATION.|If material on fire or involved in fire: Use water in flooding quantities as fog. Use foam, dry chemical, or carbon dioxide. Apply water from as far a distance as possible. Keep run-off water out of sewers and water sources. /Dinitrotoluenes, molten/|If material on fire or involved in fire: Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Solid streams of water may be ineffective. Use foam, dry chemical, or carbon dioxide. /Dinitrotoluene, liquid; dinitrotoluene, solid/

1) REMOVE ALL IGNITION SOURCES. 2) VENTILATE AREA OF SPILL. 3) FOR SMALL QUANTITIES, SWEEP ONTO PAPER OR OTHER SUITABLE MATERIAL & BURN IN SUITABLE COMBUSTION CHAMBER WHICH ALLOWS BURNING IN UNCONFINED CONDITION & IS EQUIPPED WITH APPROPRIATE EFFLUENT GAS CLEANING DEVICE. LARGE QUANTITIES MAY BE RECLAIMED...IF...NOT PRACTICAL, DISSOLVE IN FUEL OIL & ATOMIZE IN SUITABLE COMBUSTION CHAMBER EQUIPPED WITH APPROPRIATE EFFLUENT GAS CLEANING DEVICE. /DINITROTOLUENE/|Environmental considerations - water spill: Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. Remove trapped material with suction hoses. If dissolved, in region of 10 ppm or greater concentration, apply activated carbon at ten times the spilled amount. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates. /Dinitrotoluene, liquid; dinitrotoluene, solid/|Environmental considerations - land spill: Cover solids with plastic sheet to prevent dissolving in rain or fire fighting water. /Dinitrotoluene, liquid; dinitrotoluene, solid/

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.|Eating and smoking should not be permitted in areas where dinitrotoluene or liquids containing dinitrotoluene are handled, processed, or stored. Employees who handle dinitrotoluene or liquids containing dinitrotoluene should wash their hands thoroughly with soap or mild detergent and water before eating, smoking, or using toilet facilities. /Dinitrotoluene/|... PROGRAM TO PREVENT HEALTH IMPAIRMENT DUE TO EXPOSURE TO AROMATIC NITRO-COMPOUNDS REQUIRES EXPOSURE CONTROL & MEDICAL SUPERVISION ... JOB ANALYSIS TO ENSURE PROPER HANDLING PROCEDURES, ADEQUATE EQUIPMENT DESIGN FOR ... OPERATING & MAINTENANCE, & APPROPRIATE VENTILATION WITH AIR-POLLUTION CONTROL ARE MINIMUM REQUIREMENTS. TOTALLY ENCLOSED SYSTEMS ARE PREFERRED. ... AIR ANAL CAN BE HELPFUL; BUT IN GENERAL, RESULTS HAVE BEEN MISLEADING DUE TO LOW VAPOR PRESSURE ... & CONTAMINATION OF SURFACES WHERE SKIN CONTACT OCCURS ... MIST FROM HOT CHARGES, LEAKING LINES, STEAMING OPERATIONS, HOT DRAINAGE DITCHES, ETC ... DRAINAGE CANNOT BE IGNORED AS SOURCES OF GROSS SKIN EXPOSURE ... /NITRO-CMPD, AROMATIC/|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 approved by the Mine Safety and Health Administration (formerly Mining Enforcement and Safety Administration) or by the National Institute for Occupational Safety and Health. /Dinitrotoluene/|For more Preventive Measures (Complete) data for 2,5-DINITROTOLUENE (15 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. /Dinitrotoluenes; Dinitrotoluenes, liquid; Dinitrotoluenes, molten; Dinitrotoluenes, 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. /Dinitrotoluenes; Dinitrotoluenes, liquid; Dinitrotoluenes, molten; Dinitrotoluenes, 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. /Dinitrotoluenes; Dinitrotoluenes, liquid; Dinitrotoluenes, molten; Dinitrotoluenes, 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. /Dinitrotoluenes; Dinitrotoluenes, liquid; Dinitrotoluenes, molten; Dinitrotoluenes, solid/|For more DOT Emergency Guidelines (Complete) data for 2,5-DINITROTOLUENE (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.

Permissible Exposure Limit: Table Z-1 8-hr Time-Weighted Avg: 1.5 mg/cu m. Skin Designation. /Dinitrotoluene/

NIOSH considers dinitrotoluene to be a potential occupational carcinogen. /Dinitrotoluene/|NIOSH usually recommends that occupational exposures to carcinogens be limited to the lowest feasible concentration. /Dinitrotoluene/|Recommended Exposure Limit: 10 Hour Time-Weighted Average: 1.5 mg/cu m, skin. /Dinitrotoluene/

Consult an expert! Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Sweep spilled substance into sealable containers. Carefully collect remainder. Then store and dispose of according to local regulations.

Fireproof. Separated from strong oxidants, food and feedstuffs and incompatible materials. See Chemical Dangers. Well closed. Keep in a well-ventilated room. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.

A harmful concentration of airborne particles can be reached quickly when dispersed.

The substance is irritating to the eyes, skin 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 the formation of methaemoglobin. This substance is possibly carcinogenic to humans.

NO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust.

AVOID ALL CONTACT!

Use local exhaust or breathing protection.

Protective clothing. Protective gloves.

Wear safety goggles.

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Dinitrotoluene is produced, as an intermediate or a final product, by process units covered under this subpart. /Dinitrotoluene/

| 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.| 3 - Materials that in themselves are capable of detonation or explosive decomposition or explosive reaction but that require a strong initiating source or must be heated under confinement before initiation.

Samples from 6 industrial wastewater drains which outflow into Dokai Bay, Kitakyushu City, Japan were collected in 1979. 2,5-Dinitrotoluene was not detected in 5 samples and the concentration in the positive sample was 7.5 ppb. The estimated daily discharge into the bay is 580 g/day(1). 2,5-Dinitrotoluene was detected in 70.9% of the 54 samples of condensate water collected from a TNT manufacturing facility at a range of 0.01-0.60 mg/L; a minimum of one sample per week was collected over a one year period(2).

Toxicity

LD50 Rat oral 707 mg/kg|LD50 Rat oral 517 mg/kg|LD50 Mouse oral 652 mg/kg

Those individuals with blood or liver disorders may be at increased risk from exposure to 2,4-DNT. /2,4-Dinitrotoluene/

2,5-Dinitrotoluene's production during the manufacturing of toluene diisocyanate(1) may result in its release to the environment through various waste streams(SRC); the 2,5-dinitrotoluene is formed as an impurity in the commercial dinitrotoluene mixture used to produce toluene diisocyanate(1).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 575(SRC), determined from a structure estimation method(2), indicates that 2,5-dinitrotoluene is expected to have medium mobility in soil(SRC). Volatilization of 2,5-dinitrotoluene from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant estimated as 5.5X10-7 atm-cu m/mole(SRC), derived from its extrapolated vapor pressure, 5X10-4 mm Hg at 25 deg(3), and water solubility, 219 mg/L(4). 2,5-Dinitrotoluene is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure. 2,5-Dinitrotoluene may be susceptible to photolysis on surfaces exposed to sunlight based on the behavior of structurally similar 2,4-dinitrotoluene which had sunlight photolysis half-lives of 43 hr in distilled water and 2.7, 9.6, and 3.7 hr in river, bay, and pond waters, respectively(5) and its quantum yield of 0.00672 at 313 nm(6). Biodegradation data specific to 2,5-dinitrotoluene are limited; however, biodegradation is expected to be an important fate process for structurally similar 2,4-dinitrotoluene based on results various screening tests that demonstrated microbial degradation(7-11).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 575(SRC), determined from an estimation method(2), indicates that 2,5-dinitrotoluene is expected to adsorb moderately to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected to be slow(3) based upon an estimated Henry's Law constant of 5.5X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 5X10-4 mm Hg at 25 °C(3), and water solubility, 219 mg/L(4). Using this Henry's Law constant and an estimation method(5), volatilization half-lives for a model river and model lake are 90 and 660 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 13(SRC), from an estimated log Kow of 2.18(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low. 2,5-Dinitrotoluene is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(5). In aqueous solution, 2,5-dinitrotoluene has a quantum yield of 0.00672 at 313 nm(7) indicating that it is susceptible to direct photolysis by sunlight(SRC). 2,4-dinitrotoluene (which has a similar quantum yield as 2.5-dinitrotoluene) had sunlight photolysis half-lives of 43 hr in distilled water and 2.7, 9.6, and 3.7 hr in river, bay, and pond waters, respectively(8). Biodegradation data specific to 2,5-dinitrotoluene are limited; however, biodegradation is expected to be an important fate process for structurally similar 2,4-dinitrotoluene based on results various screening tests that demonstrated microbial degradation(9-13).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,5-dinitrotoluene, which has an extrapolated vapor pressure of 5.0X10-4 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere at temperatures above 25 °C. At temperatures below 15 °C, the gas/particle partitioning model predicts that 2,5-dinitrotoluene will exist in both the vapor and particulate phases. Vapor-phase 2,5-dinitrotoluene 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 84 days(SRC), calculated from its rate constant of 1.90X10-13 cu cm/molecule-sec at 25 °C(SRC), determined using a structure estimation method(3). Particulate-phase 2,5-dinitrotoluene may be removed from the air by wet or dry deposition(SRC). 2,5-Dinitrotoluene is susceptible to direct photolysis in sunlight(4).

The rate constant for the vapor-phase reaction of 2,5-dinitrotoluene with photochemically-produced hydroxyl radicals has been estimated as 1.9X10-13 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 84 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2,5-Dinitrotoluene is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2). In aqueous solution, 2,5-dinitrotoluene has a quantum yield of 0.00672 at 313 nm(3) indicating that it is susceptible to direct photolysis by sunlight(SRC). Photolysis of 1.0 ppm 2,4-dinitrotoluene in distilled and natural waters gave half-lives of 43 hr in distilled water and 2.7, 9.6, and 3.7 hr in river, bay and pond waters, respectively(4); 2,4-dinitrotoluene has a similar quantum yield in water as 2,5-dinitrotoluene(3).

An estimated BCF of 13 was calculated for 2,5-dinitrotoluene(SRC), using an estimated log Kow of 2.18(1) and a regression-derived equation(1). The BCF for dinitrotoluene (mixed isomers) has been measured to be low (BCF values of 0.6 to 21.2) in carp (Carprinus carpio)(2). According to a classification scheme(2), these BCF values suggest the potential for bioconcentration in aquatic organisms is low.

Using a structure estimation method based on molecular connectivity indices(1), the Koc for 2,5-dinitrotoluene can be estimated to be 575(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2,5-dinitrotoluene is expected to have medium mobility in soil.

The Henry's Law constant for 2,5-dinitrotoluene is estimated as 5.5X10-7 atm-cu m/mole(SRC) derived from its vapor pressure, 5X10-4 mm Hg at 25 °C(1), and water solubility, 219 mg/L(2). This Henry's Law constant indicates that 2,5-dinitrotoluene is expected to volatilize slowly from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 90 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 660 days(SRC). 2,5-Dinitrotoluene's estimated Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to be an important fate process(SRC). 2,5-Dinitrotoluene is not expected to volatilize from dry soil surfaces based upon its vapor pressure(SRC).

Occupational exposure to 2,5-dinitrotoluene may occur through dermal contact with this compound at workplaces where 2,5-dinitrotoluene is produced or used. (SRC)

Drug Information

The metabolites produced from 5 DNT isomers (2,3-, 2,4-, 2,5-, 2,6- and 3,4-DNT) by Escherichia coli strain W3110, isolated from human intestine, were identified. Data obtained from metabolites produced by the Escherichia coli were 2 monoaminonitrotoluenes and hydroxylaminonitrotoluenes in all cases. This finding indicates that DNT is reduced via hydroxylaminonitrotoluenes to monoaminonitrotoluenes in Escherichia coli. In addn, the redn reactivities of DNT isomers were 3- > 2- for 2,3-DNT, 4- > 2- for 2,4-DNT, 5- > 2- for 2,5-DNT and 3- > 4- for 3,4-DNT.|Bioactivation of dinitrotoluene in the rat is thought to occur by the following processes: The methyl group is oxidized to an alcohol by a cytochrome p450 dependent pathway; the benzyl alcohol is conjugated with glucoronic acid and excreted in the bile. Intestinal microflora hydrolyze the glucuronide and reduce one nitro group, forming an aminonitrobenzyl alcohol which can be readsorbed from the intestine. The amino group oxidized to an hydroxylamine by hepatic enzymes and conjugated with sulfate. Decomposition of the sulfate ester yields a highly electrophilic nitrenium (or carbonium) ion which can react with DNA and other biological nucleophiles.

Fresh air, rest. Refer for medical attention.


Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .


Rinse with plenty of water for several minutes (remove contact lenses if easily possible).

In case of ingestion, induction of emesis is not recommended because of the potential for central nervous system depression. Gastric lavage and administration of activated charcoal may be considered soon after ingestion, provided airways are protected. /Dinitrotoluene/|Methemoglobinemia may be treated with methylene blue in symptomatic patients, methemoglobin levels exceeding 20% to 30% or lower in patients with predisposing conditions such as anemia, and respiratory and heart diseases. Hyperbaric oxygen or exchanged transfusion may be considered in refractory patients or when contraindication to administration of methylene blue exists (eg, G6PD deficiency). /Dinitrotoluene/|Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Aniline and related compounds/|Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). 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 0.9% saline (NS) 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, has severe pulmonary edema, or is in severe respiratory distress. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if hypotensive with a normal fluid volume. 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. ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aniline and related compounds/

/SIGNS AND SYMPTOMS/ Causes severe eye & skin burns. /Dinitrotoluenes/

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.

Cough. Sore throat. Blue lips, fingernails and skin.


MAY BE ABSORBED! Redness. Pain.


Redness. Pain.

2,5-Dinitrotoluene Use and Manufacturing

Methods of Manufacturing

Dinitration of toluene results in the formation of a number of isomeric products, and with a typical sulfuric-nitric acid nitrating mixture the following mixture of isomers is obtained: 75 wt% 2,4-dinitrotoluene, 19 wt% 2,6-dinitrotoluene, 2.5 wt% 3,4-dinitrotoluene, 1wt% 2,3-dinitrotoluene, and 0.5 wt% 2,5-dinitrotoluene.

Uses

Dinitrotoluenes are used as intermediates for the production of toluene diisocyanate and dyestuffs; they also are used as explosives. Dinitrotoluene as an isomeric mixture is manufactured in large scale continuous plants for direct conversion to toluene diamine (TDA) for production of toluene diisocyanate; 2,5-dinitrotoluene typically exists as an impurity at about 0.5 wt% of the isomeric mixture.

Production

Benzene, 2-methyl-1,4-dinitro- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5423]

Benzene, 2-methyl-1,4-dinitro-: ACTIVE|Analysis of technical grade dinitrotoluene yielded the following results: 76.49% 2,4-DNT, 18.83% 2,6-DNT, 0.65% 2,5-DNT, 2.43% 3,4-DNT, 1.54% 2,3-DNT, 0.040% 3,5-DNT, 0.050% Trinitrotoluene, 0.005% cresols, 0.003% mononitrobenzene, and 0.003%, 0.0005%, and 0.006%, for ortho-, meta-, and para-, mononitrotoluenes, respectively.|Dinitrification of toluene typically yields 0.5% of 2,5-dinitrotoluene by weight.

DINITROTOLUENE & ITS ISOMERS WERE DETERMINED IN WATER SAMPLES BY GC.|HPLC TECHNIQUES WERE USED IN LOW LEVEL DETECTION OF 2,5-DNT.

Computed Properties

Molecular Weight:182.13
XLogP3:2.7
Hydrogen Bond Acceptor Count:4
Exact Mass:182.03275668
Monoisotopic Mass:182.03275668
Topological Polar Surface Area:91.6
Heavy Atom Count:13
Complexity:220
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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