2,3,4,5-Tetrachloronitrobenzene

log Kow = 3.93

3.93

Solubility: 28.0 mg/L (water) /Tetrachloronitrobenzene/

In water, 7.31 mg/L at 20 °C

2,3,4,5-tetrachloronitrobenzene appears as pale yellow crystals. (NTP, 1992)

Pale yellow solid; [CAMEO]

This chemical does not meet GHS hazard criteria for 7% (3 of 43) of reports.

Warning

H302 (93%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 43 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Courtney KD et al; Toxicol Appl Pharmacol 35: 239-56 (1976). Effects of pentachlorobenzene, hexachlorobenzene and related compounds on fetal development.

USEPA; ECAO Hazard Profile: Tetrachloronitrobenzene (1980)

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.

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then dampen the solid spill material with toluene and transfer the dampened material to a suitable container. Use absorbent paper dampened with toluene t pick up any remaining material. Your contaminated clothing and the absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent-wash all contaminated surfaces with toluene followed by washing with soap and water solution. All exposed surfaces should be analyzed for contamination. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant life; and conformance with environmental and public health regulations.

Group I Containers: Combustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) should be disposed of in pesticide incinerators or in specified landfill sites. /Organic or metallo-organic pesticides/

Group II Containers: Non-combustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) must first be triple-rinsed. Containers that are in good condition may be returned to the manufacturer or formulator of the pesticide product, or to a drum reconditioner for reuse with the same type of pesticide product, if such reuse is legal under Department of Transportation regulations (eg 49 CFR 173.28). Containers that are not to be reused should be punctured ... and transported to a scrap metal facility for recycling, disposal or burial in a designated landfill. /Organic or metallo-organic pesticides/

Seal all wastes in vapor-tight plastic bags for eventual disposal.

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Wear protective gloves when handling the concentrate.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3,300(SRC), determined from a log Kow of 3.93(2) and a regression-derived equation(3), indicates that 2,3,4,5-tetrachloronitrobenzene is expected to have slight mobility in soil(SRC). Volatilization of 2,3,4,5-tetrachloronitrobenzene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.3X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(4). However, adsorption to soil is expected to attenuate volatilization(SRC). 2,3,4,5-Tetrachloronitrobenzene is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.38X10-4 mm Hg(SRC), determined from a fragment constant method(5). Based on the data for the structural analog pentachloronitrobenzene, which degraded about 20% in three different soils over a period of 2 months(6), biodegradation is not expected to be an important environmental fate process in soil(SRC)

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3,300(SRC), determined from a log Kow of 3.93(2) and a regression-derived equation(3), indicates that 2,3,4,5-tetrachloronitrobenzene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 2.34X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 1.8 days and 25 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The volatilization half-life from a model pond is about 360 days when adsorption is considered(5). According to a classification scheme(6), a BCF of 142 measured in rainbow trout(2), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Biodegradation of 2,3,4,5-tetrachloronitrobenzene in water may be an important environmental fate process(SRC), based on the data for the structural analog pentachloronitrobenzene, which exhibited a half-life of 5 to 6 days in estuarine water(7).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,3,4,5-tetrachloronitrobenzene, which has an estimated vapor pressure of 1.38X10-4 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,3,4,5-tetrachloronitrobenzene 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 2,200 days(SRC), calculated from its rate constant of 7.2X10-15 cu cm/molecule-sec at 25 °C (SRC) that was derived using a structure estimation method(3). 2,3,4,5-Tetrachloronitrobenzene contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

The Koc of 2,3,4,5-tetrachloronitrobenzne is estimated as 3,300(SRC), using a log Kow of 3.93(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2,3,4,5-tetrachloronitrobenzene is expected to have slight mobility in soil.

The contamination of Mississippi River fish with chlorinated nitrobenzenes appears to be localized in a 150 mi section of the river extending from St. Louis, MO, to Cape Girardeau, MO; no chlorinated nitrobenzenes (< 0.005 ppm) were detected in Mississippi River fish caught above or below this region of the river or in fish from the lower Missouri River, which joins the Mississippi River near St. Louis.

AEROBIC: Based on the biodegradation data for the structural analog pentachloronitrobenzene, biodegradation of 2,3,4,5-tetrachloronitrobenezene in soil is expected to be slow(SRC). Pentachloronitrobenzene at 100 ppm and incubated in a fine sandy loam, a clay soil, and a peat muck showed about 20% biodegradation over 2 months for all soils(1). A laboratory half-life ranging from 213-699 days with an average of 468 days was reported for soil with two application rates, (10 and 60 kg/ha) with a similar half-life reported for both rates(2). In flooded soils after 1 month of incubation, 27, 67, and 93% of the applied pentachloronitrobenzene was lost from Columbia fine sandy loam, Sacramento clay, and Staten peaty muck, respectively; sterile controls had a much lower rate of degradation(1). In a sediment:water system collected from the Davis Bayou, MS, a first order biodegradation rate constant of 0.00456-0.00481/hr was measured for pentachloronitrobenzene (half-life of 6-7 days); a rate constant of 0.00380 was measured for a sterile sediment:water system(3). In estuarine water alone, a first order biodegradation rate constant of 0.00554-0.00633/hr was measured for pentachloronitrobenzene (half-life of 5-6 days), with a rate constant of 0.00445/hr measured for a sterile water control(3).

ANAEROBIC: 2,3,4,5-Tetrachloronitrobenzene is expected to biodegrade under anaerobic conditions, based on the data for the structural analog pentachloronitrobenzene(SRC). An anaerobic, estuarine, sulfidogenic sediment, collected from the Tsurumi River, Japan, biodegraded pentachloronitrobenzene with a first-order rate constant of 0.866/day and a half-life of 0.8 days; an autoclaved sediment sample had a degradation rate constant of 0.0781/day(1). Anaerobic degradation of pentachloronitrobenzene, using loose, moist plow layer of soil pH of 5.5-6.5, required from 6-18 weeks to reach 90% degradation(2).

A BCF value of 142 was measured in rainbow trout after 36 days exposure under continuous flow conditions and a water concentration of 610 ng/L(1). According to a classification scheme(2), this BCF value suggests that bioconcentration in aquatic organisms is high(SRC).

The Henry's Law constant for 2,3,4,5-tetrachloronitrobenzene is estimated as 2.3X10-5 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2,3,4,5-tetrachloronitrobenzene is expected to volatilize from water surfaces(2). 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)(2) is estimated as 1.8 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)(2) is estimated as 25 days(SRC). 2,3,4,5-Tetrachloronitrobenzene's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The volatilization half-life from a model pond is about 360 days when adsorption is considered(3). 2,3,4,5-Tetrachloronitrobenzene is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.38X10-4 mm Hg(SRC), determined from a fragment constant method(4).

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Skin of mice was pretreated with croton oil to promote production of papillomas. 2,3,4,5-tetrachloronitrobenzene was then applied to skin to test for tumorigenic activity. Increase in papillomas was obtained.

/OTHER TOXICITY INFORMATION/ ... TCNB /tetrachloronitrobenzene/ produced larger number of papillomas than pentachloronitrobenzene when applied to skin and then followed by croton oil treatment.

The rate constant for the vapor-phase reaction of 2,3,4,5-tetrachloronitrobenzene with photochemically-produced hydroxyl radicals has been estimated as 7.2X10-15 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2200 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2,3,4,5-Tetrachloronitrobenzene is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). 2,3,4,5-Tetrachloronitrobenzene contains chromophores that absorb at wavelengths >290 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).

2,3,4,5-Tetrachloronitrobenzene's production and use as a chemical intermediate may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 1.4X10-4 mm Hg at 25 °C indicates 2,3,4,5-tetrachloronitrobenzene will exist solely as a vapor in the atmosphere. Vapor-phase 2,3,4,5-tetrachloronitrobenzene will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 2,200 days. 2,3,4,5-Tetrachloronitrobenzene contains chromophores that absorb at wavelengths >290 nm and therefore may be susceptible to direct photolysis by sunlight. If released to soil, 2,3,4,5-tetrachloronitrobenzene is expected to have slight mobility based upon an estimated Koc of 3,300. Volatilization from moist soil surfaces is expected to be an important fate process based upon an estimated Henry's Law constant of 2.3X10-5 atm-cu m/mole. However, absorption to soil is expected to attenuate volatilization. 2,3,4,5-Tetrachloronitrobenzene is not expected to volatilize from dry soil surfaces based upon its vapor pressure. Based an the data for the structural analog pentachloronitrobenzene, which degraded 90% in 6-18 weeks in anaerobic, loose, moist plow layer of soil and 18 weeks to 3 years to biodegrade in the same soil under aerobic conditions, biodegradation is not expected to be an important environmental fate process. If released into water, 2,3,4,5-tetrachloronitrobeznene is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Again, based on data for the structural analog pentachloronitrobenzene, which exhibited a half-life of 5 to 6 days in estuarine water, biodegradation may be an important environmental fate process in some aquatic systems. Volatilization from water surfaces is expected to be an important fate process based upon this compound's estimated Henry's Law constant. However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. An estimated BCF of 142 suggests the potential for bioconcentration in aquatic organisms is high. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Occupational exposure to 2,3,4,5-tetrachloronitrobenzene may occur through dermal contact with this compound at workplaces where 2,3,4,5-tetrachloronitrobenzene is produced or used. (SRC)

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. /Aromatic hydrocarbons 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 pulmonary edema and treat if necessary ... . 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 patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aromatic hydrocarbons 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. Consider drug therapy for pulmonary edema ... . Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias if 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. Watch for signs of fluid overload ... .Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aromatic hydrocarbons and related compounds/

Unabsorbed 2,3,4,5-TCNB was reduced, in large measure, in the gut to an amine which diazotizes readily and couples. Absorbed TCNB was partly converted to glucuronide (27% of dose) and to ethereal sulfate (7% of dose). 2,3,4,5-Tetrachloroaniline was isolated from urine.

2,3,4,5-Tetrachloronitrobenzene was reduced in the gastrointestinal contents of rabbits to 2,3,4,5-tetrachloroaniline.

There appear to be two major pathways for the metabolism of nitrobenzene and substituted nitrobenzenes. The first of these is reduction of the nitro group to yield aniline or substituted anilines. For nitrobenzene and perhaps for pentachloronitrobenzene, reduction of the nitro group to the amine is accomplished by bacteria of the gastrointestinal tract. Addition of a second nitro group results in easier reduction of one of the nitro groups on dinitrobenzenes, since they can be reduced under aerobic conditions by hepatic and erythrocyte enzymes. Bacterial reduction of the dinitrobenzenes is probably not quantitatively important in vivo. The second pathway is replacement of a nitro group by glutathione. The relative importance of this pathway compared to nitro group reduction depends upon the compound. It has not been demonstrated to occur for nitrobenzene. It is the major route of metabolism for 1,2-dinitrobenzene but is not an important route for 1,3- or 1,4-dinitrobenzene in hepatocytes. Tetrachloronitrobenzene isomers in which the nitro group is flanked by chlorines and pentachloronitrobenzene undergo nitro group replacement, but 2,3,4,5-tetrachloronitrobenzene does not. ...

The metabolism of pentachloronitrobenzene (PCNB) in rats was studied. Metabolites isolated from rat excreta and identified were: N-acetyl-S-(pentachlorophenyl)cysteine, pentachlorothiophenol, pentachlorothioanisole, 2,3,4,5-tetrachlorothiophenol, 2,3,4,5-tetrachlorothioanisole, 2,3,4,6- and/or 2,3,5,6-tetrachloro-thiophenol and -thioanisole, 1,4-bis(methylthio)tetrachlorobenzene, 1,4-dimercapto-tetrachlorobenzene and/or 4-methylthio-tetrachlorothiophenol, pentachlorophenol, pentachloroanisole, 2,3,4,5-tetrachlorophenol, 2,3,4,5-tetrachloroanisole, 2,3,4,6- and/or 2,3,5,6-tetrachloro-phenol and -anisole, pentachlorobenzene, 2,3,4,5-tetrachloronitrobenzene, pentachloroaniline and 2,3,4,5-tetrachloroaniline.

This isomer exhibited greater absorption in rabbits than the 2,3,5,6-isomer.

Tetrachloronitrobenzene is not readily absorbed by animals exposed to concn of 0.1 to 3.0 g/kg. ... The primary route of elimination appears to be in the feces. /Tetrachloronitrobenzene/

Used in organic synthesis, including anthraquinone vat dyes; Also used in UV oxidation, stabilizers for plastics, and experimental antineoplastic drugs; [HSDB]

In organic synthesis.

As an experimental antineoplastic drug

Intermediate, including anthraquinone vat dyes, UV oxidation, stabilizers for plastics.

(1977) NOT PRODUCED COMMERCIALLY IN US

(1979) NOT PRODUCED COMMERCIALLY IN US

DB-905

FOLOSAN DB-905 FUMITE

FOLSAN

... 2,3,4,5-TETRACHLORONITROBENZENE IS LESS FUNGICIDAL & MORE PHYTOTOXIC THAN 2,3,5,6-TETRACHLORONITROBENZENE.

Dechlorination catalysts for polychloronitrobenzenes and polychloroanilines contained copper and a Group VIII metal on Al2O3. Thus, Al2O3 with a sq surface area of 300 sq m/g was treated with 6% Cu as CuC12 and 0.5% Ir as H2IrCl2. The resulting catalyst was used to dechlorinate 2,3,4,5-tetrachloronitrobenzene at 310 degree to give 2,3,4,5-Cl4C6HNH2 4.7 mol %. ...

Derivatives: mesidene, trimesic acid, 2,4,6-tris(3,5-di-t-butyl-4-hydroxybenzyl)mesitylene