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Home > Encyclopedia > 1,2,4,5-Tetrachlorobenzene

1,2,4,5-Tetrachlorobenzene

1,2,4,5-Tetrachlorobenzene structure

1,2,4,5-Tetrachlorobenzene 

structure
  • CAS No:

    95-94-3

  • Formula:

    C6H2Cl4

  • Chemical Name:

    1,2,4,5-Tetrachlorobenzene

  • Synonyms:

    Benzene,1,2,4,5-tetrachloro-;1,2,4,5-Tetrachlorobenzene;s-Tetrachlorobenzene;NSC 27003

  • Categories:

    Organic Chemistry  >  Hydrocarbons and Derivatives

Description

white solid


1,2,4,5-Tetrachlorobenzene is a chemical pollutant present in soils around wastewater treatment plants.


1,2,4,5-tetrachlorobenzene appears as odorless white flakes or chunky solid. (NTP, 1992)|COLOURLESS CRYSTALS.


1,2,4,5-tetrachlorobenzene appears as odorless white flakes or chunky solid. (NTP, 1992)|1,2,4,5-tetrachlorobenzene is a tetrachlorobenzene carrying chloro groups at positions 1, 2, 4 and 5.

1,2,4,5-Tetrachlorobenzene Basic Attributes

215.89

215.89

1618315

202-466-2

5N27529KGH

0676

27003

3077

DTXSID7024320

COLORLESS SUBLIMABLE NEEDLES

29036990

Characteristics

0

4.9

Light pink to gray Crystalline Solid

183.3 g/cm3

139.5 °C

244.5 °C

>230 °F

1.583

H2O: insoluble . <0.1 g/100 mL at 21 ºC

0-6°C

Vapour pressure, Pa at 25°C: 0.7

Relative vapour density (air = 1): 7.4

Oral-rat LD50: 1500 mg/kg;Oral-Mouse LD50: 1035 mg/kg

Open flames are flammable; high heat decomposes toxic chloride fumes; works with oxidants

STRONG, UNPLEASANT ODOR

1.00e-03 atm-m3/mole|Henry's Law constant = 1.0X10-3 atm-cu m/mol at 20 °C

NEEDLES, MONOCLINIC PRISMS FROM ETHER, ALCOHOL OR BENZENE

Insoluble in water.

Aryl Halides

1,2,4,5-TETRACHLOROBENZENE is incompatible with strong oxidizing agents. Reacts violently with sodium hydroxide in methanol. Several explosions have occurred during alkaline hydrolysis. (NTP, 1992)

221.8 J/g

Critical temp: 489.8 °C; critical pressure: 3380 kPa

Safety Information

I; II; III

9

UN 3077 9/PG 3

3

22-36/37/38-23/24/25-11-36-20/21/22-51/53

26-36-45-27-16-36/37-61

DB9450000

Xn,T,F,N

Treasury is ventilated at low temperature and dry; stored separately from oxidants and food additives

Stable. Combustible. Incompatible with strong oxidizing agents. Reacts explosively with alkaline methanol solutions.

P261-P273-P305 + P351 + P338-P501

H302-H315-H319-H335-H410

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U207, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.|A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids. A potential candidate for liquid injection incineration at a temperature range of 650 to 1,600 °C and a residence time of 0.1 to 2 seconds.|The following wastewater treatment technologies have been investigated for 1,2,4,5-tetrachlorobenzene: Biological treatment.

... Serious accidents have occurred during the commercial preparation of 2,4,5-trichlorophenol by alkaline partial hydrolysis of 1,2,4,5-tetrachlorobenzene during the period 1949 to 1976 ... The earlier process used methanolic alkali under autogenous pressure to effect the hydrolysis, and on 2 occasions around 1949 the reaction at 125 °C went out of control, one attaining 400 °C. ... In a further incidents in 1953, the explosion was associated with the post reaction stage during distillation of methanol from the reaction mixture. The later process used ethylene glycol as solvent to effect hydrolysis with sodium hydroxide and operated essentially at or near atmosphere pressure. ... Violent decomposition could ... occur during the subsequent solvent distillation phase in the absence of effective temp control. A laboratory residue from vacuum stripping using electric heating (without knowledge of the liquid temp) exploded when the vapor temp had reached 160 °C. In the Coalite plant incident in 1968, where the hydrolysis was run at about 180 °C in a reaction vessel heated by circulating oil at 300 °C, failure of the manually regulated oil heating system led to an uncontrollable temp incr during 50 min to above 250 °C, when a violent explosion occurred.|... CAN REACT VIGOROUSLY WITH OXIDIZING MATERIALS.

USEPA; Ambient Water Quality Criteria Doc: Chlorinated Benzenes (1980) EPA 440/5-80-028|USEPA; Health Assessment Document: Chlorinated Benzenes (1985) EPA 600/8-84-015|51 FR 24657-67 (1986) Chlorinated benzenes; final test rule|DHHS/NTP; NTP Report on the Toxicity Studies of 1,2,4,5-Tetrachlorobenzene in F344/N Rats and B6C3F1 Mice (Feed Studies) NTP TOX 7 (1991) NIH Pub No. 91-3126

UN 3077

This chemical is combustible. (NTP, 1992)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Risk of fire and explosion on contact with oxidizing agents.

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 89 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P261, P263, P264, P270, P271, P281, P301+P312, P304+P340, P308+P313, P312, P314, P330, P403+P233, P405, and P501

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: 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 a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a 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 protect this material from exposure to light. Store it under refrigerated temperatures, and keep it away from oxidizing materials and alkalies. (NTP, 1992)

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 appropriate chemical protective gloves, boots and goggles. /Chlorobenzene/

Combustible when exposed to heat or flame.

/USE/ CARBON DIOXIDE /&/ DRY CHEMICAL.

Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. Apply universal gelling agent to immobilize spill. Apply appropriate foam to diminish vapor and fire hazard. /Chlorobenzene/|Environmental considerations: Water spill: Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. If dissolved, in region of 10 ppm or greater concn, apply activated carbon at ten times the spilled amount. Remove trapped material with suction hoses. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates. /Chlorobenzene/|Environmental considerations: Air spill: Apply water spray or mist to knock down vapors. Combustion products include corrosive or toxic vapors. /Chlorobenzene/

If material /is/ not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock down vapors. /Chlorobenzene/|Avoid breathing vapors. Keep upwind. /Chlorobenzene/|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. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. /Chlorobenzene/|/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Health: May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. /Chlorobenzene/|/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /Chlorobenzene/|/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. /Chlorobenzene/|For more DOT Emergency Guidelines (Complete) data for 1,2,4,5-TETRACHLOROBENZENE (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.

Personal protection: P2 filter respirator for harmful particles. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting.

Separated from strong oxidants.

Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly on spraying or when dispersed, especially if powdered.

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

NO open flames.

Use local exhaust.

Protective gloves.

Wear safety goggles.

| 1 - Materials that, under emergency conditions, can cause significant irritation.| 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.| 0 - Materials that in themselves are normally stable, even under fire conditions.

U207; A toxic waste when a discarded commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or manufacturing chemical intermediate.

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 5000 lb or 2270 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).

U207; As stipulated in 40 CFR 261.33, when 1,2,4,5-tetrachlorobenzene, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

Concentrations of 0.3 to 2 ng/l (mean concentration 1.2 ng/l) were reported in waste water effluents from 4 treatment plants discharging into Lake Ontario and the Grand River(1). An unidentified isomer of tetrachlorobenzene was qualitatively identified in an effluent from a sewage treatment plant(2). 1,2,4,5-Tetrachlorobenzene was identified, not quantified, in effluent from the organic chemical industry in the US from 1979 to 1982(3). 1,2,4,5-Tetrachlorobenzene was found at concn of 81, 80, and 550 ng/cu m in the raw flue gas (up-stream from the electrostatic precipitator) from three runs under different conditions of a Swedish hazardous waste incinerator which was burning chlorinated waste, mostly solvents(4).|Combined tetrachlorobenzene isomers were detected at concns of 38-1,800,000 ng/cu m in the effluent of a waste gasification and combustion pilot plant(1) and detected at concns of 74.7 and 48 ng/cu m in the effluent of a hazardous waste incinerator in Biebesheim, Germany(2). 1,2,4,5-Tetrachlorobenzene was identified, not quantified, in pulp mill effluents in Canada(3). Combined tetrachlorobenzene isomers were detected at concns of 29 and 57 ug/cu m in the effluent of municipal refuse incinerators located in Virginia and Ohio, respectively(4). 1,2,4,5-Tetrachlorobenzene was detected at concns of 450 and 100 ppb in the ash of municipal waste incinerators in the US(5).

1,2,4,5-Tetrachlorobenzene was detected in the sediment of Lake Ketelmeer, Netherlands at concns of 45 and 20 ng/kg(1). Mean 1,2,4,5-tetrachlorobenzene concns of 0.3, 1, 1 and 52 ppb were reported in the surficial sediments from Lakes Superior, Huron, Erie, and Ontario, respectively(2). Combined 1,2,3,5- and 1,2,4,5-tetrachlorobenzene was detected at concns of 0-0.4 ng/g in sediment from Ise Bay, Japan(3). 1,2,4,5-Tetrachlorobenzene was detected at a max concn of 21 ng/g in sediment taken from the Scheldt estuary, Netherlands(4). Combined 1,2,3,5- and 1,2,4,5-tetrachlorobenzene was detected in soil samples in Niagara Falls, NY at mean concns of 910, 4,620, 2,000, 1,300 and 290 pg/g(5). Sediment from the St Lawrence River contained 1,2,4,5-tetrachlorobenzene at concns of 0.18-2.1 ng/g(6). 1,2,4,5-Tetrachlorobenzene was detected in sediment(42 ng/g) and suspended particulate matter (14 ng/g) in Lake Ontario(7). Combined isomers of 1,2,3,5- and 1,2,4,5-tetrachlorobenzne were detected in sediment off the coast of Taiwan at concns of 1-12 ng/g(8).|Mean concentrations of 0.3, 1, 1, and 52 ppb were detected in surficial sediments from Lake Superior, Lake Huron, Lake Erie and Lake Ontario, respectively(1). Concentrations of 0.6 to 210 ppb found in a Lake Ontario sediment core (0 to 8 cm in depth) with the higher concentration in the upper 2 cm(1). Concentration of 17 ng/g detected in the settling particulates at a station on Lake Ontario(2). Concentrations ranging from 7 to 24 ng/g detected in suspended sediments collected at 6 locations of the Niagara River in 1982(3). Concentrations ranging from 13 to 21 ng/g detected in suspended sediment of Lake Ontario at depths from 20 to 68 meters with an average concentration of 68 ng/g found on bottom sediment(3). Unidentified isomers of tetrachlorobenzene identified at levels from not detected to 70 ng/g in the suspended sediment of the Niagara River in 1981(4). Qualitative detection reported for sediments collected in a canal in Berlin, Germany(5). Qualitative detection reported for both soil and sediment collected near the Love Canal(6). The ranges and mean concn (dry wt basis) of 1,2,4,5-tetrachlorobenzene detected in sediments taken from the following Great Lakes area in 1980 and 1982 were: southern Lake Huron, 0.3-1.7 ppb, 1.1 ppb avg; Lake St. Clair, 3.3-7.8 ppb, 5.6 ppb avg; western Lake Erie; 0.6-5.3 ppb, 1.7 ppb avg; central Lake Erie, 0.2-0.9 ppb, 0.6 ppb avg; and eastern Lake Erie, 0.2-1.0 ppb, 0.6 ppb avg(7).|SEDIMENT SAMPLES FROM THE WESTERN PORTION OF LAKE ONTARIO WERE COLLECTED IN OCTOBER 1980. THE SAMPLES WERE ANALYZED FOR CHLORINATED ORGANIC COMPOUNDS USING GC/MS. MANY OF THE CHLORINATED COMPOUNDS PREVIOUSLY FOUND TO BE LEAKING INTO THE NIAGARA RIVER FROM WASTE DISPOSAL SITES IN THE CITY OF NIAGARA FALLS WERE IDENTIFIED IN THE SEDIMENTS OF LAKE ONTARIO. THE COMPOUNDS (INCLUDING PENTACHLOROBENZENE) SHOWED A TENDENCY TO ACCUMULATE IN THE ZONES OF HIGH SEDIMENTATION IN BOTH THE NIAGARA AND MISSISSAUGA BASINS. THE AVERAGE RELATIVE CONCENTRATIONS OF TRI, TETRA, PENTA, AND HEXACHLOROBENZENES OBSERVED AT THE NIAGARA RIVER DUMP SITES WERE 25%, 100%, 45%, AND 25%, RESPECTIVELY. IN THE NIAGARA BASIN OF LAKE ONTARIO, THE CORRESPONDING PROPORTIONS WERE 72%, 100%, 48%, AND 126% (NORMALIZED TO TETRACHLOROBENZENE FOR COMPARISON). /TETRACHLOROBENZENE/

URBAN/SUBURBAN: 1,2,4,5-Tetrachlorobenzene was detected in the air of Hamburg, Germany at concns of 0.5-20.9 ng/cu m(1). Combined tetrachlorobenzene isomers were detected at mean concns of 690 parts per trillion in the urban air of the US and 95 parts per trillion in source dominated air(2). 1,2,4,5-Tetrachlorobenzene was detected in suburban air in MI at concns of 22-30 pg/cu m(3). The overall mean concn of tetrachlorobenzene isomers in 3 US locations was 3,502 ng/cu m with mean concns of 198 ng/cu m in urban-remote areas, 6,196 ng/cu m in urban areas and 853 ng/cu m in source dominated areas(4). Combined tetrachlorobenzene isomers were detected at concns of trace levels to 300 ng/cu m in the air of Love Canal, NY(5).

Toxicity

moderately toxic

1,2,4,5-Tetrachlorobenzene (TCB) was tested for its effects on fertility & reproduction in Swiss CD-1 mice using the continuous breeding protocol. Male & female mice (F0) were continuously exposed for a 7 day precohabitation & a 98 day cohabitation period (Task 2) to TCB at levels of 0.028, 0.072, & 0.18% /weight/volume/ in the diet. TCB treatment at 0.18% was significantly more toxic than anticipated. Nineteen of the 20 high-dose females died (or were humanely sacrificed) & almost all of these deaths occurred at parturition. None of the males died. In the 0.072% group, a 9% (significant) decr in the number of live pups/litter was noted; no changes were observed in pup weights, proportion of male pups, or days to deliver each litter. Task 3, the determination of the affected sex, was not conducted, given the small change in litter size. At terminal sacrifice, the avg liver weight & the liver-to-body weight ratio in F0 males exposed to 0.18% TCB were almost twice the control values. In the F1 generation, liver & kidneys were enlarged in both sexes exposed to 0.072% TCB. Sperm abnormalities were greater in the 0.18% TCB group by 40%, compared to controls. Seminal vesicle weight was increased in the high-dose-treated males. The second generation was reared consuming control diet, or diet with 0.072% TCB. At sexual maturity, there was no difference in mating, litter size, pup weight (absolute or adjusted), or dam weight. At F1 necropsy, there was an incr in the absolute & relative weights of liver, kidneys, & testis in the 0.072% TCB group, with similar increases in female liver & kidneys weights. There was no change in F1 female estrual cycle parameters. TCB, under the present experimental conditions, exerted mild reproductive toxicity in the presence of considerable systemic toxicity. Thus, TCB is a reproductive toxicant in the presence of significant systemic toxicity.

... Certain medical conditions /skin, liver, kidney, & chronic respiratory disease/ ... might place the employee at increased risk from chlorobenzene exposure. /Chlorobenzene/

The Interagency Testing Committee (ITC) cited several possible sources of contamination /of air, water, soil, and food chains by chlorinated benzenes/ which include the use of chlorinated benzenes as chemical intermediates, as solvents in the manufacture of dyes, as lubricants and pesticides, and as transformer oils. /Chlorinated benzenes/|1,2,4,5-Tetrachlorobenzene's /former/ production and use as an insecticide and intermediate in the production of herbicides and defoliants may have resulted in its release to the environment through various waste streams(1,SRC).|1,2,4,5-Tetrachlorobenzene is a degradation byproduct of pentachlorobenzene and hexachlorobenzene and therefore may enter the environment as a result of the microbial degradation of these compounds(1,SRC).

TERRESTRIAL FATE: Based on a recommended classification scheme(1), and log Koc values in the range of 3.2-3.9(2-4), 1,2,4,5-tetrachlorobenzene is expected to have low mobility in soil(SRC). Volatilization of 1,2,4,5-tetrachlorobenzene is expected from moist soil surfaces(SRC) given its Henry's Law constant of 1.0X10-3 atm-cu m/mole at 20 °C(5), but adsorption may attenuate this process(SRC). Volatilization of 1,2,4,5-tetrachlorobenzene from dry soil surfaces is not expected(SRC) based on a vapor pressure of 0.005 mm Hg at 25 °C(5). Biodegradation is expected to occur slowly based on a half-life of 47 days in a sewage sludge ammended soil(6).|AQUATIC FATE: Based on a recommended classification scheme(1), and log Koc values in the range of 3.2-3.9(2-4), 1,2,4,5-tetrachlorobenzene is expected to adsorb to suspended solids and sediments in water(SRC). 1,2,4,5-Tetrachlorobenzene is expected to volatilize from water surfaces(5,SRC) given its Henry's Law constant of 1.0X10-3 atm-cu m/mole at 20 °C(6), but adsorption may attenuate this process(SRC). Estimated volatilization half-lives for a model river and model lake are 6 and 150 hours, respectively when neglecting adsorption(5,SRC). The volatilization half-life in a model pond is approximately 34 days when adsorption is considered(7). According to a classification scheme(8), BCF values in the range of 1,600 to 4,800, measured in carp(9) and log BCF values of 3.7-4.1 measured in trout(10), suggest that bioconcentration in aquatic organisms is high(SRC). Biodegradation is expected to occur slowly based on a half-life of 29 days measured in anaerobic river sediment(11). When irradiated with light greater than 285 nm, this compound was degraded 61 percent in a water solution in 16 hrs(12), suggesting that photolysis in surface waters may be important(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,2,4,5-tetrachlorobenzene, which has a vapor pressure of 0.005 mm Hg at 25 °C(2), is expected to exist in the vapor phase in the ambient atmosphere. Vapor-phase 1,2,4,5-tetrachlorobenzene 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 200 days(SRC) from its estimated rate constant of 8.2X10-14 cu cm/mole-sec(3).

The rate constant for the vapor-phase reaction of 1,2,4,5-tetrachlorobenzene with photochemically-produced hydroxyl radicals has been estimated as 8.2X10-14 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 200 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). 1,2,4,5-Tetrachlorobenzene is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(SRC). 1,2,4,5-Tetrachlorobenzene in a water solution irradiated at wavelengths greater than 285 nm was 61 percent degraded in 16 hours(2).

2.75e+03|Bioconcentration factor predicted from water solubility= 225 (calculated). /From table/|BCF values of 2,700 to 4,800 were calculated in carp exposed to 10 ug/l of 1,2,4,5-tetrachlorobenzene during a 6 week incubation period and BCF values of 1,600 to 3,900 were measured in carp exposed to 1 ug/l of 1,2,4,5-tetrachlorobenzene during a 6 week incubation period(1). Mean log BCF values of 3.7-4.1 were calculated for rainbow trout exposed to 1,2,4,5-tetrachlorobenzene(2). Mean BCF values of 4,500 and 4,900 were calculated in fish exposed to 1,2,4,5-tetrachlorobenzene in flowing water and static aquaria(3). According to a classification scheme(4), these BCF values suggest that bioconcentration in aquatic organisms is high(SRC).

1.26e+04 L/kg|Koc= 1600 (calculated). /From table/|Log Koc values of 3.9(1) and 3.2(2) were observed for 1,2,4,5-tetrachlorobenzene. A log Koc value of 3.9 was measured for 1,2,4,5-tetrachlorobenzene in sediment obtained from Ise Bay, Japan(3). According to a recommended classification scheme(4), these Koc values suggest that 1,2,4,5-tetrachlorobenzene has low mobility in soil(SRC).

The Henry's Law constant for 1,2,4,5-tetrachlorobenzene is 1.0X10-3 atm-cu m/mole at 20 °C(1). This value indicates that 1,2,4,5-tetrachlorobenzene will volatilize from water(2,SRC), but adsorption may attenuate this process(SRC). 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 approximately 6 hours(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 approximately 150 hours(SRC). The volatilization half-life in a model pond is approximately 34 days when adsorption is considered(3). 1,2,4,5-Tetrachlorobenzene's Henry's Law constant(1) indicates that volatilization from moist soil surfaces is expected, but adsorption may attenuate(SRC). 1,2,4,5-Tetrachlorobenzene is not expected to volatilize from dry soil surfaces(SRC) based on a vapor pressure of 0.005 mm Hg at 25 °C(1).

DRINKING WATER: Combined isomers of tetrachlorobenzene were detected in the drinking water of homes near Love Canal, NY at concns of 120-2,000 ng/l(1). 1,2,4,5-Tetrachlorobenzene was detected in drinking water from 3 Canadian cities near Lake Ontario, with a mean concn of 0.2 ng/l (2).|SURFACE WATER: A mean concentration of 0.1 ng/l was reported at 5 stations on Lake Ontario, but 1,2,4,5-tetrachlorobenzene was not detected in Lake Huron or the Grand River(1). Concentrations of 0.63-6.9 ng/l (mean concn 1.6 ng/l) were detected in Niagara River water between Sept. 1981 and March 1983(2). Levels of 0.39-9.3 ng/l (mean concn 2.0 ng/l) were found in the Niagara River at Niagara-on-the Lake(3). Unidentified isomers of tetrachlorobenzene were detected at levels of 25-200 ppm in water samples taken from sites near two hazardous waste disposal areas in Niagara Falls, NY(4). 1,2,4,5-Tetrachlorobenzene was identified, not quantified, in water/sediment samples from Love Canal, NY(5). Concn of 25 ng/l found in the Rhine River in Germany in 1977(6). Concentrations ranging from approximately 1 to 100 ng/l were detected in the Rhine River in July 1976(7).|SURFACE WATER: Tetrachlorobenzenes (1,2,4,5- and/or 1,2,3,5-tetrachlorobenzene) have been found in water from 9 of 14 stations in Lake Ontario sampled in Oct 1983. The concn found at positive stations ranged from 0.009-0.322 ng/l and the avg of positives was 0.064 ng/l(1).|SURFACE WATER: 1,2,4,5-Tetrachlorobenzene was reported at a mean concn of 0.1 parts per trillion in Lake Ontario(1). 1,2,4,5-Tetrachlorobenzene was detected at concns of 0.39-9.3 ng/l in the Niagara River(2). Water collected in the vicinity of an industrial outfall in the Calacasieu River, LA contained 1,2,3,5- and 1,2,4,5-tetrachlorobenzene at a concn of 42 ng/l(3). Combined isomers of tri- and tetrachlorobenzene were reported in rivers from Slovenia at a mean concn of 80 ng/l(4) and combined isomers of 1,2,3,5- and 1,2,4,5-tetrachlorobenzene were detected at 0.04 ug/l in the Forth Estuary, England(5). 1,2,4,5-Tetrachlorobenzene was detected at concns of 0.048, 0.053 and 0.057 ng/l in Lake Ontario(6). 1,2,4,5-Tetrachlorobenzene was reported at an avg concn of 73 pg/l in Lake Ontario(7). 1,2,4,5-Tetrachlorobenzene was detected in the Elbe River, Germany at concns of 0.2-1.6 ng/l(8). 1,2,4,5-Tetrachlorobenzene was reported at mean concns of 0.02 ng/l (Edwards Point) and 0.04 ng/l (Port Lambton) in Ontario, Canada(9).

1,2,4,5-Tetrachlorobenzene was detected in potatoes (0.486 and 2.19 mg/kg) and lettuce (0.012 mg/kg)(1). Combined 1,2,3,5- and 1,2,4,5-tetrachlorobenzene were detected in the following oils: corn (0.04 mg/kg), rape (0.005 mg/kg), sunflower (0.001 mg/kg), peanut (0.001 mg/kg), sesame (0.005 mg/kg) walnut (0.005 mg/kg), hazelnut (0.01 mg/kg) and poppy (0.005 mg/kg)(2). 1,2,4,5-Tetrachlorobenzene was detected in meat from Yugoslavia at a concn of 1.8 ng/g(3).

1,2,4,5-Tetrachlorobenzene was detected in human milk at a concn of 2 ug/kg(1).

Occupational exposure to 1,2,4,5-tetrachlorobenzene may be through inhalation and dermal contact with this compound at workplaces where this compound is produced or used. The general population may be exposed to 1,2,4,5-tetrachlorobenzene via inhalation of ambient air, ingestion of food and drinking water. (SRC)

Unidentified tetrachlorobenzene isomer(s) were found in human blood samples taken from a resident in the area of the Love Canal at a concentration of 2.6 ng/ml(1). Concentrations of 0.008 to 0.039 ug/g 1,2,4,5-tetrachlorobenzene were detected in human adipose tissue in Japan(2). Mean concentrations of 0.016 ug/g were detected in Yugoslavian human adipose tissue and 2 ug/kg in human milk, respectively(3).|Combined trichlorobenzene and tetrachlorobenzene isomers were detected in human adipose tissue in Slovenia at a concn of 60 ng/g and in human hair samples at 40 ng/g(1). 1,2,4,5-Tetrachlorobenzene was identified, not quantified, in the adipose tissue of non-occupationally exposed individuals in Germany(2).

Drug Information

1,2,4,5-TETRACHLOROBENZENE ACCUM IN ADIPOSE TISSUE FOLLOWING CONTINUOUS ADMIN WITH FOOD TO RATS.|AT END OF 2 YR EXPOSURE AT 5 MG/KG/DAY IN DIET OF DOGS, 1,2,4,5-TETRACHLOROBENZENE REACHED 98 & 97% OF CALCULATED STEADY STATE CONCN IN FAT & PLASMA. IT WAS ELIMINATED FROM FAT & PLASMA WITH HALF-LIFE OF 111 & 104 DAYS. RATE OF ELIMINATION RESULTED IN DRAMATIC CHANGES IN FAT/PLASMA RATIO.|Three tetrachlorobenzene (TCB) congeners (1,2,3,4-, 1,2,3,5-, and 1,2,4,5-tetrachlorobenzene) were administered daily by gavage to pregnant Sprague-Dawley rats at levels of 50, 100, or 200 mg/kg from day 6-15 of gestation. Residues of all three congeners were found in maternal and fetal tissues but generally the amounts of the 1,2,4,5- isomer were about 100 times higher than the other two.|... This study was designed to determine the subchronic toxicity of the tetrachlorobenzenes. Results indicated that 1,2,4,5-tetrachlorobenzene accumulated in fat and liver in a dose dependent manner.|THE MEAN LEVELS OF CHLOROBENZENES (INCLUDING 1,2,4,5-TETRACHLOROBENZENE) IN HUMAN MILK AND ADIPOSE TISSUE WERE DETERMINED AND RANGED FROM TRACES TO 25 UG/KG FOR HUMAN MILK AND FROM NOT DETECTED TO 146 UG/KG FOR ADIPOSE TISSUE. THE DISTRIBUTION OF DIFFERENT CHLOROBENZENE ISOMERS IN ADIPOSE TISSUE AND MILK WAS DIFFERENT.

... /IN URINE FROM RATS DOSED/ WITH TOTAL OF 300 MG/KG OF HEXACHLOROBENZENE FOR 10 MONTHS ... 1,2,4,5-TETRACHLOROBENZENE & CERTAIN OTHER CHLOROBENZENES WERE DETECTED, BUT NOT COMPLETELY IDENTIFIED.|ORAL ADMIN OF 100 MG/KG HEXACHLOROBENZENE TO RATS TWICE/WK PRODUCED 1,2,3,4-TETRACHLOROBENZENE IN URINE & 1,2,4,5-TETRACHLOROBENZENE IN FECES.|1,2,4,5-TETRACHLOROBENZENE IS METABOLIZED TO 2,3,5,6-TETRACHLOROPHENOL IN RABBITS. /FROM TABLE/|Lindane administered to hen pheasants resulted in tetrachlorobenzene being identified ... as part of the array of metabolites found in eggs and chicks as well as in the body tissues of hens. /Tetrachlorobenzenes/|For more Metabolism/Metabolites (Complete) data for 1,2,4,5-TETRACHLOROBENZENE (8 total), please visit the HSDB record page.

61.66 Days|AT END OF 2 YR EXPOSURE AT 5 MG/KG/DAY IN DIET OF DOGS, 1,2,4,5-TETRACHLOROBENZENE WAS ELIMINATED FROM FAT & PLASMA WITH HALF-LIFE OF 111 & 104 DAYS.

SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes, mucous membranes and upper respiratory tract. ACUTE/CHRONIC HAZARDS: This chemical is harmful by inhalation, ingestion or skin absorption. It is an irritant of the skin, eyes, mucous membranes and upper respiratory tract. When heated to decomposition it emits highly toxic fumes of chlorides, carbon monoxide, carbon dioxide and hydrogen chloride gas. (NTP, 1992)

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. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. 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: DO NOT INDUCE VOMITING. 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. Be prepared to transport the victim to a hospital if advised by a physician. 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)


Fresh air, rest. Refer for medical attention.


Remove contaminated clothes. Rinse skin with plenty of water or shower.


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 pulmonary edema and treat if necessary ... . Monitor for shock 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 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 unconscious or in respiratory arrest. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with lactated Ringer's to maintain hydration and adequate urine flow. Watch for signs of fluid overload and pulmonary edema. Consider drug therapy for pulmonary edema ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aromatic hydrocarbons and related compounds/

WORKERS PRODUCING 1,2,4,5-TETRACHLOROBENZENE SHOWED A CLUSTER OF CHROMOSOMAL ABERRATIONS. NO APPRECIABLE INCREASE WAS FOUND IN THE LINDANE WORKERS; CHROMATID-TYPE ABERATIONS WERE MODERATELY INCREASED IN WORKERS IN THE BASUDIN E (DIAZINON) AND THE SAFIDON 40 WP (PHOSMET) GROUPS; STABLE CHROMOSOME-TYPE ABERRATIONS WERE OBSERVED IN THE DITRIFON 50 (TRICHLOROFON) AND THE BASUDIN E GROUPS.

1,2,4,5-tetrachlorobenzene

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion.

Cough.

1,2,4,5-Tetrachlorobenzene Use and Manufacturing

Methods of Manufacturing

... MANUFACTURED ... /BY/ THE CHLORINATION OF BENZENE WITH 4 MOLES OF CHLORINE ...|Iodine plus antimony trichloride is effective in selectively chlorinating 1,2,4-trichlorobenzene to 1,2,4,5-tetrachlorobenzene.

Uses

Used in organic synthesis and pesticide intermediates, flame retardants, etc.

TECHNICAL GRADE /HEXACHLOROBENZENE/ USED IN AGRIC CONTAINS 98% HEXACHLOROBENZENE, 1.8% PENTACHLOROBENZENE, & 0.2% 1,2,4,5-TETRACHLOROBENZENE. /HEXACHLOROBENZENE/

Benzene, 1,2,4,5-tetrachloro-: ACTIVE|S - indicates a substance that is identified in a final Significant New Use Rule.|Distillation range: 240-246 °C

NIOSH 5517-2: Analyte: 1,2,4,5-tetrachlorobenzene; Matrix: air; Technique: gas chromatography, (63)-Ni electron capture detector; Desorption: 2 ml hexane; 30 min ultrasonic agitation; Injection vol: 2 ul; Temp: injection: 220 °C; detector: 300 °C; column: 160 °C; Gases carrier: nitrogen, 30 ml/min, purge: nitrogen, 90 ml/min; Column: 2.0 m X 2 mm ID nickel, 10% Carbowax 20M-TPA on 80/100 mesh Chromosorb W AW; Calibration: standard soln of analytes in hexane; Range: 0.02 to 500 ug/sample; Precision (relative standard deviation): 0.042; Estimated limit of detection: 0.001 ug/ml in hexane; Interferences: Using chromatographic conditions given above, 1,2,3,5-tetrachlorobenzene coelutes with 1,2,4,5-tetrachlorobenzene.|Air Samples ... an air sampling tube packed with two sections of Amberlite XAD-2 resin separated by a silanized glass wool plug, to collect the chlorobenzenes /is used/. The adsorbent is desorbed with carbon tetrachloride and analyzed by gas chromatography using a photoionization detector. When using this method the minimum detection limits for mono, di, tri, tetra and pentachlorobenzenes is 15, 20, 30, 35, and 45 ppb (v/v), respectively. /Chlorobenzenes/|HIGH RESOLUTION GAS CHROMATOGRAPHY OF CHLORINATED BENZENES WAS STUDIED. SATISFACTORY RESOLUTION OF 12 BENZENES, INCLUDING 1,2,4,5-TETRACHLOROBENZENE, WAS OBTAINED.|Negative ion chemical ionization mass spectrometry is evaluated as a method for qualitative and quantitative determination of polyhalogenated aromatic hydrocarbons, including 1,2,4,5-tetrachlorobenzene. Each cmpd or mixture of cmpd is analyzed by glass capillary gas chromatography-mass spectrometry by using different modes of chemical ionization in the mass spectrometer.|For more Analytic Laboratory Methods (Complete) data for 1,2,4,5-TETRACHLOROBENZENE (9 total), please visit the HSDB record page.

CHLOROBENZENES (INDUSTRIAL PRODUCTS), MONOCHLOROBENZENE THROUGH HEXACHLOROBENZENE, @ PPB LEVELS IN HUMAN URINE & BLOOD SAMPLES WERE DETERMINED BY GAS CHROMATOGRAPHY WITH PHOTOIONIZATION DETECTION.|THE MEAN LEVELS OF CHLOROBENZENES (INCLUDING 1,2,4,5-TETRACHLOROBENZENE) IN HUMAN MILK AND ADIPOSE TISSUE WERE DETERMINED BY GLASS CAPILLARY GAS CHROMATOGRAPHY AND RANGED FROM TRACES TO 25 UG/KG FOR HUMAN MILK AND FROM NOT DETECTED TO 146 UG/KG FOR ADIPOSE TISSUE.|RESIDUES OF POLYCHLORINATED COMPOUNDS INCLUDING 1,2,4,5-TETRACHLOROBENZENE HAVE BEEN QUANTITATED BY MULTIPLE-ION-DETECTION GAS CHROMATOGRAPHY-MASS SPECTROMETRY IN GREAT LAKES FISH COLLECTED BETWEEN 1974 AND 1980.

Analysis Methods

Name Column Shape Active Phase(℃) Retention index Temperature Control Method Comments Reference
Kovats' RI, non-polar column, isothermal Capillary SE-30 1347.0 160. isothermal   Santiuste, J.M.Harangi, J.Takács, J.M.Mosaic increments for predicting the gas chromatographic retention data of the chlorobenzenesJ. Chromatogr. A2003, 1002, 1-2, 155-168.
Kovats' RI, non-polar column, isothermal Capillary HP-5 1346.9 120. isothermal   Santiuste, J.M.Harangi, J.Takács, J.M.Mosaic increments for predicting the gas chromatographic retention data of the chlorobenzenesJ. Chromatogr. A2003, 1002, 1-2, 155-168.
Kovats' RI, non-polar column, isothermal Capillary HP-5 1342.6 120. isothermal 60. m/0.25 mm/0.25 μm, N2 Santiuste J.M.Takacs J.M.Relationships between retention data of benzene and chlorobenzenes with their physico-chemical properties and topological indicesChromatographia2003, 58, 87-96.
Kovats' RI, non-polar column, isothermal Capillary HP-5 1357.2 140. isothermal 60. m/0.25 mm/0.25 μm, N2 Santiuste J.M.Takacs J.M.Relationships between retention data of benzene and chlorobenzenes with their physico-chemical properties and topological indicesChromatographia2003, 58, 87-96.
Kovats' RI, non-polar column, isothermal Capillary SPB-1 1328. 140. isothermal 30. m/0.32 mm/0.25 μm Vezzani, S.Bertocchi, A.Moretti, P.Castello, G.Prediction of the gas chromatographic retention values of chlorobenzenes on different station phases by using structure-retention correlationsJ. Chromatogr. A1998, 803, 1-2, 211-218.

Computed Properties

Molecular Weight:215.9
XLogP3:4.6
Exact Mass:215.888111
Monoisotopic Mass:213.891061
Heavy Atom Count:10
Complexity:90.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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