2,3,4,5-Tetrachlorophenol

231.89

231.89

225-531-7

D2UW5NHW9J

2020

DTXSID0022220

Needles from petroleum ether (sublimes)

20.2

4.21

2,3,4,5-tetrachlorophenol appears as needles (from petroleum ether, ligroin) or beige solid. (NTP, 1992)

1.6 at 140° F (NTP, 1992)

116.5 °C

Sublimes

4 °C

1.621

Very soluble in ethanol

APPROX 4°C

pKa=6.35

Insoluble in water.

Phenols and Cresols

2,3,4,5-TETRACHLOROPHENOL is incompatible with acid chlorides, acid anhydrides and oxidizing agents (NTP, 1992).

UN12303/PG2

3

23/24/25-39/23/24/25-67-65-50/53-38-11-41-37/38-25

36/37-45-62-61-60-33-29-16-36/39-26-25

SM9200000

T,N,Xn,F

P210-P260-P280-P301 + P310 + P330-P308 + P311-P403 + P233

H225-H301 + H311 + H331-H370

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number F027, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste. /Tetrachlorophenol/

Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P273, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P362, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 42 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol 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 store this chemical under ambient temperatures, and keep it away from oxidizing materials. (NTP, 1992)

MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves. 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)|The following equipment should be available /in work area/: eyewash, quick drench. /Pentachlorophenol/|If any possibility of eye contact, eye protective equipment should be worn. /Pentachlorophenol/|Recommendations for respirator selection. Max concn for use: 5 mg/cu m: Respirator Classes: Any chemical cartridge respirator with organic vapor cartridge(s) in combination with a dust, mist, and fume filter; may require eye protection. Any supplied-air respirator; may require eye protection. Any self-contained breathing apparatus; may require eye protection. /Pentachlorophenol/|Recommendations for respirator selection. Max concn for use: 12.5 mg/cu m: Respirator Classes: Any supplied-air respirator operated in a continuous flow mode; may require eye protection. Any powered, air-purifying respirator with organic vapor cartridge(s) in combination with a dust, mist, and fume filter; may require eye protection. /Pentachlorophenol/|For more Personal Protective Equipment (PPE) (Complete) data for 2,3,4,5-TETRACHLOROPHENOL (8 total), please visit the HSDB record page.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.|Avoid breathing vapors. Keep upwind. Wear boots, protective gloves, and goggles. Wash away any material which may have contacted the body with copious amounts of water or soap and water. /Pentachlorophenol/|Wear appropriate equipment to prevent: Any possibility of skin contact. /Pentachlorophenol/|Wear eye protection to prevent: Any possibility of eye contact. /Pentachlorophenol/|For more Preventive Measures (Complete) data for 2,3,4,5-TETRACHLOROPHENOL (8 total), please visit the HSDB record page.

/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Health: TOXIC; inhalation, ingestion, or skin contact with material may cause severe injury or death. 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. /Chlorophenols, liquid; Chlorophenols, solid/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors, and sewers explosion hazards. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. /Chlorophenols, liquid; Chlorophenols, solid/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (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. Ventilate enclosed areas. /Chlorophenols, liquid; Chlorophenols, solid/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (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. /Chlorophenols, liquid; Chlorophenols, solid/|For more DOT Emergency Guidelines (Complete) data for 2,3,4,5-TETRACHLOROPHENOL (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.

/Tetrachlorophenol/ dust has been found irritating to the nose and throat ... . /Tetrachlorophenol/|All chlorophenol ... dusts are ... irritating to the respiratory tract. /Chlorophenols/

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. Chlorophenols is produced, as an intermediate or final product, by process units covered under this subpart. /Chlorophenols/

F027; A hazardous waste from nonspecific sources when a component of a discarded unused formulation. /Tetrachlorophenol/

F027; Discarded unused formulations containing tri-, tetra-, or pentachlorophenol or discarded unused formulations containing compounds derived from these chlorophenols are classified as a hazardous waste from a nonspecific source and must be managed according to Federal and/or State hazardous waste regulations. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (see 40 CFR 261.5).

2,3,4,5-Tetrachlorophenol was detected in soils collected from three different saw mills in Finland at up to 1 mg/kg fresh soil, possibly as a degradation product from pentachlorophenol(1). Soil collected at an abandoned sawmill site near a wood-preserving facility contained 2,3,4,5-tetrachlorophenol at 2500 ug/kg dry soil(4). 2,3,4,5-Tetrachlorophenol was measured in the raw gas, upstream from the electrostatic precipitator, from a hazardous waste incinerator at 6.5 to 50 ng/cu m(2). 2,3,4,5-Tetrachlorophenol was reported in the emissions from a metal reclamation plant in Finland(3). Emissions during aluminum smelting (1.2 ug/normalized cu m), car shredding (0.4 ug/normalized cu m), turnings drying (3.7 ug/normalized cu m), sink and float separation (0.0 ug/normalized cu m), and ring crushing (0.1 ug/normalized cu m) were monitored(3). 1 of 40 potable water treatment plants monitored in Canada during October-December 1984 contained 2,3,4,5-tetrachlorophenol at maximum and mean concns of 13 and 0.3 ng/l, respectively, in raw water samples; during February-March 1985, raw water at 1 of 40 plants contained 2,3,4,5-tetrachlorophenol at maximum and mean concns of 12 and 0.2 ng/l, respectively(5). 2,3,4,5-Tetrachlorophenol was not detected at any time in the treated water(5). Twelve sewage sludges from rural, urban and industrial sewage treatment works in NW England contained 2,3,4,5-tetrachlorophenol at 0.04 to 1.36 ug/l with a mean of 0.50 ug/l, wet weight concns(6).

Sediments which were located at the end of a wastewater pipe were monitored for the presence of 2,3,4,5-tetrachlorophenol; concns ranged from 122 to greater than or equal to 400 nmol/kg (dry weight basis)(1). A reference sample taken from a location 250 m from the discharge point contained 2,3,4,5-tetrachlorophenol at less than or equal to 5 nmol/kg (dry weight basis)(1). Concns of 2,3,4,5-tetrachlorophenol ranged from <0.001 to 0.072 ug/g dry weight in the sediment of Pyhaoja Brook, Finland; this stream has been apparently affected by the operation of a sawmill(2). 100% of the sediment samples collected from Lake Ketelmeer contained 2,3,4,5-tetrachlorophenol at a maximum and median concn of 8.9 and 0.9 ug/kg (dry weight basis), respectively(3). Sediment from Haringvliet, Western Scheldt, the Ghent-Terneuzen canal, and the Neuse at Lith (The Netherlands) contained 2,3,4,5-tetrachlorophenol at median concns of 0.9, 0.9, 0.9, and 0.6 ug/kg (dry weight basis), respectively(3).

URBAN/SUBURBAN: Twelve sites in Hamburg, Germany were monitored for air quality over a one year period; 2,3,4,5-tetrachlorophenol had annual mean values for these sites ranging from <0.2(7 sites) to 0.4 ng/cu m(1).

LD50 Mouse oral 400 mg/kg|LD50 Mouse ip 97 mg/kg

2,3,4,5-Tetrachlorophenol can be formed as a product of the biodegradation of pentachlorophenol(1).

TERRESTRIAL FATE: Based on a classification scheme(1), measured Koc values of 13200, 13900, and 12500 for a lake sediment (foc=0.094), river sediment (foc=0.026), and aquifer material (foc=0.0084), respectively(2) indicate that 2,3,4,5-tetrachlorophenol is expected to be immobile in soil(SRC). A pKa of 6.35 indicates that 2,3,4,5-tetrachlorophenol exists mainly as the phenolate anion in neutral and alkaline environments(3). Volatilization of 2,3,4,5-tetrachlorophenol from moist soil surfaces is not expected to be important(SRC) given an estimated Henry's Law constant of 3.5X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(4). 2,3,4,5-Tetrachlorophenol is not expected to volatilize from dry soil surfaces based on an estimated vapor pressure of 1.6X10-4 mm Hg(SRC), determined from a fragment constant method(5). Based on limited data, biodegradation of 2,3,4,5-tetrachlorophenol may occur under both aerobic and anaerobic conditions. 31% and 0% biodegradation of 2,3,4,5-tetrachlorophenol was reported in an aerobic clay loam soil after 160 days and in an anaerobic clay loam soil after 80 days, respectively(6). However, another study using anaerobic estuarine sediment reported a half-life of 6.5 days with the formation of 3,4,5-trichlorophenol (27%) and 2,4,5-trichlorophenol (22%) as major intermediates(7). BCF values of 38 to 41 and 213 to 351 were measured in two species of earthworms, E. fetida andrei and L. rubellus, respectively(8).|AQUATIC FATE: Based on a classification scheme(1), measured Koc values of 13200, 13900, and 12500 for a lake sediment (foc=0.094), river sediment (foc=0.026), and aquifer material (foc=0.0084), respectively(2) indicate that 2,3,4,5-tetrachlorophenol is expected to adsorb to suspended solids and sediment in water(SRC). In a field aqueous adsorption study, the ratio of 2,3,4,5-tetrachlorophenol concn in sediment to water was measured as 680 and in suspended matter to water was 240(3). 2,3,4,5-Tetrachlorophenol is not expected to volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 3.5X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(6), an estimated BCF of 930(5,SRC), from a log Kow value (7), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Photolysis at water surfaces may be an important fate process; a photochemical half-life of 0.88 hours was measured for 2,3,4,5-tetrachlorophenol in a 99% ethanol/1% sodium phosphate solution (pH=7) using filtered light at 295 to 500 nm to simulate sunlight(8). Based on limited data, biodegradation of 2,3,4,5-tetrachlorophenol may occur under both aerobic and anaerobic conditions. In a river die-away study, 2,3,4,5-tetrachlorophenol had a biodegradation rate constant of 1.4X10-7 M/hr; a lag phase of 17 days was reported(9). A study using anaerobic estuarine sediment reported a half-life of 6.5 days with the formation of 3,4,5-trichlorophenol(27%) and 2,4,5-trichlorophenol(22%) as major intermediates(10).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,3,4,5-tetrachlorophenol, which has an estimated vapor pressure of 1.6X10-4 mm Hg at 25 °C(2,SRC), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 2,3,4,5-tetrachlorophenol 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 10 days(3,SRC). Particulate-phase 2,3,4,5-tetrachlorophenol may be physically removed from the air by wet and dry deposition(SRC).

The rate constant for the vapor-phase reaction of 2,3,4,5-tetrachlorophenol with photochemically-produced hydroxyl radicals has been estimated as 1.6X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 10 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1,SRC). 2,3,4,5-tetrachlorophenol is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2). The irradiation of 2,3,4,5-tetrachlorophenol at a wavelength greater than or equal to 285 nm in an acetonitrile-water mixture resulted in 30 and 73% disappearance in 6 and 24 hours, respectively(3). The main photoproduct is 2,3,5-trichlorophenol indicating reductive dechlorination at the para substituent as the process of degradation(3). A photochemical half-life of 0.88 hours was measured for 2,3,4,5-tetrachlorophenol in a 99% ethanol/1% sodium phosphate solution (pH=7); filtered light at 295 to 500 nm was used to simulate sunlight at the maximum intensity of the year in a modified Xenotest 1200 apparatus(4).

An estimated BCF of 930 was calculated for 2,3,4,5-tetrachlorophenol(SRC), using a log Kow value of 4.21(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC). BCF values of 38 to 41 and 213 to 351 were measured in two species of earthworms, E. fetida andrei and L. rubellus, respectively(4). Leeches exposed to water in Thunder Bay Harbor, Lake Superior, Canada for 3 weeks bioaccumulated 2,3,4,5-tetrachlorophenol at 63 to 427 ng/g near wastewater discharge points from a pulp mill; at sites located at a greater distance from the discharge area no bioaccumulation in leeches was seen(5).

1.32e+04 L/kg|The Koc of 2,3,4,5-tetrachlorophenol is estimated as approximately 4600(SRC), using a log Kow value of 4.21(1) and a regression-derived equation(2,SRC). According to a classification scheme(3), this estimated Koc value suggests that 2,3,4,5-tetrachlorophenol is expected to have slight mobility in soil(SRC). Koc values of 13200, 13900, and 12500 were measured for a lake sediment (foc=0.094), river sediment (foc=0.026), and aquifer material (foc=0.0084), respectively(7). A Kp value of 0.94 was measured for 2,3,4,5-tetrachlorophenol in aquifer sand at a pH value of 2(4). 2,3,4,5-Tetrachlorophenol added to Eustis fine sand (0.23-0.39% organic carbon; 96.4% sand) had a measured Kp value of 4.19 mL/g; 47% of this compound was ionized in this experiment(6). In addition, a desorption rate coefficient of 2.07 per hour was measured(6). In an aqueous adsorption study, 1360 pg/g 2,3,4,5-tetrachlorophenol was found in the sediment, 480 pg/g in suspended matter, and 2 pg/g in the water; the sediment to water ratio is 680 and suspended matter to water ratio is 240(5).

The Henry's Law constant for 2,3,4,5-tetrachlorophenol is estimated as 3.5X10-7 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2,3,4,5-tetrachlorophenol is expected to be essentially nonvolatile from water surfaces(2,SRC). 2,3,4,5-Tetrachlorophenol's Henry's Law constant(1,SRC) indicates that volatilization from moist soil surfaces may occur(SRC). 2,3,4,5-Tetrachlorophenol is not expected to volatilize from dry soil surfaces based on an estimated vapor pressure of 1.6X10-4 mm Hg(SRC), determined from a fragment constant method(3).

SURFACE WATER: 8 of 41 water samples collected from Thunder Bay, Lake Superior, Canada contained 2,3,4,5-tetrachlorophenol at concns greater than the detection limit of 50 ng/l(1). Concns of 2,3,4,5-tetrachlorophenol from <0.001 to 0.493 ug/l were measured in Pyhaoja Brook, Finland; the water was apparently affected by a sawmill operation(2). Water samples collected from the Weser River (downstream from Bremen, Germany), in the German Bight (south of Helgoland), and in the German Bight (north of Helgoland) contained 2,3,4,5-tetrachlorophenol at concns of 0.5-2.9 ng/l, 0.04 ng/l, and trace quantities, respectively(3). 2,3,4,5-Tetrachlorophenol was detected in 4% of water samples collected from the Rhine River at Lobith (The Netherlands) in 1976 and 1977 at a maximum concn of 0.14 ppb; this compound was not detected in the Meuse River at Eijsden (The Netherlands) in 1976 and 1977(4). 23% of the surface water samples obtained from the Ijssel River near Kampen (The Netherlands) contained 2,3,4,5-tetrachlorophenol at a maximum concn of 0.02 ug/l(5).

The most probable human exposure would be occupational exposure, which may occur through dermal contact or inhalation at workplaces such as pulp and paper mills or sawmills. (SRC)

2,3,4,5-Tetrachlorophenol has been detected in unreported quantities in adipose tissue and/or milk of non-occupationally exposed humans(1).

The compounds are readily absorbed from the gastroenteric tract and from parenteral sites of injection. /Chlorophenols/|Chlorophenols ... are readily absorbed from all routes including percutaneous and inhalation. /Chlorophenols/

The comparative formation of chlorophenol metabolites of hexachlorocyclohexane was investigated in rats and mice. Male Swiss mice and female Wistar rats were fed a diet containing 500 ppm hexachlorocyclohexane. Circulating concentrations of chlorophenols were determined after 24 hr in Wistar rats and Swiss mice given a single 200 mg/kg ip injection of hexachlorocyclohexane. Chlorophenol metabolites identified included 2,3,4,5-tetrachlorophenol. Species differences in the rate of chlorophenol metabolite formation in vitro were also measured in hepatic microsome fractions prepared from Aroclor 1254 pretreated animals.|The comparative formation of chlorophenol metabolites of hexachlorocyclohexane was investigated in rats and mice. Male Swiss mice and female Wistar rats were fed a diet containing 500 parts per million hexachlorocyclohexane. Animals were killed after 2 months and hepatic chlorophenol metabolites were determined using hig performance liquid chromatography. Circulating concentrations of chlorophenols were determined in Wistar rats and Swiss mice given a single 200 mg/kg intraperitoneal injection of hexachlorocyclohexane. After 24 hours blood was collected by heart puncture and chlorophenols assayed chromatographically. Species differences in the rate of chlorophenol metabolite formation in vitro were also measured in hepatic microsome fractions prepared from Aroclor 1254 pretreated animals. Chlorophenol metabolites identified were 2,6-dichlorophenol, 2,3,5-trichlorophenol, 2,3,6-trichlorophenol, 2,4,6-trichlorophenol, 2,3,4,5-tetrachlorophenol, 2,3,5,6-tetrachlorophenol, and pentachlorophenol. No qualitative species difference was detected in chromatographic profiles of chlorophenols extracted from mouse and rat liver after continuous 2 month administration of hexachlorocyclohexane. Only 2,6-dichlorophenol was significantly higher in mouse live than that observed in rat liver: 1292.5 ng/g in mouse and 140.0 ng/g in rat. No qualitative difference was observed in the chlorophenols of blood of mice and rats. However, the concentration of 2,6-dichlorophenol was 11.52 ug/ml compared to 1.65 ug/ml in mouse blood. In vitro, 647 picomoles/mg/hour 2,4,6-trichlorophenol were formed by rat liver microsomes, compared to 219 picomoles/mg/hour by mouse liver microsomes. It was concluded that hexachlorocyclohexane may be a tumor promoting agent which acts by facilitating the development of latent initiated cells of unknown origin. Differential plasma clearance of 2,6-dichlorophenol may account for species differences in its concentration; however it is unlikely that it plays a major role in the induction of liver tumors in mice.|The metabolism of tetrachlorobenzenes was investigated in the squirrel monkey and a comparison made of the interspecies metabolism of such compounds. Three groups of four male monkeys were given orally single doses of one of three tetrachlorobenzene isomers in corn oil twice per week for 3 weeks. The dose levels for 1,2,3,4-tetrachlorobenzene and 1,2,3,5-tetrachlorobenzene were 100 mg/kg, and the dose level for 1,2,4,5-tetrachlorobenzene was 50 mg/kg. Respective levels of fecal excretion at 48 hours were 38, 36, and 18% of the initial doses. No metabolism occurred for 1,2,4,5-tetrachlorobenzene in the squirrel monkey. Fecal metabolites of 1,2,3,5-tetrachlorobenzene included 2,3,4,5-tetrachlorophenol (2% of dose), 2,3,4,6-tetrachlorophenol (14%), 2,3,5,6-tetrachlorophenol (9%), and 2,3,5,6-tetrachlorophenyl-sulfinic-acid (15%). For animals dosed with either 1,2,3,4-tetrachlorobenzene or 1,2,3,5-tetrachlorobenzene, the fecal radioactivity demonstrated elimination of at least 50% unchanged compound. Fecal metabolites in monkeys dosed with 1,2,3,4-tetrachlorobenzene included 1,2,4,5-tetrachlorophenol (22 %), N-acetyl-S-(2,3,4,5-tetrachlorophenyl)cysteine (18%), 2,3,4,5-tetrachlorophenyl sulfinic acid (3%), 2,3,4-trichlorophenyl-methyl sulfide (0.6%), and 2,3,4,5-tetrachlorophenyl-methyl sulfide (0.2%). Different metabolic pathways were briefly compared for the squirrel monkey, the rat, and the rabbit. The authors conclude that the tetrachlorobenzenes studied are metabolized differently in different species and that different isomers are metabolized by different pathways.

CHLORINATED PHENOLS ... ARE VERY EFFECTIVE ( ... IN VITRO) AS UNCOUPLERS OF OXIDATIVE PHOSPHORYLATION. THEY THUS PREVENT INCORPORATION OF INORGANIC PHOSPHATE INTO ATP WITHOUT EFFECTING ELECTRON TRANSPORT. AS A RESULT OF THIS ACTION, WHICH IS BELIEVED TO OCCUR @ MITOCHONDRIAL /MEMBRANE/, CELLS CONTINUE TO RESPIRE BUT SOON ARE DEPLETED OF ATP NECESSARY FOR GROWTH. /CHLOROPHENOLS/|The chlorophenols ... act at the sites of adenosine triphosphate production and decrease or block it without blocking the electron transport chain. Thus the poisons uncouple phosphorylation from oxidation. Free energy from the electron transport chain then converts to more body heat. As body temp rises, heat-dissipating mechanisms are overcome and metabolism is speeded. More adenosine diphosphate and other substrates accumulate, and these substrates stimulate the electron transport chain further. The electron transport chain responds by using up more and more available oxygen (increasing oxygen demand) in an effort to produce adenosine triphosphate, but much of the free energy generated is liberated as still more body heat. Oxygen demand quickly overcomes oxygen supply, and energy reserves become depleted. /Chlorophenols/

SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes, mucous membranes and upper respiratory tract. Depending on the intensity and duration of exposure, effects may vary from mild irritation to severe destruction of tissue. Prolonged contact can cause eye damage. It can also cause irritation of the nose and throat. Exposure to this type of compound may cause profuse sweating, intense thirst, abdominal pain, nausea, vomiting, diarrhea, cyanosis from methemoglobinemia, hyperactivity, stupor, blood pressure fall, hyperpnea, hemolysis, convulsions, collapse, coma and pulmonary edema followed by pneumonia. If death from respiratory failure is not immediate, jaundice and oliguria or anuria may occur. Other symptoms of exposure to this type of compound may include headache, dizziness, rapid and difficult breathing, weakness, severe burns and internal damage. Chronic exposure may result in digestive disturbances, nervous disorders, skin eruptions and liver and kidney damage. Skin contact with this type of compound may result in softening and whitening of the skin, followed by the development of painful burns. Prolonged contact may lead to dermatitis. Local contact may also result in painless blanching or erythema and corrosion of the skin. Skin sensitivity reactions occur occasionally. ACUTE/CHRONIC HAZARDS: This compound is highly toxic by inhalation, ingestion and skin absorption. It is an irritant of the skin, eyes, mucous membranes and upper respiratory tract; and prolonged contact may result in severe irritation or destruction of tissue. It is also an irritant of the nose and throat. When heated to decomposition it emits toxic fumes of 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. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. Phenols are very toxic poisons AND corrosive and irritating, so that inducing vomiting may make medical problems worse. IMMEDIATELY call a hospital or poison control center and locate activated charcoal, egg whites, or milk in case the medical advisor recommends administering one of them. If advice from a physician is not readily available and the victim is conscious and not convulsing, give the victim a glass of activated charcoal slurry in water or, if this is not available, a glass of milk, or beaten egg whites and IMMEDIATELY transport victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, assure 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)

Chlorophenols appear to be mildly hepatotoxic, and studies in animals indicate that pentachlorophenol may reduce humoral and cell-mediated immunity as well as act as a cocarcinogen. /Chlorophenols/|Solid & 10% aq suspensions are not primary skin irritants, but repeated skin contact may result in acneform dermatitis. ... In eye conjunctivitis & slight-to-moderate corneal injuries are described. Dust may irritate nose & pharynx. Chronic exposure to a mixture of penta- and tetrachlorophenol is reported to have caused aplastic anemia in one adult. /Penta- and tetrachlorphenol/

2,3,4,5-tetrachlorophenate

EPA Method 8040. Method for the determination of phenols in solid waste by gas chromatography with flame ionization detection or derivatization to pentafluorobenzyl- bromide derivatives followed by gas chromatography with electron capture detection. Electron capture detection is used to reduce detection limits of some phenols and/or interferences. Under the prescribed conditions for tetrachlorophenols, the method detection limit is not given for using flame ionization detection and electron capture detection. Precision and method accuracy were found to be directly related to analyte concentration and essentially independent of the sample matrix. /Tetrachlorophenols/|OSW Method 8041. Phenols by Gas Chromatography: Capillary Column Technique. Used to monitor phenols in both water and solids.|HERL Method HERL_006. Pentachlorophenol (PCP) and Chlorinated Phenol Metabolites of PCP and HCB. Analysis by GC/ECD. This method is applicable to the determination of PCP in human and animal urine.

A GC method for determining 2,3,4,6-tetrachlorophenol in biological fluids was developed. Samples analyzed were urine, water, serum, or fish, tissue. Urine and water samples were digested at 100 °C for 1 hr in a sealed vial and later were extracted with toluene. Serum samples were acidified and then digested and extracted as above. Fish tissue was homogenized, acidified to pH 2, and rehomogenized; the emulsion was extracted with methylene chloride, extracted with alkali, and finally with toluene and digested as above. All samples were treated with an internal standard, diluted as appropriate, and subjected to gas chromatography at 300 °C using fused silica capillary columns. Samples were injected at 1 ul volume and detection was facilitated by electron capture at 350 °C. A calibration standard of pure tetrachlorophenol was run; the time of chromatographic run was 1 hr. Good resolution was achieved. Concentrations as low as 0.5 ppb were detected by this method. The precision of the method was 7.5% for tetrachlorophenol. The upper limit of detection was 200 ppb. Samples of water, urine, serum, and fish tissue contained a detectable concentration. Corrections were made to compensate for instrument drift. The compounds were sensitive to chemical activity within the injection port and column; deactivation was necessary by treating with 10 microliter portions of hexamethylsilane and trimethylchlorosilane. This method offers high sensitivity and precision for examining tetrachlorophenol. /Tetrachlorophenol/|Chlorinated phenols in urine are detected by electron-capture gas chromatography using a double support-bonded diethylene glycol succinate column. Avg recoveries of >80% were obtained. /Chlorinated phenols/