2,4,6-트리클로로페놀

Hazardous Air Pollutants (HAPs)

Other Classes -> Chlorophenols

Carcinogens

Chlorinated/Brominated phenol

Semi-Volatile Organic Compound (SVOC)

Pesticide -> EPA IRIS

Environmental transformation -> Pesticide transformation products (metabolite, successor)

log Kow = 3.69

3.7

3.83

1.675 at 77 °F (NTP, 1992) - Denser than water; will sink

1.4901

Density: 1.4901g/cu cm at 75 °C

Density (at 25 °C): 1.7 g/cm³

1.4901 @ 75°C

Crystals from ligroin

Yellow flakes

Orthorhombic needles from acetic acid

less than 0.1 mg/mL at 64 °F (NTP, 1992)

In water, 500 mg/L at 25 °C

525 g/100 g acetone; 113 g/100 g benzene; 37 g/100 g carbon tetrachloride; 335 g/100 g diacetone alcohol; 400 g/100 g denatured alcohol formula; 525 g/100 g methanol; 163 g/100 g pine oil; 16 g/100 g Stoddard solvent; 100 g/100 g toluene; 37 g/100 g turpentine

Soluble in ethanol, ethyl ether, acetic acid

Solubility in water, g/l at 20 °C: 0.8 (very poor)

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P203, P264, P264+P265, P270, P273, P280, P301+P317, P302+P352, P305+P351+P338, P318, P321, P330, P332+P317, P337+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P264, P264+P265, P270, P273, P280, P301+P317, P302+P352, P305+P351+P338, P318, P321, P330, P332+P317, P337+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)

Chemical: Phenol, 2,4,6-trichloro-

Hazard Traits - Carcinogenicity

Regulation (EC) No 1107/2009 (amended)

2,4,6-Trichlorophenol: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Literature sources indicate that this chemical is nonflammable. (NTP, 1992)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes, nose, throat, mucous membranes and upper respiratory tract. Contact with the skin may result in redness, edema, dermatitis and chemical burns. Contact with the eyes may result in corneal injury and iritis. It may also cause lacrimation. Other symptoms may include an increase followed by a decrease in respiratory rate and urinary output, fever, increased bowel action, weakness of movement, collapse, convulsions, lung damage, liver damage and kidney damage. Additional symptoms caused by this type of compound include painless blanching or erythema of the skin, corrosion, profuse sweating, intense thirst, nausea and vomiting, diarrhea, cyanosis from methemoglobinemia, hyperactivity, hyperthermia, skin rashes (sometimes chloracne), neurological and immunological effects, stupor, blood pressure fall, hyperpnea, abdominal pain, hemolysis, coma, and pulmonary edema followed by pneumonia. Rapid death has been reported. If death from respiratory failure is not immediate, jaundice and oliguria or anuria may occur. Skin sensitivity reactions occur occasionally. Prolonged eye contact may cause eye damage. Depending on the intensity and duration of exposure, effects may include severe destruction of tissue.

2,4,6-Trichlorophenol is no longer used in the United States and only very low levels have been detected in ambient air. Limited information is available on the acute (short-term) and chronic (long-term) effects of 2,4,6-trichlorophenol in humans. The only available human study reported respiratory effects, such as cough, chronic bronchitis, chest wheezing, altered pulmonary function, and pulmonary lesions from chronic exposure to 2,4,6-trichlorophenol via inhalation. There are no studies available on the reproductive, developmental, or carcinogenic effects of 2,4,6-trichlorophenol in humans. 2,4,6- Trichlorophenol has been shown to be carcinogenic in animals, producing lymphomas, leukemia, and liver cancer via oral exposure. EPA has classified 2,4,6-trichlorophenol as a Group B2, probable human carcinogen.

A skin, eye, and respiratory tract irritant; May cause liver injury; [ICSC] May cause lacrimation; [HSDB] Acute toxicity resembles that of pentachlorophenol; [CAMEO] An irritant; [MSDSonline] See 2,4-Dichlorophenol and Pentachlorophenol. See CHLOROPHENOLS.

USEPA; Ambient Water Quality Criteria Doc: Chlorinated Phenols (1980) EPA 440/5-80-032

DHHS/ATSDR; Toxicological Profile for 2,4,6-Trichlorophenol (1990) TP-90/28

WHO; Environmental Health Criteria 93; Chlorophenols Other Than Pentachlorophenol (1989)

DHEW/NCI; Bioassay of 2,4,6-Trichlorophenol for Possible Carcinogenicity (1979) Technical Rpt Series No. 155 DHEW Pub No. (NIH) 79-1711

National Toxicology Program. Report on Carcinogens, Thirteenth Edition (2014). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. 2,4,6-Trichlorophenol (88-06-2) is listed as reasonably anticipated to be a human carcinogen.[Available from, as of November 6, 2014: http://ntp.niehs.nih.gov/ntp/roc/content/profiles/trichlorophenol.pdf]

D042; A solid waste containing 2,4,6-trichlorophenol may or may not become characterized as a hazardous waste when subjected to the Toxicity Characteristic Leaching Procedure listed in 40 CFR 261.24, and if so characterized, must be managed as a hazardous waste.

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).

2,4,6-TRICHLOROPHENOL is incompatible with acid chlorides, acid anhydrides and oxidizing agents. It can be converted to the sodium salt by reaction with sodium carbonate. Forms ethers, esters and salts by reaction with metals and amines. Undergoes substitution reactions such as nitration, alkylation, acetylation and halogenation. Can be hydrolyzed by reaction with bases at elevated temperatures and pressures. Reacts with alkalis at high temperatures (NTP, 1992).

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)

Use foam, dry powder, carbon dioxide.

Fresh air, rest.

Remove contaminated clothes. To remove substance use polyethylene glycol 300 or vegetable oil. Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Do NOT induce vomiting. Refer for medical attention .

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.

If material /is/ involved in /a/ fire, extinguish fire using agent suitable for type of surrounding fire. Material itself does not burn or burns with difficulty. /Trichlorophenol/

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/

Conditions for safe storage, including any incompatibilities: Keep container tightly closed in a dry and well-ventilated place.

Activated carbon is a good method for removing chlorophenols from water. Competitive adsorption occurs between chlorophenols & humic substances present in nearly all municipal water supplies. This competition decr the capacity of carbon for chlorophenols. /Chlorophenols/

Land Spill: Dig a pit, pond, lagoon, or 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./ Cover solids with plastic sheet to prevent dissolving in rain or fire fighting water. /Trichlorophenol/

Water Spill: Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. If dissolved, apply activated carbon at ten times the spilled amount in region of 10 ppm or greater concentration. Remove trapped material with suction hoses. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates. /Trichlorophenol/

PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

Accidental Release Measures. Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

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.

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste numbers D042 and F027, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

2,4,6-Trichlorophenol is a potential candidate for rotary kiln incineration, with a temperature range of 820 to 1,600 °C and a residence time of seconds.

Incineration, preferably after mixing with another combustible fuel. Care must be exercised to assure complete combustion to prevent the formation of phosgene. An acid scrubber is necessary to remove the halo acids produced. Recommendable method: Incineration. Not recommendable method: Discharge to sewer.

PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/

For more Disposal Methods (Complete) data for 2,4,6-TRICHLOROPHENOL (13 total), please visit the HSDB record page.

Personal protection: filter respirator for organic gases and particulates adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

Keep material out of water sources and sewers; Build dikes to contain flow as necessary. Keep upwind; Avoid breathing vapors or dusts; Wash away any material which may have contacted the body with copious amounts of water or soap and water. /Trichlorophenol/

Smoking, eating, and drinking before washing should be absolutely prohibited when any pesticide ... is being handled or used. /Pesticides/

PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/

For more Preventive Measures (Complete) data for 2,4,6-TRICHLOROPHENOL (16 total), please visit the HSDB record page.

2,4,6-Trichlorophenol was detected in 8 of 10 human urine samples at 25-200 ppb with an average of 88 ppb(1). Workers in a Finnish sawmill had detectable urinary levels of 2,4,6-trichlorophenol of 1-11.8 umols/L(2). 2,4,6-Trichlorophenol was detected at 1.1, 0.15 and 0.3 ug/g creatinine in the urine of plant, laboratory and administration workers, respectively, of the only hazardous waste incineration plant in Spain in 1999, located in Constanti(3). 2,4,6-Trichlorophenol was not detected (detection limit 0.10 ug/L) in the amniotic fluid collected from 100 pregnant women from the San Joaquin Valley, CA(4).

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.

EC50; Species: Scenedesmus subspicatus (Green Algae); Conditions: freshwater, static; Concentration: 279000 ug/L for 49-79 min; Effect: population, decreased photosynthesis

EC50; Species: Chlorella vulgaris (Green Algae) Exponential Growth Phase, 50000 cells/mL; Conditions: freshwater, static, 21 °C; Concentration: 10000 ug/L for 4 hr; Effect: general growth /formulation/

EC50; Species: Pseudokirchneriella subcapitata (Green Algae) Exponential Growth Phase, 50000 cells/mL; Conditions: freshwater, static, 21 °C; Concentration: 3500 ug/L for 4 hr; Effect: general growth /formulation/

EC50; Species: Daphnia magna (Water Flea) age 0-24 hr; Conditions: freshwater, flow through, 17.2 (16.5-18.4) °C, pH 7.39 (6.84-7.80), hardness 44.7 mg/L CaCO3 (40.8-47.6 mg/L CaCO3), alkalinity 43.0 mg/L CaCO3 (40.4-49.5 mg/L CaCO3), dissolved oxygen 8.7 (4.8-10.7) mg/L ; Concentration: 3340 ug/L for 48 hr (95% confidence interval: 2810-3970 ug/L); Effect: intoxication, immobilization

For more Ecotoxicity Values (Complete) data for 2,4,6-TRICHLOROPHENOL (12 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 150-2200(2-4), indicate that 2,4,6-trichlorophenol is expected to have moderate to slight mobility in soil(SRC). The pKa of 2,4,6-trichlorophenol is 6.23(5), indicating that this compound will exist partially in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(6). Volatilization of the anion form of 2,4,6-trichlorophenol from moist soil surfaces is not expected because anions do not volatilize(SRC). Volatilization of neutral 2,4,6-trichlorophenol from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.2X10-6 atm-cu m/mole(SRC), based upon its vapor pressure, 0.008 mm Hg(7), and water solubility, 500 mg/L(8). 2,4,6-Trichlorophenol is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(7). This compound is expected to biodegrade in soils with aerobic and anaerobic biodegradation half-lives in soils of about 5 and 20 days, respectively(9).

AQUATIC FATE: Based on a classification scheme(1), a Koc values of 150-2200(2-4), indicate that 2,4,6-trichlorophenol is expected to adsorb to suspended solids and sediment(SRC). A pKa of 6.23(5) indicates 2,4,6-trichlorophenol will exist partially in the anion form at pH values of 5 to 9 and, therefore, volatilization of the anion form from water surfaces is not expected to be an important fate process(SRC). Volatilization of the neutral form from water surfaces is expected(6) based upon an estimated Henry's Law constant of 4.2X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 0.008 mm Hg(7), and water solubility, 500 mg/L(8). Using this Henry's Law constant and an estimation method(6), volatilization half-lives for the neutral form from a model river and model lake are 20 and 150 days, respectively(SRC). 2,4,6-Trichlorophenol is expected to undergo photolysis in surface waters based on an aqueous photodegradation half-life of 2.1 hours when irradiated with light at environmentally relevant wavelengths(9). 2,4,6-Trichlorophenol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(6). According to a classification scheme(10), BCFs of 87-676(11-13) in fish, suggest bioconcentration in aquatic organisms is moderate to high(SRC). 2,4,6-Trichlorophenol biodegraded 100% in 8-14 days in filtered and unfiltered water(14).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,4,6-trichlorophenol, which has a vapor pressure of 0.008 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,4,6-trichlorophenol 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 24 days(SRC), calculated from its rate constant of 6.1X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 2,4,6-Trichlorophenol contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). Coated on silica gels and irradiated with light wavelengths >290 nm for 17 hours, 2,4,6-trichlorophenol was degraded 65.8%(5).

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

Oral (L159); inhalation (L159) ; dermal (L159)

IDENTIFICATION AND USE: 2,4,6-Trichlorophenol (2,4,6 -TCP) is a colorless needle or yellow solid that has a strong phenolic odor. This germicidal agent was used as a fungicide, bactericide, wood preservative, biocide, and intermediate in production of higher chlorinated phenols. It is not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses. HUMAN EXPOSURE AND TOXICITY: Trichlorophenols produce redness and edema on skin contact and on prolonged exposure mild to moderate chemical burns of skin of man. In eye they induce conjunctival irritation and sometimes corneal injury and iritis. Dusts are irritating to nose and pharynx and systemic effects presumably resemble phenol. Trichlorophenols can have an irritating effect on the lung, and it cannot be excluded that long-term exposure may produce pulmonary fibrosis. Children with low levels (<3.58 ug/g) and high levels (=3.58 ug/g) of urinary 2,4,6-TCP had a higher risk of parent-reported ADHD compared to children with levels below the limit of detection after adjusting for covariates. It was concluded that exposure to TCP may increase the risk of behavioral impairment in children. The potential neurotoxicity of these chemicals should be considered in public health efforts to reduce environmental exposures/contamination, especially in countries where organochlorine pesticides are still commonly used. 2,4,6-Trichlorophenol is reasonably anticipated to be a human carcinogen according to NTP. ANIMAL STUDIES: In rats lethal doses of chlorophenols produce restlessness, increased rate of respiration, rapidly developing motor weakness, tremors, clonic convulsions, dyspnea, and coma. 2,4,6-TCP produces these signs but decreased activity and motor weakness do not appear quite so promptly. 2,4,6-TCP was not hepatotoxic in rats as assessed by measurement of hepatic glucose-6-phosphatase and serum sorbitol dehydrogenase. Carcinogenesis bioassays were conducted by giving 2,4,6-TCP in feed to groups of male and female rats and male mice for two years. Adverse effects at two years were leukocytosis and monocytosis of peripheral blood and hyperplasia of bone marrow in both sexes of rats. In mice, liver toxicity, including individual liver cell abnormalities, focal areas of cellular alteration, and focal and nodular areas of hyperplasia were commonly present. TCP caused leukemias/lymphomas in male rats, and possibly in female rats and female mice as well, and induced liver tumors in male and female mice. 2,4,6-TCP, a non-mutagen to Salmonella, was negative in tests for chromosome breakage in vitro, but did produce numerical chromosome changes and micronuclei in V79 cells. 2,4,6-TCP induces structural chromosome aberrations in CHO cells and in V79 cells using a 3-hr treatment and 20-hr sampling time (17-hr recovery). Positive results were obtained when a recovery time of 4-12 hr was allowed after the 24-hr treatment with 2,4,6-TCP, and when 2,4,6-TCP was tested with S9. ECOTOXICITY STUDIES: 2,4,6-TCP was applied at single doses of into compartments of a natural experimental pond to study the effect on biota. Changes seen included a rapid decline of daphnia concentration to zero after phytoplankton, a continuous increase of contamination indicators like flagellates and microorganisms, and a significant decrease in O2 concentration as a secondary effect of the changed balance between autotrophic and heterotrophic populations.

2,4,6-Trichlorophenol is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.

/AQUATIC SPECIES/ 2,4,6-trichlorophenol was applied at single doses of 5 mg/L in duplicates into compartments of a natural experimental pond to study the effect on biota. Changes seen included a rapid decline of Daphnia concentration to zero after phytoplankton, a continuous increase of contamination indicators like flagellates and microorganisms, and a significant decrease in O2 concentration as a secondary effect of the changed balance between autotrophic and heterotrophic populations.

/AQUATIC SPECIES/ Rainbow trout were exposed for 4 or 8 days to various types of toxicants, each applied to the test water at a high sublethal concentration. The activity of liver uridine diphosphate-glucuronosyltransferase was assayed from the submitochondrial fraction using p-nitrophenol as an aglycone. Activity of uridine diphosphate-glucuronosyltransferase was inhibited by 2,4,6-trichlorophenol.

/AQUATIC SPECIES/ Correlation was found between acute (24 hr) toxicity (median inhibitory concn IC50) to Daphnia magna of 17 chlorophenols /including 2,4,6-trichlorophenol/ and their octanol water partition coefficients, dissociation constants, melting points, the perimeter of the efficient section of the molecule or molecular connectivity index of the first order. Phenols with chlorine in para-position were more toxic than those with chlorine in ortho-position.

2,4,6-Trichlorophenol was detected in 4 of 23 plankton samples from Finnish lake-river system at an average of 2.45 ppb(1). 2,4,6-Trichlorophenol was not detected (detection limit 0.2 ng/g cork) in cork samples collected Jun 2008 from Extremadura, Castile-La Mancha and Catalonia, Spain and Alentejo, Portugal(2).

2,4,6-Trichlorophenol was detected in pine needle wax from 10-20 year old trees near pollution sources; samples were collected from three areas of Finland in 1991-1996(1).[Table#4708]

D042; A solid waste containing 2,4,6-trichlorophenol may or may not become characterized as a hazardous waste when subjected to the Toxicity Characteristic Leaching Procedure listed in 40 CFR 261.24, and if so characterized, must be managed as a hazardous waste.

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).

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

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. 2,4,6-Trichlorophenol is included on this list.

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 10 lb or 4.54 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

Toxic pollutant designated pursuant to section 307(a)(1) of the Federal Water Pollution Control Act and is subject to effluent limitations. /Chlorinated phenols/

2,4,6-Trichlorophenol is designated as a hazardous substance under section 311(b)(2)(A) of the Federal Water Pollution Control Act and further regulated by the Clean Water Act Amendments of 1977 and 1978. These regulations apply to discharges of this substance. This designation includes any isomers and hydrates, as well as any solutions and mixtures containing this substance.

The levels which may result in incremental increase of cancer risk over the lifetime are estimated at 10-5, 10-6, and 10-7. The corresponding criteria are 12 ug/L, 1.2 ug/L, and 0.12 ug/L, respectively.

(AZ) ARIZONA 1.8 ug/L

(FL) FLORIDA 10 ug/L

(ME) MAINE 32 ug/L

(MN) MINNESOTA 30 ug/L

For more State Drinking Water Guidelines (Complete) data for 2,4,6-TRICHLOROPHENOL (6 total), please visit the HSDB record page.

It has been suggested that the mechanism of action of 2,4,6-trichlorophenol is interference with mitochondrial oxidative phosphorylation and inhibition of cytochrome p450-dependent mixed-function oxidases.

Pentachlorophenol, uncoupler of mitochondrial oxidative phosphorylation, disturbed rat liver microsomal detoxification functions by inhibition of terminal oxygenation enzyme p450. Lower concn gave shift in detoxification of aromatic amines from C- to N-oxygenatioN. 2,4,6-T is similar.

The induction of forward mutation to 6-thioguanine resistance in V79 Chinese hamster cells by six different chlorophenols was examined. Chlorophenols examined in this study included: pentachlorophenol, 2,4-dichlorophenol, 2,6-dichlorophenol, 2,4,5-trichlorophenol, 2,4,6-trichlorophenol, and 2,3,4,6-tetrachlorophenol. Cells were plated in 9 mL of medium and cultured for 24 hours. The test chemical was added to the dishes in 1 mL of medium to give the desired concentration. The following dose ranges were tested: 2,4-dichlorophenol, 12.5 to 50 ug/mL; 2,6-dichlorophenol, 125 to 500 ug/mL; 2,4,5-trichlorophenol, 6.25 to 50 ug/mL; 2,4,6-trichlorophenol, 12.5 to 100 ug/mL; 2,3,4,6-tetrachlorophenol, 12.5 to 100 ug/mL; pentachlorophenol, 6.25 to 50 ug/mL. Each of the chlorophenols tested reduced the plating efficiency in a dose dependent manner. This cytotoxic effect can be attributed to the ability of pentachlorophenol and other chlorophenols to inhibit oxidative phosphorylation. None of the chlorophenols produced significant increases in the frequency of 6-thioguanine resistant mutants. However, the apparent lack of induction of gene mutation by chorophenols does not necessarily mean the lack of genotoxicity of these chemicals.

The concentration of 2,4,6-trichlorophenol was measured in the blood and various other tissues of the rat after ip administration of the compound at 25 mg/kg body weight. The highest concentration, 329 + or - 117 nmol per gram of tissue/, was found in the kidney. Half-times were between 1.4 and 1.8 hr in the blood, brain, fat, kidney, liver and muscle.

When chlorophenols are eaten, almost all of the compounds quickly enter the body. Chlorophenols also rapidly enter the body through the skin. Little is known about how much of the chlorophenols enter the body if one breathes air containing them... The other chlorophenols (dichlorophenol, trichlorophenols, tetrachlorophenols), which also leave through the urine as less harmful chemicals, can stay in the body for several days. /chlorophenols/

2,4,6-Trichlorophenol was found in the urine of humans exposed to hexachlorocyclohexane.

2,4,6-Trichlorophenol was detected in chicken after exposure to 1,2,3,4,5,6-hexachlorocyclohexane.

... Corn and pea plants could metabolize pentachlorocyclohexene to the 2,4,6-trichlorophenol isomer.

For more Metabolism/Metabolites (Complete) data for 2,4,6-TRICHLOROPHENOL (9 total), please visit the HSDB record page.

Human studies indicate that sulfation and glucuronidation are the main metabolic pathways of 2,4,6-TCP, which is excreted in the urine as conjugated metabolites. In general, 2,4,6-TCP undergoes biotic isomerization to other trichlorophenol isomers and conjugation with glucuronic acid. Glucuronic acid accounts for approximately 80% of the conjugates detected in urine. Metabolites generated following incubation of 2,4,6-TCP are 2,6-dichloro-1,4-hydroquinone and two isomers of hydroxypentachlorodiphenyl ether. The 2,6-dichloro-1,4-semiquinone free radical was also identified. (L159)

The rate of excretion by rats of 2,4,6-trichlorophenol in urine and feces was studied. 6 Male wistar rats were dosed daily via stomach tube with a dose corresponding to 1 ppm of 2,4,6-trichlorophenol in the diet for 15 days. Storage of radioactivity reached a plateau after 3 days. At this level, excretion in the feces was 92.5% of the daily applied dose. Excretion decr after treatment stopped, reaching 4.3% in the urine and 1.9% in the feces after 3 days. 2,4,6-Trichlorophenol was conjugated and to a certain extent isomerized.

2,4,6-Trichlorophenol was investigated for its binding capacities to whole human serum and several human serum proteins in vitro. Percent binding to albumin and serum paralleled molecular wt, but no definite pattern was observed in ranking the percent binding to other proteins.

The concentration of 2,4,6-trichlorophenol was measured in the blood and various other tissues of the rat after ip administration of the compound at 25 mg/kg body weight. The highest concentration, 329 + or - 117 nmol per gram of tissue/, was found in the kidney. Half-times were between 1.4 and 1.8 hr in the blood, brain, fat, kidney, liver and muscle.

Urine from 230 Finnish sawmill workers exposed to a combination of 2,3,4,6-tetrachlorophenol (80%), 2,4,6-trichlorophenol (10-20%), and pentachlorophenol (5%), was analyzed for the sum of the three chemicals as chlorophenols. Samples were collected at the end of the work shift. Workers were divided into the following exposure groups according to work tasks: (I) primarily skin exposure (n= 112), (II) primarily respiratory tract exposure (n= 34), and (III) equal exposure by both routes (n= 84). Air concentrations at the workplace and amount of time spent with skin contact were not studied. There was no control group; values were compared to the nonexposed Finnish population level of <0.1 umol/L. Skin absorption was the most effective route of exposure as reflected by urinary chlorophenol concentrations. The median concentration in workers with skin absorption was 7.8 umol/L (range 0.1 to 210.9 umol/L) and was significantly different from that in workers with the respiratory tract as the main route of exposure (median concentration 0.9 umol/L; range 0.1 to 13.3 umol/L; p< 0.001) and from those with both routes of equal importance (1.4 umol/L; range 0.1 to 47.8 umol/L; p< 0.001).

/2,4,6-Trichlorophenol/ ... cleared rapidly from rats, most of it being excreted in the urine. 1 ug/g concentration of labeled phenol to the diet of rats /was added/ for a 3-day period. Eighty two percent of the dose was excreted in the urine and 22% in the feces. Radioactive trichlorophenol was not detected in liver, lung, or fat samples examined 5 days after the last dose was administered. ... 2,4,6-trichlorophenol is metabolized to 3,5-dichlorocatechol in the rabbit. Studies ... in the rabbit have shown that 2,4,6-trichlorophenol does not form a sulfate conjugate in vivo because of its low pK value.

2,4,6-Trichlorophenol is no longer used in the United States. It was previously used as an antiseptic; a pesticide for wood, leather, and glue preservation; and as an anti-mildew treatment. It was also used in the manufacture of other chemicals.

Used as an herbicide, defoliant, fungicide, and antimicrobial agent; as a wood preservative, glue preservative, insecticide ingredient, and anti-mildew treatment for textiles; in the synthesis of fungicides; Not commercially produced in the US; [HSDB] Used to make higher chlorinated phenols; [Merck Index]

Textiles (Fiber & Fabric Manufacturing) [Category: Industry]

For 2,4,6-trichlorophenol (USEPA/OPP Pesticide Code: 064212) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Fungicide, bactericide, wood preservative, biocide; intermediate in production of higher chlorinated phenols.

Herbicide, defoliant, fungicide /SRP: Former uses/

The 2,4,6-trichlorophenol produced as an intermediate product in the technical production of chloranil contained uP to 10.5 mg/kg of a mixture of 1,3,6,8- and 1,3,7,9-tetrachlorodibenzo-p-dioxin, but was free of any 2,3,7,8-tetrachlorodibenzo-p-dioxin.

1,3,6,8-Tetrachlorodibenzo-para-dioxin and 2,3,7-trichlorodibenzo-para-dioxin were found in a sample of 2,4,6-trichlorophenol at levels of 49 and 93 mg/kg, respectively. ... And tetra-, penta- and hexachlorodibenzofurans were found in one sample of 2,4,6-trichlorophenol.

In a Swedish sample of 2,4,6-trichlorophenol, 1.5 mg/kg 2,3,7,8-tetrachlorodibenzofuran was found, as well as 17.5, 36 and 4.8 mg/kg penta-, hexa- and heptachlordibenzofurans; less than 3 mg/kg polychlorinated dibenzo-para-dioxins were found.

(1976) 1000 kg (Principal US Customs Districts)

(1978) 2.72X10+5 G

(1980) 2.50X10+5 G

In the chlorination of 2,4-dichlorophenol it has been found that traces of amine, onium salts, or triphenylphosphine oxide are excellent catalysts to further chlorination by chlorine in the ortho position with respect to the hydroxyl function. During chlorination (80 °C, without solvent) these catalysts cause traces of 2,4,5-trichlorophenol (~500 - 1000 ppm) to be transformed into tetrachlorophenol. Thus these techniques leave no 2,4,5-trichlorophenol in the final product, yielding a 2,4,6-trichlorophenol of outstanding quality.

Chlorination of 2,6-dichlorophenol by chlorine at 70.C gives a yield of only 85%. Fifteen percent of the mixture is made up of 2,4,5,6,6-pentachloro-2-cyclohexen-1-one ... To avoid the formation of this kind of by-product, a direct attack by chlorine in the para position must be encouraged. This can be achieved by using catalysis based on a strong acid, or on a sulfur, an amine, or an onium salt. The yields can go as high as 98%.

Prepared by direct chlorination of phenol.

... Trichlorophenols are made industrially by chlorination of phenol with chlorine gas in a melt in cast-iron reactors. The isomer distribution in the product may be adjusted to market demands by the chlorination level and by recycling various intermediates. The yield, based on chlorine and phenol, is greater than 95 %. /Trichlorophenols/

Addition of chlorine to phenol at 65 to 130 °C and 1.3 atmospheres with an aluminum chloride catalyst. The products (2,4,6-trichlorophenol, 2,3,4,6-tetrachlorophenol and pentachlorophenol) are separated by batch vacuum distillation.

2,4,6-Trichlorophenol is available in the USA in aqueous formulations.

2,4,6-Trichlorophenol available in Japan has a purity of 97%.

Phenol, 2,4,6-trichloro-: ACTIVE

2,4,6-Trichlorophenol was /first/ prepared in 1836. Commercial production of 2,4,6-trichlorophenol in the USA was first reported in 1950.

... Highly toxic polychlorinated dibenzo-p-dioxins may be formed during the chemical synthesis of some chlorophenols, and the amount of contaminant formed is dependent upon the temperature and pressure control of the reaction. /Chlorinated phenols/

Production of this chemical was discontinued in 1975 by the Dow Chemical Company, the only manufacturer of 2,4,6-trichlorophenol in the United States, because of the high cost of removing highly toxic dioxin impurities.

2,4,6-Trichlorophenol is not produced in the US.