1,2,3-트라이클로로벤젠

log Kow = 4.05

4.05

1.69 at 77 °F (USCG, 1999) - Denser than water; will sink

1.4533 g/cu cm at 25 °C

1.45 g/cm³

1.4533 @25 °C

Platelets from alcohol

White crystals

Insoluble (NTP, 1992)

Slightly soluble in ethanol; very soluble in ether and benzene

Sparingly sol in alcohol; freely sol in carbon disulfide

In water, 18 mg/L at 25 °C.

Solubility in water: very poor

234.9 °F (NTP, 1992)

113 °C

112.7 °C (closed cup)

112.7 °C c.c.

424 to 426 °F at 760 mmHg (NTP, 1992)

218.5 °C

218.5 °C

218.5 °C @760 [mm Hg]

126.7 °F (NTP, 1992)

51.3 °C

53.5 °C

51.3 °C

This chemical does not meet GHS hazard criteria for 0.7% (1 of 153) of reports.

Warning

H302 (30.7%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P272, P273, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 153 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

This chemical does not meet GHS hazard criteria for 11.9% (5 of 42) of reports.

Chemical: Benzene, 1,2,3-trichloro-

Hazard Traits - Bioaccumulation; Environmental Persistence

Status: Active Update: 03-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/1948

1,2,3-Trichlorobenzene: Does not have an individual approval but may be used under an appropriate group standard

Special Hazards of Combustion Products: May emit toxic hydrogen chloride and phosgene gases in fire.

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

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1,2,3-Trichlorobenzene is included on this list. Effective date 10/4/82; Sunset date: 10/4/92.

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. Trichlorobenzenes are produced, as an intermediate or final product, by process units covered under this subpart. /The standards apply to all of the isomers and mixtures./

Fire Extinguishing Agents: Small fires: dry chemical, carbon dioxide, water spray or foam; large fires: water spray, fog or foam. (USCG, 1999)

Use water spray, dry powder, foam, carbon dioxide.

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. 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. Give one or two glasses of water to drink. 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.

Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may spread fire. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide.

Water, foam, carbon dioxide, dry chemical

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a POTW is acceptable only after review by the governing authority. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must meet Hazardous Material Criteria for disposal.

Land spill. Dig a pit, pond, lagoon, holding area to contain liquid or solid material. 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. Water spill. Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. If dissolved, in region of 10ppm or greater concentration, 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. Air spill. Apply water spray or mist to knock down vapors. Combustion products include corrosive or toxic vapors. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./

SMALL SPILLS AND LEAKAGE: You should dampen the solid spill material with acetone, then 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 adsorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a strong soap and water solution. Do not reenter the contaminate area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

SRP: Criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

The following wastewater treatment technology has been investigated for 1,2,3-trichlorobenzene: biological treatment.

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. Carefully collect remainder. Then store and dispose of according to local regulations.

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.

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. Personnel protection. Avoid breathing vapors Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. ...

1,2,3-Trichlorobenzene has been detected in human blood samples (whole blood) in Canada at a concn of 1.17 ng/g(1) and in 66 of 108 samples of human adipose tissue at a mean concn of 44 ng/g(2). A survey of human milk from the general population of Canada found 1,2,3-trichlorobenzene in 17% of the samples at an avg concn of 2 ppb(3). 1,2,3-Trichlorobenzene was detected in human milk in Yugoslavia at <5 ug/kg(4) and human milk in Canada at 0.07 ng/g (whole milk) and 2.79 ng/g (milk fat)(5). A 1992 epidemiologic study of 497 Canadian samples resulted in 54.1% positive detection of 1,2,3-trichlorobenzene at a median concn of 1.9 ng/g lipid with a 236 ng/g lipid maximum concn(6).

EC50; Species: Chlorella vulgaris (Green algae, age 3-4 days, exponential growth phase, 20X10+4 cells/mL); Conditions: static, 19 °C, pH 6.5; Concentration: 34 mmol/cu m for 3 hr; Effect: physiology, photosynthesis /formulated product/

EC50; Species: Pseudokirchneriella subcapitata (Green algae, initial concentration 500000 cells/L); Conditions: static, 20 °C; Concentration: 900 ug/L for 96 hr; Effect: general growth

EC50; Species: Daphnia magna (Water flea); Conditions: freshwater, renewal, 25 °C, pH >7; Concentration: 2000 ug/L for 24 hr; Effect: behavior, equilibrium /formulated product/

EC50; Species: Daphnia magna (Water flea); Conditions: freshwater, static; Concentration: 350 ug/L for 24 hr; Effect: intoxication, immobilization

For more Ecotoxicity Values (Complete) data for 1,2,3-TRICHLOROBENZENE (21 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 1380(2) to 7943(3), indicate that 1,2,3-trichlorobenzene is expected to have low to no mobility in soil(SRC). Volatilization of 1,2,3-trichlorobenzene from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 1.25X10-3 atm-cu m/mole(4). However, adsorption to soil is expected to attenuate volatilization(SRC). 1,2,3-Trichlorobenzene is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.21 mm Hg(4). 1,2,3-Trichlorobenzene is expected to biodegrade slowly in soils with biodegradation half-lives ranging from several weeks to several months(5-7).

AQUATIC FATE: Based on a classification scheme(1), Koc values of 1380(2) to 7943(3), indicate that 1,2,3-trichlorobenzene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon a Henry's Law constant of 1.25X10-3 atm-cu m/mole(5). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 4.9 hours and 5.6 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column(SRC). According to a classification scheme(6), BCF values of 130 in carp(7) to 245,470 in fathead minnow(2), suggest bioconcentration in aquatic organisms is high to very high(SRC). 1,2,3-Trichlorobenzene is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(4). Biodegradation of 1,2,3-trichlorobenzene is expected to occur slowly, with half-lives ranging from several weeks to several months(8-10).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,2,3-trichlorobenzene, which has a vapor pressure of 0.21 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,2,3-trichlorobenzene 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 57 days(SRC), calculated from its rate constant of 2.8X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). In the laboratory, 1,2,3-trichlorobenzene irradiated at wavelengths greater than 285 nm has been shown to undergo both direct and sensitized dechlorination and isomerization(4).

Seed oils and meat samples from Yugoslavia contained 1.5 and 1.0 ng/g fresh weight of 1,2,3-trichlorobenzene, respectively(1). 1,2,3-Trichlorobenzene was detected in leafy vegetables at a concn of 0.00011 ug/g(2). 1,2,3-Trichlorobenzene was detected in potato core (0.05 ug/kg), inner parts of onions (0.0498 ug/kg), outer parts of onions (0.0175 ug/kg), and tomato flesh (0.0467 ug/kg)(3).

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

Oral (T38) ; inhalation (T38) ; dermal (T38)

ENVIRONMENTAL: A survey of human milk from the general population of Canada found 1,2,3-trichlorobenzene in 17% of the samples at an avg concn of 2 ppb(1). 1,2,3-Trichlorobenzene was detected in human milk in Yugoslavia at <5 ug/kg(2) and human milk in Canada at 0.07 ng/g (whole milk) and 2.79 ng/g(milk fat)(3). A 1992 epidemiologic study of 497 Canadian samples resulted in 54.1% positive detection of 1,2,3-trichlorobenzene at a median concn of 1.9 ng/g lipid with a 236 ng/g lipid maximum concn(4).

/AQUATIC SPECIES/ The growth rate reduction of mosquito fish (Gambusia affinis) fry was investigated with a range of sublethal exposure levels of four halobenzenes for 42 days. These compounds were found to produce growth rate reduction in mosquito fish fry at concentrations as low as 0.30, 0.18, 0.025, and 0.010 umol/L for 1,4-dibromobenzene, 1,2,3-trichlorobenzene, 1,2,4-tribomobenzene, and pentachlorobenzene, respectively. The aqueous exposure concentrations causing growth rate reduction of 50 and 10% (EC50 and EC10, respectively) for the halobenzenes were 0.067-3.4 and 0.0042-0.32 umol/L, respectively. The EC50 and EC10 values are within the ranges of 5 to 8% and 0.1 to 3.9% of the LC50 values, respectively. The percentage of growth rate reduction relative to the LC50 could possibly be used to describe chronic toxicity effects of organic compounds with the aquatic organisms. The internal concentrations obtained from the analysis for the halobenzenes were generally consistent with the calculated internal concentrations. The lipid-based internal concentrations that gave 50 and 10% growth rate reductions were 8.3-27 and 0.5-1.6 umol/kg, respectively. These values have a more limited range than the corresponding external aqueous concentrations. The quantitative structure-activity relationships between the internal concentrations at 50 and 10% growth rate reduction and physicochemical parameters were found to be less satisfactory than those based on external aqueous concentrations.

/AQUATIC SPECIES/ The sensitivity of the early life stage (ELS) toxicity test for two compounds with different modes of action was determined, and related to other toxicity tests with the same compounds. The zebrafish. Danio rerio, was used as a test organism, and the two model compounds were 1,2,3-trichlorobenzene, a non-polar narcotic, and parathion, an acetylcholinesterase (AChE) inhibitor. Hatching and survival after 28 days were significantly reduced in the highest 123TCB treatment (263 ug/L), but not in any of the parathion treatments. Growth of the larvae was negatively affected at parathion concentrations above 20 ug/L, while AChE was only significantly inhibited at the highest concentration, 93 ug/L. No effects on growth were found in the 123TCB treatments. In comparison with acute and chronic studies with both compounds, the ELS test turned out to be less sensitive than chronic studies and more sensitive than acute studies. The difference in sensitivity between the tests systems seems however, to depend on the mode of action of the compound.

/AQUATIC SPECIES/ A chronic toxicity experiment was performed with zebrafish, Danio rerio, exposed to 1,2,3-trichlorobenzene (123TCB). Fish were exposed in a flow-through system for 68 and 147 days. Parameters measured are survival, growth, reproduction, and glycogen and protein content. The only parameter which was influenced was the number of eggs produced per female, resulting in an EC(50) of 40 ug/L. Using this value and acute toxicity data for 123TCB, an acute to chronic ratio (ACR) of 80 was calculated, which is larger than ACRs for other species exposed to nonpolar narcotics.

Mean concns of 0.01 ppm 1,2,3-trichlorobenzene were found in residues from ten herring gull eggs sampled along the Detroit River and ten from the Niagara River in 1979(1). Samples of Arctic fox (Alopex lagopus) muscle and liver taken from Barrow, AK, Holman, NT, and Arviat, NU had total chlorobenzene concns of 4.2-17.6 ng/g (wet weight), of which 1,2,3-trichlorobenzene is included(2).

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1,2,3-Trichlorobenzene is included on this list. Effective date 10/4/82; Sunset date: 10/4/92.

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. Trichlorobenzenes are produced, as an intermediate or final product, by process units covered under this subpart. /The standards apply to all of the isomers and mixtures./

... Five days after the oral administration of 1,2,3-trichlorobenzene to rabbits, 78% ... of the administered dose was excreted as monophenols.

Approximate half-life of 1,2,3-trichlorobenzene is 2 days.

1,2,3-trichlorobenzene is metabolized to n-acetyl-s-(2,3,4-trichlorophenyl)-l-cysteine, 2,3,4-trichlorophenol, & 3,4,5-trichlorophenol in rabbits. /from table/

In metabolic studies with rabbits using each of the 3 isomeric trichlorobenzenes at 0.5 g/kg, 1,2,3-trichlorobenzene was the one most rapidly metabolized ... in 5 days, 62% ... underwent glucuronic conjugation. The major metabolite was 2,3,4-trichlorophenol; small amt of 3,4,5-trichlorophenol, 3,4,5-trichlorocatechol, & mercapturic acid were ... detected.

Trichlorobenzene is absorbed via oral, inhalation, and dermal routes. It is believed to be metabolized via cytochrome p-450 enzymes into metabolites that include phenols, mercapturic acid, and catechols.(T38)

... Five days after the oral administration of 1,2,3-trichlorobenzene to rabbits, 78% ... of the administered dose was excreted as monophenols.

All three isomers of trichlorobenzene were absorbed from the gastrointestinal tract, intact skin, and lung.

The tissue distribution and elimination of 1,2,3-trichlorobenzene, 1,2,4-trichlorobenzene, and 1,3,5-trichlorobenzene were examined in male Sprague Dawley rats. Fasted animals were given single doses of 10 mg/kg of the (14)C labeled isomers by gavage. Serial sacrifices were performed at 0.5, 1, and 24 hr and 1, 2, 7, 14, 28, and 56 days post administration. Radioassays utilized the liver, kidneys, spleen, brain, pancreas, lung, heart, thigh muscle, skin, perirenal fat, testes, bladder, adrenals, epididymis, seminal vesicles, prostate, gastrointestinal tract, blood, and salivary glands. The data for each tissue was fitted to a linear compartmental pharmacokinetic model. The amount of (14)C excreted in urine and feces was determined daily for 1,2,3-trichlorobenzene and 1,3,5-trichlorobenzene isomers. Radioactivity from the labeled isomers appeared in the blood and tissues within 30 min of administration, peaked at approximately 4 hr, and slowly declined to background levels. Radioactivity attributed to 1,2,4-trichlorobenzene dropped to background levels after 28 days. The bladder, kidney, fat, skin, liver, and adrenals showed high 1,2,4-trichlorobenzene activity up to 24 hr post treatment. Radioactivity due to 1,2,3-trichlorobenzene dropped to background levels after 56 days for liver, fat, and skin and 28 days for the other tissues. The highest 1,2,3-trichlorobenzene concentrations were found in liver, fat, kidney, and bladder. Significant levels of radioactivity from 1,3,5-trichlorobenzene remained in the tissues after 56 days for all tissues examined. Approx 85% of 1,3,5-trichlorobenzene and 92% of the 1,2,3-trichlorobenzene were excreted within 24 hr of dosing. Compartmental analysis showed 1,3,5-trichlorobenzene to have the highest values for the linear coefficients of exponential decay.

Used as an intermediate, dye carrier, transformer fluid, solvent, coolant, and heat transfer medium; Used in lubricants and insecticides; [HSDB]

Chem intermediate eg, for 2,3-dichlorophenol; constituent of trichlorobenzene mixt used for termite control /SRP: Former use/ and as transformer fluid; dye carrier & solvent

Solvent for high melting products; Coolant in electrical installations and glass tempering; Polyester dyeing; Lubricants; Heat transfer medium, insecticides.

Organic intermediate

Trichlorobenzene ... has been used as a soil treatment to repel or poison termites around the foundation of buildings. The technical product is a mixture of the 1,2,3- and 1,2,4- isomers. /Former use/

Trichlorobenzene is used as a solvent in chemical manufacturing, as well as in dyes, dielectric fluid, synthetic transformer oils, lubricants, heat-transfer medium, and insecticides. (T39)

(1979) 1.4X10+9 G-PRINCIPAL CUSTOMS DISTRIBUTORS

(1983) 1.39X10+9 g /1,2,3- AND 1,2,4-TRICHLOROBENZENE/

(1982) 51,300 to 163,000 lb

Benzene, 1,2,3-trichloro- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#3183]

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#3184]

... Production method applicable to 1,2,4- and 1,2,3-trichlorobenzenes is based on the dehydrohalogenation of 1,2,3,4,5,6-hexachlorocyclohexane (stereoisomeric mixture), a byproduct of gamma-hexachlorocyclohexane production. In the presence of aqueous alkali or alkaline earth solutions or of ammonia, or directly through use of catalysts, hexachlorocyclohexane is converted at a temperature of 90 - 250 °C mainly to trichlorobenzene. The yield lies between 80 and 99%, with the product mixture consisting of 70 - 85% 1,2,4-trichlorobenzene and 13 - 30% 1,2,3-trichlorobenzene.

The batch reaction of benzene with a 2.8-fold molar quantity of chlorine in the presence of ferric chloride at temperatures increasing to 100 °C gives a chlorination mixture consisting of 26% 1,4-dichlorobenzene, 4.5% 1,2-dichlorobenzene, 48% 1,2,4-trichlorobenzene, 8% 1,2,3-trichlorobenzene, 8% 1,2,3,4-tetrachlorobenzene, 5.5% 1,2,4,5-tetrachlorobenzene, and less than 1% pentachlorobenzene. The proportion of 1,4-dichlorobenzene, and thus also of 1,2,4-trichlorobenzene, can be raised by adding sulfur compounds as cocatalysts. After the chlorination mixture has been neutralized it can be separated by fractional distillation provided a column with more than 60 practical plates is used.

Chlorination of o-dichlorobenzene in the presence of ferric chloride, followed by distillation.

Benzene, 1,2,3-trichloro-: ACTIVE

1,2,3-Trichlorobenzene is formed in minor amounts during the production of monochlorobenzene.