1,3,5-Trichlorobenzene

log Kow = 4.19

4.15

1.456 g/cu cm at 20 °C (liquid)

Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.0

Needles

White crystals

Long needles

less than 0.1 mg/mL at 67.1 °F (NTP, 1992)

Soluble in chloroform

Sparingly sol in alcohol; freely sol in ether, benzene, petroleum ether, carbon disulfide, glacial acetic acid

In water, 6.01 mg/L at 25 °C

Solubility in water, g/100ml at 25 °C: 0.0006

224.6 °F (NTP, 1992)

107 °C

107 °C /closed cup/

107 °C

407.1 °F at 760 mmHg (NTP, 1992)

208 °C

1,3,5-Trichlorobenzene forms azeotropes with percentages of the following compounds yielding boiling points as listed: 50% camphor, bp 210.5 °C; 43% caproic acid, bp 204.0 °C; 60% m-Cresol, bp 200.5 °C; 40% p-Cresol, bp 200.2 °C; 35% N-Ethylaniline, bp 203.0 °C; Methone (% NA), bp 209.5 °C; 95% Phenol, bp 181.3 °C; p-Toluidine (% NA), bp 199.0. /From table/

208 °C

145 to 147 °F (NTP, 1992)

62.8 °C

63 °C

This chemical does not meet GHS hazard criteria for 7.8% (4 of 51) of reports.

Warning

H302 (88.2%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 51 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H401: Toxic to aquatic life [Hazardous to the aquatic environment, acute hazard]

Chemical: Benzene, 1,3,5-trichloro-

Hazard Traits - Bioaccumulation; Environmental Persistence

Benzene, 1,3,5-trichloro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, 1,3,5-trichloro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.

Status: Active Update: 22-09-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/34071

Benzene, 1,3,5-trichloro-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

This chemical is combustible. (NTP, 1992)

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

USEPA; Ambient Water Quality Criteria Doc: Chlorinated Benzenes (1980) EPA 440/5-80-028.

USEPA; Health Assessment Document: Chlorinated Benzenes (1985) EPA-600/8-84-015.

Bobra A et al; Quantitative Structure-Activity Relationships for the Acute Toxicity of Chlorobenzenes to Daphnia magna; Environ Toxicol Chem 4 (3): 297- 305 (1985). The relationships between physical-chemical properties of aqueous solubility, octanol/water partition coefficient, vapor pressure, boiling and melting point, and Henry's Law constants are discussed and illustrated for the chlorobenzenes.

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. 1,3,5-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./

/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. /Trichlorobenzenes, liquid/

/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. ... 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. /Trichlorobenzenes, liquid/

/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 m (150 ft) for liquids and at least 25 m (75 ft) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas. /Trichlorobenzenes, liquid/

/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. /Trichlorobenzenes, liquid/

For more DOT Emergency Guidelines (Complete) data for 1,3,5-TRICHLOROBENZENE (8 total), please visit the HSDB record page.

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

Use water spray, powder, foam, carbon dioxide.

Fresh air, rest. Refer for medical attention.

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

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

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.

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 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.

SRP: At the time of review, 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 1,3,5-trichlorobenzene: biological treatment.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. 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 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. ... 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.

1,3,5-Trichlorobenzene has been detected in human blood samples (whole blood) in Canada at a concentration of 4.02 ng/g(1) and in 19% of human adipose tissue at a mean concentration of 126 ng/g(2). Combined trichlorobenzene and tetrachlorobenzene isomers were detected in human adipose tissue in Slovenia at a concentration of 60 ng/g and in human hair samples at 40 ng/g(3). 1,3,5-Trichlorobenzene was detected in human milk in Yugoslavia at concentrations of 0-3 ppb(4) and human milk in Canada at avg concentrations of 0.04 ng/g (whole milk) and 1.4 ng/g (milk fat)(5).

LD50; Species: Oncorhynchus mykiss (Rainbow trout weight 9.1-43.2 g, length 7.6-9.6 cm); Conditions: freshwater, gavage, 13.3-14.1 °C, pH 8.04-8.21, alkalinity 86 mg/L CaCO3, dissolved oxygen 8.0-10.0 mg/L; Concentration: 39.6 mmol/kg /formulated product/

LD50; Species: Oncorhynchus mykiss (Rainbow trout weight 9.0-30.4 g, length 7.0-9.9 cm); Conditions: freshwater, ip, 13.9-16.2 °C, pH 8.00-8.25, alkalinity 86 mg/L CaCO3, dissolved oxygen 9.1-9.8 mg/L; Concentration: 30.5 mmol/kg /formulated product/

LC50; Species: Poecilia reticulata (guppy); Concentration: 3.3 ppm for 14 days /Conditions of bioassay not specified/

EC50; Species: Tetrahymena pyriformis (Ciliate); Conditions: static, 30 °C; Concentration: 30000 ug/L for 24 hr /formulated product/

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 2.8(2) to 3.82(3), indicate that 1,3,5-trichlorobenzene is expected to have low to no mobility in soil(SRC). Volatilization of 1,3,5-trichlorobenzene from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 1.89X10-3 atm-cu m/mole(4). However, adsorption to soil is expected to attenuate volatilization(SRC). 1,3,5-Trichlorobenzene is expected to biodegrade slowly in soil with biodegradation half-lives ranging from several weeks to months(5-7).

AQUATIC FATE: Based on a classification scheme(1), log Koc values of 2.8(2) to 3.82(3), indicate that 1,3,5-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 1.89X10-3 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 4.6 hours and 5.5 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 50 days if adsorption is considered(6). According to a classification scheme(7), BCFs of 150(8) to 14,000(9), suggest bioconcentration in aquatic organisms is high to very high(SRC). 1,3,5-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 1,3,5-trichlorobenzene is expected to occur slowly, with half-lives ranging from several weeks to months(10-12).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,3,5-trichlorobenzene, which has a vapor pressure of 0.24 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,3,5-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 24 days(SRC), calculated from its rate constant of 6.8X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 1,3,5-Trichlorobenzene has been shown to be susceptible to direct photolysis by sunlight(4).

1,3,5-Trichlorobenzene was detected in corn oil at 0.7 ppm and sunflower oil at 0.02 ppm(1). 1,3,5-Trichlorobenzene was detected in leafy vegetables at a concentration of 0.28 ng/g, in fruit at 0.12 ng/g and in eggs/meat at 0.7 ng/g(2). 1,3,5-Trichlorobenzene was detected (concentration in ug/kg) in potato cores (0.0090), potato peels (0.0140), inner part of onions (0.0304), outer onion (0.0488), pea seeds (0.0391) and pea pods (0.159)(3).

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

Inhalation (T38) ; oral (T38) ; dermal (T38)

1,3,5-Trichlorobenzene was detected in human milk in Yugoslavia at concentrations of 0-3 ppb(1) and human milk in Canada at average concentrations of 0.04 ng/g (whole milk) and 1.4 ng/g (milk fat)(2). 1,3,5-Trichlorobenzene was detected in milk at concentrations of 1.2 ng/g(3).

/AQUATIC SPECIES/ A test was developed using Tetrahymena pyriformis in order to determine the toxicity of various chemicals. Precultured Tetrahymena pyriformis was exposed for 24 hr at 30 °C to various concn of chemicals, and the number of Tetrahymena pyriformis surviving was then counted. The concn of the chemical, at which the proliferation of Tetrahymena pyriformis was restricted to one-half of the blank test (EC50), was determined. The method, applied to 57 chemicals /including 1,3,5-trichlorobenzene/, demonstrated that it could be used to detect the chemicals at low concn rapidly and with ease. The EC50 values showed a good relationship with 48 hr LC50 values for Himedaka (Oryzias latipes), and could be explained on the basis of the partition coefficient between water and n-octanol.

Cough. Sore throat.

Redness. Pain.

Trichlorobenzene irritates the eyes and respiratory tract. (T20)

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. 1,3,5-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./

1,3,5-Trichlorobenzene is metabolized to chlorobenzene and 2,4,6-tichlorophenol in rabbits ... . /From table/

In metabolic studies with rabbits using each of the 3 isomeric trichlorobenzenes at 0.5 g/kg ... 1,3,5-trichlorobenzene was least rapidly metabolized. ... Practically no ethereal sulfate or mercapturic acid /was formed/, & only phenol formed was 2,4,6-trichlorophenol.

... Five days after the oral administration of 1,3,5-trichlorobenzene to rabbits, 9% ... of the administered /cmpd/ was excreted as monophenols.

Im injection of approx 50 mg/kg trichlorobenzene to hens resulted in polychlorobenzenes in the yolk in amounts of 2.5 to 6.1% of the admin dose. The egg white contained almost no residue. 1,3,5-Trichlorobenzene was metabolized to 2,4,6-trichlorophenol.

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

... 1,3,5-Trichlorobenzene was admin orally to rats at 2 mg/kg, and ... /appeared/ in fat at greater concentration than in liver, kidneys, heart, or blood.

... Five days after the oral administration of 1,3,5-trichlorobenzene to rabbits, 9% ... of the administered /cmpd/ was excreted as monophenols.

All three isomers of trichlorobenzene are 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. Approximately 85% of the 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 a solvent (degreasing and dyes), dielectric fluid, lubricant additive, emulsifier, and chemical intermediate; [HSDB]

Metal Degreasing [Category: Clean]

Component in trichlorobenzene mixture as dye solvent, degreasing solvent, dielectric fluid, and as lubricant additive

/Manufactured/ and /used/ as an industrial chemical, chemical intermediate, solvent and emulsifier.

1,3,5-Trichlorobenzene is used ... as a termite preparation and insecticide ... /and is/ found as /an/ unintended by-product of the manufacture of mono- and dichlorobenzenes. /SRP: 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)

(1972) 1.3X10+6 G (Principal customs distributors)

(1975) 1.5X10+7 G (Principal customs distributors)

2023: 16,335 lb

(1972) Not produced commercially in US

(1975) Not produced commercially in US

... By Sandmeyer reaction on 3,5-dichloroaniline, by reaction of benzene-1,3,5-trisulfonic acid derivatives with phosgene, by vapor phase chlorination of 1,3-dichlorobenzene, and by chlorination of 3,5-dichloronitrobenzene or 1-bromo-3,5-dichlorobenzene at 300 - 400 °C. The proportion of the 1,3,5-isomer in a mixture can be raised by isomerization of the other trichlorobenzenes with aluminum chloride or by reacting tetrachlorobenzenes and higher chlorobenzenes with alkali metal amides. Total isomerization is reported to occur when SbF5 - HF is used as a catalyst system. The three trichlorobenzenes can be separated by distillation and crystallization.

Prepared from 2,4,6-trichloroaniline by diazotization and treatment with alcohol ... .

Diazotization of 2,4,6-trichloroaniline, followed by treatment with a reducing agent such as hypophosphorous acid.

All Other Basic Organic Chemical Manufacturing

Benzene, 1,3,5-trichloro-: ACTIVE