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Home > Encyclopedia > 1,3,5-Trichlorobenzene

1,3,5-Trichlorobenzene

1,3,5-Trichlorobenzene structure

1,3,5-Trichlorobenzene 

structure
  • CAS No:

    108-70-3

  • Formula:

    C6H3Cl3

  • Chemical Name:

    1,3,5-Trichlorobenzene

  • Synonyms:

    Benzene,1,3,5-trichloro-;1,3,5-Trichlorobenzene;sym-Trichlorobenzene;s-Trichlorobenzene;Symmetrical trichlorobenzene;NSC 4389

  • Categories:

    Organic Chemistry  >  Hydrocarbons and Derivatives

Description

white to beige crystalline powderWhite to off-white crystals.


1,3,5-trichlorobenzene appears as white to off-white crystals. (NTP, 1992)|WHITE-TO-YELLOW CRYSTALS OR POWDER WITH CHARACTERISTIC ODOUR.


1,3,5-trichlorobenzene appears as white to off-white crystals. (NTP, 1992)|1,3,5-trichlorobenzene is a trichlorobenzene carrying chloro substituents at positions 1, 3 and 5.

1,3,5-Trichlorobenzene Basic Attributes

181.44700

181.45

203-608-6

2HS4M0BX3C

0344

4389

DTXSID8026195

Needles|White crystals|Long needles

2903999090

Characteristics

0

3.64680

1,3,5-trichlorobenzene appears as white to off-white crystals. (NTP, 1992)

1 x 10-6 g/cm3 @ Temp: 100 °C

63.5 °C

208 °C @ Press: 763 Torr

126ºC

1.5662 (20ºC)

soluble in benzene, ether, ligroin (Weast, 1986), glacial acetic acid, carbon disulfide, and petroleum ether (Windholz et al., 1983);Solubility in water, g/100ml at 25°C: 0.0006

0-6ºC

0.267mmHg at 25°C

6.26 (NTP, 1992) (Relative to Air)

Drinking water standard: No MCLGs or MCLs have been proposed, however, a DWEL of 200 μg/L was recommended (U.S. EPA, 2000).

0.00 atm-m3/mole|Henry's Law constant = 1.89X10-3 atm-cu m/mol at 25 °C

Volatile with steam|Enthalpy of fusion: 18.1 kJ/mol|Hydroxyl radical reaction rate constant = 6.8X10-13 cu cm/molec-sec at 25 °C (est)

Insoluble in water.

Aryl Halides

Can react vigorously with oxidizing materials. (NTP, 1992).

278.8 J/g at 100 °C; 259.2 at 150 °C; 239.1 at 200 °C

Critical temperature: 470.8 °C; Critical pressure: 3.01 mPa

Safety Information

III

9

UN 3077

3

R22; R38

S36/37

DC2100100

Xn

Separated from strong oxidants. Keep in a well-ventilated room.

Stable. Incompatible with acids, strong oxidizing agents.

P261-P273-P280-P305 + P351 + P338

H302 + H312 + H332-H315-H319-H335-H412

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.

... Can react vigorously with oxidizing materials.|... On contact with acids or acid fumes they evolve highly toxic /hydrogen chloride fumes/ /Chlorides/

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.

This chemical is combustible. (NTP, 1992)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 49 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P271, P301+P312, P304+P340, P305+P351+P338, P312, P314, P330, P337+P313, P403+P233, P405, and P501

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. STORAGE PRECAUTIONS: You should store this material in a refrigerator. STORE AWAY FROM SOURCES OF IGNITION. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)|Wear appropriate chemical protective gloves, boots and goggles. Wear positive pressure self-contained breathing apparatus when fighting fires involving this material.

Moderate when exposed to heat or flame.

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: 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.

/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.

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.

Chlorinated benzenes are irritating to the skin, conjunctiva, and mucous membranes of the upper respiratory tract. ... /Chlorinated benzenes/

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.

Separated from strong oxidants. Keep in a well-ventilated room.

A harmful contamination of the air will be reached rather slowly on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.

The substance is irritating to the eyes and respiratory tract.

NO open flames.

Use local exhaust or breathing protection.

Protective gloves.

Wear safety goggles or eye protection in combination with breathing protection.

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 was detected at a concn of 26 mg/L in industrial discharge in the Holston River, TN. 1,3,5-Trichlorobenzene was detected at a concn of 0.2 ug/L in municipal waste water at the Orange County Sewage Dept, CA. 1,3,5-Trichlorobenzene was detected in 7 mile effluent and municipal waste water at the sewage treatment works, Hyperion, LA at a concn of 0.9 ug/L (Fall, 1976) and <0.2 ug/L (Summer, 1976). 1,3,5-Trichlorobenzene was detected in municipal waste water at Oxnard, Ca, sewage treatment plant at concn of 0.4 ug/L (fall, 1976) and <0.01 ug/L (summer, 1976).|In 1978, 1,3,5-trichlorobenzene was detected in major Southern California Municipal wastewaters in samples taken at 8 stations; concns were 0.007-2.2 and <0.01-0.03 ppb in summer and winter, respectively(1). Los Angeles County effluent had avg concns of 0.035 ppb of 1,3,5-trichlorobenzene from samples taken Nov 1980 to Aug 1981(2). Combined trichlorobenzene isomers were detected at concns of 50-1,900,000 ng/cu m in the effluent of a waste gasification and combustion pilot plant(3). 1,3,5-Trichlorobenzene was detected at concns of 0.64 and 0.28 ng/cu m in the effluent of a hazardous waste incinerator in Biebesheim, Germany(4). 1,3,5-Trichlorobenzene was detected in the effluent of paper mills in Finland at concns of 0.1-5.9 ug/L(5). 1,3,5-Trichlorobenzene was detected at an avg conc of 1.22 mg/kg in sewage sludge from the UK(6). 1,3,5-Trichlorobenzene had an avg concn of 0.0022 ug/L and a frequency of 3.3% in sources feeding low land rivers in England and Wales in 1995 and an avg concn of 6.86 ug/L with a frequency of 21% in trade effluents(7). Effluent from a municipal waste pilot combustion facility had an avg emission of 93.69 ng/cu m(8).

SEDIMENT: 1,3,5-Trichlorobenzene was detected in Niagara River suspended sediments at the following levels: Niagara-on-the-Lake, 1980, 28 samples, 93% pos, avg 20 ppb dry wt(1); 1981, 5 stations, range of avgs, 3-53 ppb(2); 1981, settling particles, 5.3 ppb(3). Surficial sediments, Lake Superior, 13 sites, 46% pos, not detected-0.4 ppb, avg of pos 0.2 ppb, Lake Huron, 42 sites, 90% pos, not detected-4 ppb, avg pos 0.7 ppb, Lake Erie, 5 sites, 100% pos, 0.1-5 ppb, avg pos 1 ppb, Lake Ontario, 11 sites, 100% pos, 7-250 ppb, avg pos 60 ppb(4). Lake Ontario, Niagara River vicinity, 1982: 20 m sediment traps, 6 stations, 83% pos, 2.4-5.2 ppb; 3 sites, avg, ppb (depth, m): 5.5 (20), 7.0 (40), 8.6( 60), 9.5 (68)(5). Concn (ppm dry wt) in sediments: Southern Lake Huron, 9 samples, 0.1-0.5, 0.3 avg; Lake St. Clair, 2 samples, 3.6-10, 6.8 avg: Western Lake Erie, 9 samples, 0.8-12, 3.1 avg; Central Lake Erie, 22 samples, not detected-1.0, 0.6 avg; Eastern Lake Erie, 15 samples, not detected-1.7, 0.9 avg(6). Mean 1,3,5-trichlorobenzene concns of 0.2, 0.7, 1 and 60 ppb were detected in the superficial sediments from Lakes Superior, Huron, Erie, and Ontario, respectively(7).|SEDIMENT: Lake Ketelmeer, in The Netherlands, has been analyzed for pollutants since 1940; 1,3,5-Trichlorobenzene was detected in the sediment at concns of 130 ng/kg (1965)(1), 50 ng/kg (1985)(1), and 20-120 ug/kg (1995)(2). 1,3,5-Trichlorobenzene was also detected at concns of 59 ug/kg (dry weight) in the top layer and at 137 and 144 ug/kg (dry weight) in core samples from Lake Ketelmeer collected in 1999(3). 1,3,5-Trichlorobenzene was detected at concns of 0.1-39.2 ng/g in sediment from Ise Bay, Japan(4). 1,3,5-Trichlorobenzene was detected at maximum concns of 4, 5 and 12 ng/g in sediment taken from the Scheldt Estuary, Netherlands(5). 1,3,5-Trichlorobenzene was detected in sediment off the coast of Taiwan at concns of 1-24 ng/kg from samples taken April to Oct 1995(6) and in Lake Ladoga, Russia at concns of 0-3.9 ng/g(7). 1,3,5-Trichlorobenzene was found off the coast of Kaohsiung, Taiwan at 40 sites at concns of not detected to 78.3 ng/g in samples taken 1996(8). 1,3,5-Trichlorobenzene was not detected in suspended solids in the Rhone River at Bouveret, Pougny, and Pioncare, but was detected at Saone, Chasse, St. Vallier, Beauchastel, Donzere, and Arles at 9.7, 475, 5.3, 28.7, 8.8, and 220 ug/kg (dry weight), respectively(9). Bed sediment samples taken from the Rhone River had concns of 1,3,5-trichlorobenzene of not detected, 9.3, 11.4, and 16.2 ug/kg (dry weight) from samples taken near Seyssel, Cordrieu, Beauchastel, and Arles, respectively(9). 1,3,5-Trichlorobenzene was detected in sediment in 7 of 7 sites in the German Bight area(10).|SOIL: 1,3,5-Trichlorobenzene had an avg soil concentration of 0.026 mg/kg in localities contaminated by agrochemical and communal waste in Slovakia(1).

RURAL/REMOTE: USA, 1,3,5-trichlorobenzene not detected(1).|INDOOR AIR: 1,3,5-Trichlorobenzene was detected in Dutch homes at a max concentration of 5 ug/cu m(1). Indoor data collected from buildings in the Netherlands, Germany, Italy, and USA show 1,3,5-trichlorobenzene levels of <1 ug/cu m in dwellings(2).|SOURCE DOMINATED: 1,3,5-Trichlorobenzene was detected at waste dump atmospheric samples at 16.9 and 36.4 ng/cu m in Sabinanigo, Spain(1).

It has been calculated that 0.288 tons of 1,3,5-trichlorobenzene are released to the soil in southern Ontario every year(1).

Toxicity

LD50 Rat oral 800 mg/kg|LD50 Mouse oral 3550 mg/kg|LD50 Mouse ip 2260 mg/kg

/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.

/Individuals who suffer from/ skin, liver, kidney, or chronic respiratory disease, will be at an increased risk if they are exposed to chlorobenzenes. /Chlorobenzenes/

1,3,5-Trichlorobenzene's former production and use as a solvent, emulsifier and chemical intermediate(1) may have resulted in its release to the environment through various waste streams(SRC).

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).

The rate constant for the vapor-phase reaction of 1,3,5-trichlorobenzene with photochemically-produced hydroxyl radicals has been estimated as 6.8X10-13 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 24 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 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(2). 1,3,5-Trichlorobenzene has been shown to be susceptible to direct photolysis by sunlight(3).

933.25|BCFs of 600-1,600 and 150-1,700 were measured in carp exposed for a 6 week incubation period at concns of 25 and 2.5 ug/L of 1,3,5-trichlorobenzene, respectively(1). Trout exposed to 1,3,5-trichlorobenzene for up to 119 days had a mean BCF of 1,800(2). Guppy (Poecilia reticulata) had a BCF of 756 wet weight but was calculated as 14,000 based on lipid weight for 1,3,5-trichlorobenzene(3). According to a classification scheme(4), these BCF values suggest that bioconcentration in aquatic organisms is high to very high. 1,3,5-Trichlorobenzene had a measured BCF of 2 in pond snail (Lymnaea stagnalis) after 10 days of exposure(5).|Oligochaete worms, mainly Limnodrilus hoffmeisteri and Tubifex tubifex, were exposed to ... contaminated sediments from Lake Ontario (USA, Canada) for 110 days in laboratory aquariums. The worms accumulated many of the 24 chlorinated chemicals /including 1,3,5-trichlorobenzene/ and for most compounds, concn factors (CF) continued to increase over the 110 day study period. The mixture of chemicals found in the worms differed considerably from that in sediments because of large variations in concentration factors between chemicals.

707.95 L/kg|Measured log Koc values for 1,3,5-trichlorobenzene of 2.8(1), 3.09(2), 3.2(3), 3.69(4), 3.79(5) and 3.82(6), were reported in soil. According to a recommended classification scheme(7), these Koc values suggest that 1,3,5-trichlorobenzene has low to no mobility in soil(SRC).|A log Koc value of 3.6 was measured for 1,3,5-trichlorobenzene in sediment obtained from Ise Bay, Japan(1). A log Koc value of 4.5 was measured from sediment of Lake Ketelmeer, Netherlands(2). Log Koc values of 5.96 and 5.36 were also measured in Lake Ketelmeer at 0-30 cm (3.75% organic matter) and 40-120 cm (6.48% organic matter), respectively(3).

The Henry's Law constant for 1,3,5-trichlorobenzene is 1.89X10-3 atm-cu m/mole(1). This Henry's Law constant indicates that 1,3,5-trichlorobenzene is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 4.6 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 5.5 days(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(3). 1,3,5-Trichlorobenzene's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). 1,3,5-Trichlorobenzene is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.24 mm Hg(1).

GROUND WATER: 1,3,5-Trichlorobenzene had an average ground water concentration of 0.003 ug/L in localities contaminated by agrochemical and communal waste in Slovakia(1).|SURFACE WATER: 1,3,5-Trichlorobenzene was detected at mean concns of 0.04 ng/L at Edwards Point and 0.06 ng/L at Port Lambton in Ontario, Canada(1). 1,3,5-Trichlorobenzene was detected at concns of 0.016, 0.022 and 0.028 ng/L in Lake Ontario near Toronto, Canada(2). 1,3,5-Trichlorobenzene was detected in 33% of samples taken from 21 stations in Lake Erie in 1986 at concns of not detected to 0.08 ng/L (detection limit 0.004 ng/L)(3). 1,3,5-Trichlorobenzene was detected at the survey stations of Zollenspieker at 0.8-4.3 ng/L in all 12 samples and Seemannshoft at 0.7-3.7 ng/L in all 12 samples, on the River Elbe, near Hamburg, Germany in 1992(4). 1,3,5-Trichlorobenzene was detected at <1, <1, <0.1, and <0.2% of the total chlorobenzenes found in samples from Aire, Calder, Don, and Trent Rivers, Humber, respectively, samples were taken Feb 1995 to Feb 1997(5). Dutch surface water samples taken from 1992 to 1997 from the Rhine, Meuse, northern delta area, and Westerscheld were reported as <0.1 ug/L of 1,3,5-trichlorobenzene(6). 1,3,5-Trichlorobenzene had an avg surface water concn of 0.003 ug/L in localities contaminated by agrochemical and communal waste in Slovakia(7). 1,3,5-Trichlorobenzene was detected at concns of 0.04-0.11 ug/L in Lake Ketelmeer, Netherlands(8). A 1,3,5-trichlorobenzene concn of 0.4 ug/L was found in the Rhine River at Lobith, Netherlands in July 1979(9).|SEAWATER: Southern North Sea samples from the Rhine/Meuse Estuary taken Aug 1983 to Jul 1984 had 1,3,5-trichlorobenzene concentrations of <0.2-4 parts per trillion with a median concentration of 0.6 parts per trillion(1). 1,3,5-Trichlorobenzene was detected at concns of <1 ng/L to 153 ng/L(2) and 0-0.13 ug/L(3) in the Forth Estuary, England. 1,3,5-Trichlorobenzene was detected at concentrations of 0-53.4 ng/L in Ise Bay, Japan(4).|RAIN/SNOW: 1,3,5-Trichlorobenzene was identified at 1 of 10 snow sample sites in Russia and Finland; 0.73 ug/kg at Moscow State University (Moscow, Russia)(1).|Ten chlorobenzenes /including 1,3,5-trichlorobenzene/, hexachlorobutadiene and (polychlorinated biphenyls) were measured in Niagara River water and suspended solids, and in western Lake Ontario sediments and benthic fauna. High levels of these contaminants were found on all fractions of the river suspended solids, but the larger particles contained higher concn. A portion of the chlorobenzenes, hexachlorobutadiene and polychlorinated biphenyls present in the lake sediments was available to benthic organisms. ...

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).

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).

Occupational exposure to 1,3,5-trichlorobenzene may occur through inhalation and dermal contact with this compound at workplaces where 1,3,5-trichlorobenzene is produced or used. Monitoring data indicate that the general population may be exposed to 1,3,5-trichlorobenzene via inhalation of ambient air and ingestion of food. (SRC)|In a study of aerial fallout in Southern California (Spring 1976), five sampling sites showed median inhalation levels of less than 6 ng/sq m/day.

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).

Drug Information

... 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.

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.

15.49 Days|Approximate half-life of 1,3,5-trichlorobenzene is 8.5 days.

SYMPTOMS: Symptoms of exposure to this compound include skin, eye and mucous membrane irritation; and hair loss. ACUTE/CHRONIC HAZARDS: This compound may cause skin, eye and mucous membrane irritation. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)


Fresh air, rest. Refer for medical attention.


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


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

Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Aromatic hydrocarbons and related compounds/|Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aromatic hydrocarbons and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Consider drug therapy for pulmonary edema ... . Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... .Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aromatic hydrocarbons and related compounds/

1,3,5-trichlorobenzene

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

Cough. Sore throat.


Redness. Pain.

1,3,5-Trichlorobenzene Use and Manufacturing

Methods of Manufacturing

... 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.

Uses

1,3,5-Trichlorobenzene is an organochlorine compound. It is one of the three isomers of trichlorobenzene. Being more symmetrical than the other isomers, it exists as colourless crystals whereas the other isomers are liquids at room temperature.It is not formed upon chlorination of benzene. Instead it is prepared by the Sandmeyer reaction from 3,5-dichloroaniline.


Propellants and blowing agents

Production

< 25,000 lb|(1972) Not produced commercially in US|(1975) Not produced commercially in US

Explosives manufacturing|Benzene, 1,3,5-trichloro-: ACTIVE|TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.

Method: EPA 8121; Procedure: gas chromatography; Analyte: 1,3,5-trichlorobenzene; Matrix: environmental samples and RCRA wastes; Detection Limit: 12 nanogram/L.|Air Samples: ... An air sampling tube packed with two sections of Amberlite XAD-2 resin separated by a silanized glass wool plug, to collect the chlorobenzenes /is used/. The adsorbent is desorbed with carbon tetrachloride and analyzed by GC using a photoionization detector. When using this method the minimum detection limits for mono, di, tri, tetra, and pentachlorobenzenes are 15, 20, 30, 35, and 45 ppb (v/v), respectively. /Chlorobenzenes/|A Soxhlet extraction technique for recovering chlorobenzenes from sediments and fish was described. Extract was concentrated by evaporation, cleaned with florisil (sediments) or a combination of alumina, silica gel, florisil & acidified silica gel (fish) before quantitation by capillary gas chromatography with an electron capture detector. Recoveries for all chlorobenzenes were greater than 80%. /Chlorobenzenes/|... Because of differences in the electron capture response of the isomers at each chlorination level, residue quantitation requires the separation of all 12 chlorobenzenes. Resolution studies were made on packed and capillary columns coated with Kovats' Ca87H176 hydrocarbon, OV-101, OV-210, OV-17 and Carbowax 20M. Satisfactory resolution of all 12 chlorobenzenes was obtained with a Carbowax 20M-coated 20 ml column operated isothermally at 120 °C. /Chlorobenzenes/|For more Analytic Laboratory Methods (Complete) data for 1,3,5-TRICHLOROBENZENE (10 total), please visit the HSDB record page.

Determination of chlorobenzenes in human urine and blood samples by gas chromatography with photoionization detection. The method consisted of carbon tetrachloride extraction, silica gel column chromatography, and concn with a Kuderna-Danish concentrator. Specially designed column packing allowed separation in 16 min. Recoveries from urine and blood samples were 83% (1 to 500 ppb). /chlorobenzenes/|Bonded phase packed columns were investigated for their utility in determining a variety of chemicals, drugs and pesticides by gas chromatography/mass spectrometry. Combined with a generalized extraction procedure and clean-up by gel permeation chromatography, the procedure enabled development of a single screen applicable to the biological matrices encountered in veterinary toxicology.|A method has been developed for determination of organochlorine contaminants in human adipose tissue. After fat extraction from the tissue with acetone-hexane (15 + 85, v/v), organochlorines were fractionated from fat by gel permeation chromatography with methylene chloride-cyclohexane (1 + 1, v/v) as solvent. After Florisil column cleanup, the GPC extract was analyzed by capillary column gas chromatography using 2 columns of different polarity. Compound identity was confirmed by gas chromatography-mass spectrometry using selected ion monitoring. Recoveries for fortification levels of 10-500 ng/g were greater than 80% except for trichlorobenzene and hexachlorobutadiene (ca 60%). /Trichlorobenzene/|A 10 g biological sample was treated with 5% sodium hydroxide (100 ml), extracted with distilled water in the presence of 5 ml n-hexane, and the extract allowed to stand for cooling. The org phase was separated, treated with 5 ml concentrated hydrogen sulfate (for removal of interfering substances), 10 ml sodium sulfate (10%), 10 ml distilled water, then anhydrous sodium sulfate (for dehydration), and analyzed for chlorobenzenes by gas chromatography. Recoveries ranged from 90.2 to 95.2%. Reproducibility with a relative standard deviation of < 2% was found. In general, detection limits increased with increasing chloride contents. The method was used in detection of chlorobenzene contamination in fish. /Chlorobenzenes/|Complex sample matrixes of estuarine biota tissue were analyzed for selected chlorinated cmpd /including 1,3,5-trichlorobenzene/ using gas chromatography/positive chemical ionization/tandem mass spectrometry. The detection limit ... was 20 pg, and the instrument response was linear over 5 orders of magnitude.

Computed Properties

Molecular Weight:181.4
XLogP3:4.2
Exact Mass:179.930033
Monoisotopic Mass:179.930033
Heavy Atom Count:9
Complexity:63.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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