1,2,3,5-Tetrachlorobenzene
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1,2,3,5-Tetrachlorobenzene
structure -
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CAS No:
634-90-2
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Formula:
C6H2Cl4
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Chemical Name:
1,2,3,5-Tetrachlorobenzene
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Synonyms:
Benzene,1,2,3,5-tetrachloro-;1,2,3,5-Tetrachlorobenzene;1,2,4,6-Tetrachlorobenzene;NSC 78934
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CAS No:
Description
ChEBI: A tetrachlorobenzene carrying chloro groups at positions 1, 2, 3 and 5.
1,2,3,5-tetrachlorobenzene appears as white crystals or off-white solid. (NTP, 1992)
1,2,3,5-tetrachlorobenzene appears as white crystals or off-white solid. (NTP, 1992)|1,2,3,5-tetrachlorobenzene is a tetrachlorobenzene carrying chloro groups at positions 1, 2, 3 and 5.
1,2,3,5-Tetrachlorobenzene Basic Attributes
215.89
215.89
211-217-7
I27N186CIN
78934
DTXSID1026089
Colorless needles
2903999090
Characteristics
0
4.66
1,2,3,5-tetrachlorobenzene appears as white crystals or off-white solid. (NTP, 1992)
1.6±0.1 g/cm3
51 °C
246 °C
113 °C
1.583
In water, 5.1 mg/l at 25 deg C.
APPROX 4°C
0.07 at 25 °C (extrapolated, Mackay et al., 1982)
Oral-rat LD50: 1727 mg/kg
Open flame is flammable; burning releases toxic chloride fumes
0.00 atm-m3/mole|Henry's Law constant= 1.6X10-3 atm-cu m/mol at 25 °C
DISTILLATION RANGE 240-246 °C
Insoluble in water.
Aryl Halides
Simple aromatic halogenated organic compounds, such as 1,2,3,5-TETRACHLOROBENZENE, are very unreactive. Halogenated organics generally become less reactive as more of their hydrogen atoms are replaced with halogen atoms. Materials in this group may be incompatible with strong oxidizing and reducing agents. Also, they may be incompatible with many amines, nitrides, azo/diazo compounds, alkali metals, and epoxides. This chemical may react with oxidizers. (NTP, 1992).
Safety Information
UN12303/PG2
3
22-39/23/24/25-23/24/25-11
22-24/25-45-36/37-16-7
DB9445000
Xn,T,F
Treasury is ventilated at low temperature and dry; stored separately from oxidants and food additives
P260-P280-P301 + P310-P311
H301 + H311 + H331-H370
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.
IN MFR OF SODIUM SALT OF TRICHLOROPHENOL, SODIUM HYDROXIDE, METHYL ALCOHOL & TETRACHLOROBENZENE WERE HEATED. DURING HEATING PROCESS, PRESSURE SUDDENLY INCR RAPIDLY & EXPLOSION OCCURRED. /TETRACHLORBENZENE/
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
UN 1230 3/PG 2
This chemical is probably combustible. (NTP, 1992)
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P301+P312, P330, P391, and P501|Aggregated GHS information provided by 43 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]|P273, P391, and P501
Fires involving this compound can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and 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 absorbent 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 chemical under refrigerated temperatures, and keep it away from oxidizing materials. 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)
Combined tetrachlorobenzene isomers were detected at concns of 38-1,800,000 ng/cu m in the effluent of a waste gasification and combustion pilot plant(1) and detected at concns of 74.7 and 48 ng/cu m in the effluent of a hazardous waste incinerator in Biebesheim, Germany(2). 1,2,3,5-Tetrachlorobenzene was identified, not quantified, in the effluent from a coal-fired power plant(3). 1,2,3,5-Tetrachlorobenzene was detected at a concn of 0.3 ug/cu m in the effluent of a hazardous waste incinerator in Germany(4). Combined tetrachlorobenzene isomers were detected at concns of 0.01-0.11 ug/l in the effluent of 2 Dow Chemical plants near the St. Claire River, Canada(5). 1,2,3,5-Tetrachlorobenzene was identified, not quantified, in pulp mill effluents in Canada(6). Combined tetrachlorobenzene isomers were detected at concns of 29 and 57 ug/cu m in the effluent of municipal refuse incinerators located in Virginia and Ohio, respectively(7).
1,2,3,5-Tetrachlorobenzene was detected in the sediment of Lake Ketelmeer, Netherlands at concns of 4 and 2 ng/kg(1). Mean 1,2,3,5-tetrachlorobenzene concns of 0.1, 0.4, 0.3 and 6 ppb were detected in the superficial sediments from Lakes Superior, Huron, Erie, and Ontario, respectively(2). Combined 1,2,3,5- and 1,2,4,5-tetrachlorobenzene were detected at concns of 0-0.4 ng/g in sediment from Ise Bay, Japan(3). 1,2,3,5-Tetrachlorobenzene was detected at a max concn of 3 ng/g in sediment taken from the Scheldt estuary, Netherlands(4). Combined 1,2,3,5- and 1,2,4,5-tetrachlorobenzene was detected in soil samples in Niagara Falls, NY at mean concns of 910, 4,620, 2,000, 1,300 and 290 pg/g(5). Sediment from the St Lawrence River contained 1,2,3,5-tetrachlorobenzene at concns of 0.39-1.6 ng/g(6). Soil from Hengelo, Netherlands contained 1,2,3,5-tetrachlorobenzene at a mean concn of 1.61 mg/kg(7). 1,2,3,5-Tetrachlorobenzene was detected in sediment (6.6 ng/g) and suspended particulate matter (1.9 ng/g) in Lake Ontario(8). Combined 1,2,3,5- and 1,2,4,5-tetrachlorobenzene isomers were detected in sediment off the coast of Taiwan at concns of 1-12 ng/g(9).
URBAN/SUBURBAN: Combined 1,2,3,5- and 1,2,4,5-tetrachlorobenzene isomers were detected in the air of Hamburg, Germany at concns of 0.5-20.9 ng/cu m(1). Combined tetrachlorobenzene isomers were detected at mean concns of 690 parts per trillion in the urban air of the US and 95 parts per trillion in source dominated air(2). Combined tetrachlorobenzne isomers were detected in the ambient air of Niagara Falls, NY at trace levels to 451 ng/cu m(3).
Toxicity
moderately toxic
Since TeCB's can increase cytochrome p450 levels, ... it appears to induce metabolic enzymes. /This/ induction of microsomal enzyme activity has been shown to enhance the metabolism of a wide variety of drugs, pesticides and other xenobiotics. Exposure to TeCB could therefore result in decreased pharmacologic and/or toxicologic activity of numerous compounds. /In the event/ that chemical agents are metabolized to more active or toxic reactive intermediates ... exposure to TeCB would result in enhanced activity and/or toxicity of these agents. /Tetrachlorobenzenes/
LD50 Rats oral 1727 mg/kg|TDLo Rats oral 2mg/kg (6-15 days preg), Toxic Effects: Reproductive fertility.
/Individuals who suffer from/ skin, liver, kidney or chronic respiratory disease, will be at an increased risk if they are exposed to chlorobenzenes. /Chlorobenzenes/
1,2,3,5-Tetrachlorobenzene's production and use as a starting material and inermediate for herbicides and defoliants may result in its release to the environment through various waste streams(1,SRC). 1,2,3,5-Tetrachlorobenzene is a degradation byproduct of pentachlorobenzene and hexachlorobenzene and therefore may enter the environment as a result of the microbial degradation of these compounds(2,SRC).
TERRESTRIAL FATE: Based on a recommended classification scheme(1), and log Koc values in the range of 3.2-4.2(2,3), 1,2,3,5-tetrachlorobenzene is expected to have low mobility in soil(SRC). Volatilization of 1,2,3,5-tetrachlorobenzene is expected from moist soil surfaces given its Henry's Law constant of 1.6X10-3 atm-cu m/mole at 25 °C(4), but adsorption may attenuate this process(SRC). Volatilization of 1,2,3,5-tetrachlorobenzene from dry soil surfaces is not expected(SRC) based on a vapor pressure of 0.07 mm Hg at 25 °C(4). A half-life of 45 days in sewage sludge amended soil suggests that biodegradation of 1,2,3,5-tetrachlorobenzene will be slow(5).|AQUATIC FATE: Based on a recommended classification scheme(1), and a log Koc value of 3.9(2) measured in sediment, 1,2,3,5-tetrachlorobenzene is expected to adsorb to suspended solids and sediment in water(SRC). 1,2,3,5-Tetrachlorobenzene is expected to volatilize from water surfaces(3,SRC) given its Henry's Law constant of 1.6X10-3 atm-cu m/mole at 25 °C(4), but adsorption may attenuate this process(SRC). Estimated volatilization half-lives for a model river and model lake are 5 and 150 hours, respectively when neglecting adsorption(3,SRC). The volatilization half-life from a model pond is 36 days when adsorption is considered(5). According to a classification scheme(6), BCF values in the range of 1,300 to 3,600 measured in fish(7-9), suggest that bioconcentration in aquatic organisms is high(SRC). A half-life of 19 days in an acclimated anaerobic sediment slurry suggests that biodegradation of 1,2,3,5-tetrachlorobenzene will be slow(10). When irradiated with light greater than 285 nm, this compound was degraded 66 percent in 40 hrs in a water solution(11), suggesting that photolysis in surface waters may be important(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,2,3,5-tetrachlorobenzene, which has a vapor pressure of 0.07 mm Hg at 25 °C(2), is expected to exist in the vapor phase in the ambient atmosphere. Vapor-phase 1,2,3,5-tetrachlorobenzene 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 80 days(SRC) from its estimated rate constant of 2.0X10-13 cu cm/molecule-sec at 25 °C(3).
The rate constant for the vapor-phase reaction of 1,2,3,5-tetrachlorobenzene with photochemically-produced hydroxyl radicals has been estimated as 2.0X10-13 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 80 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1,SRC). 1,2,3,5-Tetrachlorobenzene is not expected to undergo hydrolysis in the environment due to the lack of functional groups to hydrolyze(SRC). 1,2,3,5-Tetrachlorobenzene in a water solution irradiated at wavelengths greater than 285 nm was 66 percent photodegraded in 40 hours(2).
3.89e+03|A measured steady state bioconcentration factor of 1800 was obtained for 1,2,3,5-tetrachlorobenzene using bluegill.|Bluegill sunfish exposed to 7.7 ug/l of 1,2,3,5-tetrachlorobenzene for 14-28 days had an avg BCF value of 1,800(1). A BCF value of 3,600 was observed for guppies exposed to 1,2,3,5-tetrachlorobenzene(2) and a BCF value of 1,300 was observed for mosquito fish exposed to 1,2,3,5-tetrachlorobenzene(3). According to a classification scheme(4), these BCF values suggest that bioconcentration in aquatic organisms is high(SRC).
1.58e+03 L/kg|Log Koc values of 4.2(1) and 3.2(2) were reported for 1,2,3,5-tetrachlorobenzene. A log Koc value of 3.9 was measured for 1,2,3,5-tetrachlorobenzene in sediment obtained from Ise Bay, Japan(3) According to a recommended classification scheme(4), these Koc values suggest that 1,2,3,5-tetrachlorobenzene has low mobility in soil(SRC).
The Henry's Law constant for 1,2,3,5-tetrachlorobenzene is 1.6X10-3 atm-cu m/mole at 25 °C(1). This value indicates that 1,2,3,5-tetrachlorobenzene will volatilize from water, but adsorption may attenuate this process(2,SRC). 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) is estimated as approximately 5 hours(2,SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is estimated as approximately 150 hours(2,SRC). The volatilization half-life from a model pond is about 36 days when adsorption is considered(3). 1,2,3,5-Tetrachlorobenzene's Henry's Law constant(1) indicates that volatilization from moist soil surfaces is expected, but adsorption may attenuate this process(SRC). 1,2,3,5-Tetrachlorobenzene is not expected to volatilize from dry soil surfaces(SRC) based on a vapor pressure of 0.07 mm Hg at 25 °C(1).
SURFACE WATER: 1,2,3,5-Tetrachlorobenzene was detected at concns of 0.1-1.4 ng/l in the Niagara River(1). Water collected in the vicinity of an industrial outfall in the Calacasieu River, LA contained 1,2,3,5- and 1,2,4,5-tetrachlorobenzene at a concn of 42 ng/l(2). 1,2,3,5-Tetrachlorobenzene was detected at concns of 0.01 and 0.005 ng/l in Lake Ontario(3). 1,2,3,5-Tetrachlorobenzene was detected at an avg concn of 18 pg/l in Lake Ontario(4) and 0.004 ng/l in Lake Huron(5). Combined isomers of tri- and tetrachlorobenzene were detected in rivers from Slovenia at a mean concn of 80 ng/l(6). 1,2,3,5-Tetrachlorobenzene was detected in the Elbe River, Germany at concns of 0.23-0.84 ng/l(7).|DRINKING WATER: Combined isomers of tetrachlorobenzene were detected in the drinking water of homes near Love Canal, NY at concns of 120-2,000 ng/l(1).
1,2,3,5-Tetrachlorobenzene was detected in carrots (0.0297 ug/kg (peel)) and potatoes (0.0216 ug/kg (peel)) sampled in the UK(1). Combined 1,2,3,5- and 1,2,4,5-tetrachlorobenzene isomers were detected in the following oils: corn (0.04 mg/kg), rape (0.005 mg/kg), sunflower (0.001 mg/kg), peanut (0.001 mg/kg), sesame (0.005 mg/kg) walnut (0.005 mg/kg), hazelnut (0.01 mg/kg) and poppy (0.005 mg/kg)(2).
1,2,3,5-Tetrachlorobenzene was detected in human milk in Canada at 0.03 ng/g (whole milk) and 0.92 ng/g (milk fat)(1).
Occupational exposure to 1,2,3,5-tetrachlorobenzene may be through inhalation and dermal contact with this compound at workplaces where this compound is produced or used. The general population may be exposed to 1,2,3,5-tetrachlorobenzene via inhalation of ambient air and ingestion of food. (SRC)
1,2,3,5-Tetrachlorobenzene has been detected in 13 of 108 samples of human adipose tissue at a mean concn of 30 ng/g(1). Combined trichlorobenzene and tetrachlorobenzene isomers were detected in human adipose tissue in Slovenia at a concn of 60 ng/g and in human hair samples at 40 ng/g(2). 1,2,3,5-Tetrachlorobenzene was identified, not quantified, in the adipose tissue of non-occupationally exposed individuals in Germany(3). 1,2,3,5-Tetrachlorobenzene was detected at an avg concn in human blood of 5.1 ng/g and adipose tissue at 0.41 ng/g(4).
Drug Information
Three tetrachlorobenzene (TCB) congeners (1,2,3,4- 1,2,3,5- and 1,2,4,5-Tetrachlorobenzene were administered daily by gavage to pregnant Sprague-Dawley rats at levels of 50, 100, or 200 mg/kg from day 6-15 of gestation. Residues of all three congeners were found in maternal and fetal tissues but generally the amounts of the 1,2,4,5- isomer were about 100 times higher than the other two.
1,2,3,5-TETRACHLOROBENZENE WAS IDENTIFIED AS METABOLITE OF PENTACHLOROPHENOL.|CANTHATCH WHEAT SEEDS WERE TREATED WITH LINDANE-(14)C (480 PPM) & PLANTED, TOTAL (14)C RESIDUES WERE DETERMINED IN 19-DAY-OLD SEEDLINGS, 1,2,3,5-TETRACHLOROBENZENE WAS IDENTIFIED IN ROOT SAMPLES.|YIELDS 2,3,4,6-TETRACHLOROPHENOL IN RABBIT. /FROM TABLE/|Lindane administered to hen pheasants resulted in tetrachlorobenzene being identified ... as part of the array of metabolites found in eggs and chicks as well as in the body tissues of hens. /Tetrachlorobenzenes/|For more Metabolism/Metabolites (Complete) data for 1,2,3,5-TETRACHLOROBENZENE (7 total), please visit the HSDB record page.
ACUTE/CHRONIC HAZARDS: This compound may cause irritation on contact. (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)
1,2,3,5-tetrachlorobenzene
1,2,3,5-Tetrachlorobenzene Use and Manufacturing
PRODUCED AS BY-PRODUCT IN MFR OF 1,2,4,5-TETRACHLOROBENZENE BY CHLORINATION OF 1,2,4-TRICHLOROBENZENE OVER ALUMINUM AMALGAM; CHLORINATION OF 1,3,5-TRICHLOROBENZENE OVER ALUMINUM AMALGAM|Obtained by chlorination of 1,3,5-trichlorobenzene
Organic Synthesis.
(1977) NOT PRODUCED COMMERCIALLY IN US|(1979) NOT PRODUCED COMMERCIALLY IN US
Benzene, 1,2,3,5-tetrachloro-: ACTIVE
METABOLITES OF LINDANE, INCL 1,2,3,5-TETRACHLORBENZENE, WERE IDENTIFIED IN WHEAT ROOT SAMPLES BY GAS CHROMATOGRAPHY & MASS SPECTROMETRY.|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 is 15, 20, 30, 35 and 45 ppb (v/v), respectively. /Chlorobenzenes/|EPA Method 1625. Semivolatile organic compounds by isotope dilution GCMS.|EPA Method 8121. Determination of chlorinated hydrocarbons by gas chromatography: capillary column technique.
Analysis Methods
| Name | Column Shape | Active Phase(℃) | Retention index | Temperature Control | Method | Comments | Reference |
|---|---|---|---|---|---|---|---|
| Kovats' RI, non-polar column, isothermal | Capillary | HP-5 | 1338.2 | 120. | isothermal | Santiuste, J.M.Harangi, J.Takács, J.M.Mosaic increments for predicting the gas chromatographic retention data of the chlorobenzenesJ. Chromatogr. A2003, 1002, 1-2, 155-168. | |
| Kovats' RI, non-polar column, isothermal | Capillary | HP-5 | 1338.2 | 120. | isothermal | 60. m/0.25 mm/0.25 μm, N2 | Santiuste J.M.Takacs J.M.Relationships between retention data of benzene and chlorobenzenes with their physico-chemical properties and topological indicesChromatographia2003, 58, 87-96. |
| Kovats' RI, non-polar column, isothermal | Capillary | HP-5 | 1353.8 | 140. | isothermal | 60. m/0.25 mm/0.25 μm, N2 | Santiuste J.M.Takacs J.M.Relationships between retention data of benzene and chlorobenzenes with their physico-chemical properties and topological indicesChromatographia2003, 58, 87-96. |
| Kovats' RI, non-polar column, isothermal | Capillary | SPB-1 | 1331. | 140. | isothermal | 30. m/0.32 mm/0.25 μm | Vezzani, S.Bertocchi, A.Moretti, P.Castello, G.Prediction of the gas chromatographic retention values of chlorobenzenes on different station phases by using structure-retention correlationsJ. Chromatogr. A1998, 803, 1-2, 211-218. |
| Kovats' RI, non-polar column, isothermal | Capillary | DB-5 | 1331.36 | 110. | isothermal | 30. m/0.53 mm/1.5 μm, N2 | Gerbino, T.C.Garbarino, G.Petit-Bon, P.Programmed temperature retention indices: calculation of linear programmed temperature retention indices of halogenated benzenes from isothermal dataAnn. Chim. (Rome)1996, 86, 63-75. |
Computed Properties
Molecular Weight:215.9
XLogP3:4.7
Exact Mass:215.888111
Monoisotopic Mass:213.891061
Heavy Atom Count:10
Complexity:104
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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