1,2,4,5-Tetrachlorobenzene

HCID 7270

Basic information

CAS
12408-10-5
Standard SMILES
Clc1cc(Cl)c(Cl)cc1Cl
InChIKey
JHBKHLUZVFWLAG-UHFFFAOYSA-N
Molecular formula
C6H2Cl4
Average molar mass
215.9 g/mol
Monoisotopic mass
213.89106078

Overview

1,2,4,5-tetrachlorobenzene appears as odorless white flakes or chunky solid. (NTP, 1992)

Names & identifiers

Preferred name
1,2,4,5-Tetrachlorobenzene
IUPAC
1,2,4,5-tetrachlorobenzene
English name
1,2,4,5-Tetrachlorobenzene
Molecular formula
C6H2Cl4
Molecular weight
215.89

Names & synonyms

1,2,4,5-TETRACHLOROBENZENE95-94-3s-TetrachlorobenzeneBenzene, 1,2,4,5-tetrachloro-Benzene tetrachloride1,2,4,5-TetrachlorbenzolDTXSID70243205N27529KGHNSC-27003DTXCID604320CHEBI:36697RefChem:71462
Show more names
1,2,4,5-tcb1.2.4.5-TetracTETRACHLOROBENZOLrcrawastenumberu207ethenyl trichloridebenzenetetrachloride1,2,4,5-TetrachlorobPurity(GC) min. 99.0 %
202-466-2RCRA waste number U207MFCD0000054963697-22-3CAS-95-94-3CCRIS 766UNII-5N27529KGHHSDB 2733

Database identifiers

CAS
12408-10-5、63697-22-3、95-94-3
PubChem CID
7270
DTXSID
DTXSID7024320
ChEMBL
CHEMBL45428
ChEBI
CHEBI:36697
UNII
5N27529KGH
EC Number
202-466-2
Nikkaji
J3.573D

Properties

Computed structural properties

XLogP
4.6
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
0
Heavy atoms
10

Experimental & physicochemical properties

SolventsSolvents -> Chlorinated Aromatics
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
PesticidesPesticide -> EPA IRIS
LogP · 3 items

Log Kow= 4.60

4.9

4.6

OdorSTRONG, UNPLEASANT ODOR
Density · 5 items

1.858 at 70 °F (NTP, 1992) - Denser than water; will sink

1.833 kg/l

Heat of fusion: 112.2 J/g; heat capacity for liquid: 1.142 J/g; critical density: 0.475 kg/l

1.83 g/cm³

1.858 @ 22°C

Physicochemical properties

Melting point
139 °C · 139 °C
Boiling point
240 · 240-246 °C(lit.)
Density
1.858 · 1.858
vapor pressure
5 at · 5 at 25 °C (extrapolated, Mackay et al., 1982)
refractive index
1.5348 · 1.5348 (estimate)
Flash point
230 °F · >230 °F

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 1.1% (1 of 94) of reports.

Warning

H302 (98.9%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, 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 94 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

Hazard information

Regulatory Information · 3 items

Hazard Traits - Bioaccumulation; Environmental Persistence

S - indicates a substance that is identified in a final Significant New Use Rule.

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

DOT LabelClass 9
Fire Hazards · 2 items

This chemical is combustible. (NTP, 1992)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Risk of fire and explosion on contact with oxidizing agents.

Fire PotentialCombustible when exposed to heat or flame.
Health HazardsSYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes, mucous membranes and upper respiratory tract.
Hazards Summary · 1 item

If burned, toxic fumes include hydrogen chloride and phosgene; Chronic feeding studies of animals show evidence of damage to liver, kidneys, lungs, and thyroid gland; LD50 (oral, rat, male) = 3105 mg/kg; At lethal doses, animals have CNS depression, diarrhea, and coma; [CHEMINFO]

Safety & protection

Fire Fighting · 2 items

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

Use powder, carbon dioxide.

First Aid Measures · 4 items

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. Refer for medical attention .

First Aid · 1 item

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.

Safe StorageSeparated from strong oxidants.
Fire Fighting Procedures/USE/ CARBON DIOXIDE /&/ DRY CHEMICAL.
Cleanup Methods · 3 items

Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ 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. /Chlorobenzene/

Environmental considerations: Water spill: Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. If dissolved, in region of 10 ppm or greater concn, 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. /Chlorobenzene/

Environmental considerations: Air spill: Apply water spray or mist to knock down vapors. Combustion products include corrosive or toxic vapors. /Chlorobenzene/

Toxicology

Body Burden · 2 items

Unidentified tetrachlorobenzene isomer(s) were found in human blood samples taken from a resident in the area of the Love Canal at a concentration of 2.6 ng/ml(1). Concentrations of 0.008 to 0.039 ug/g 1,2,4,5-tetrachlorobenzene were detected in human adipose tissue in Japan(2). Mean concentrations of 0.016 ug/g were detected in Yugoslavian human adipose tissue and 2 ug/kg in human milk, respectively(3).

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(1). 1,2,4,5-Tetrachlorobenzene was identified, not quantified, in the adipose tissue of non-occupationally exposed individuals in Germany(2).

Target OrgansUrinary
Ecotoxicity Values · 3 items

LC50 Bluegill (sunfish) 5.69 mg/l/24 hr; 4.35 mg/l/48 hr; 1.55 mg/l/96 hr /Conditions of bioassay not specified/

LC50 Sheepshead minnow > 1.80 mg/l/24 hr; 0.90 mg/l/48 hr /Conditions of bioassay not specified/

LC50 Guppy (Poecilia reticulata) 0.30 ppm/14 days /Conditions of bioassay not specified/

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a recommended classification scheme(1), and log Koc values in the range of 3.2-3.9(2-4), 1,2,4,5-tetrachlorobenzene is expected to have low mobility in soil(SRC). Volatilization of 1,2,4,5-tetrachlorobenzene is expected from moist soil surfaces(SRC) given its Henry's Law constant of 1.0X10-3 atm-cu m/mole at 20 °C(5), but adsorption may attenuate this process(SRC). Volatilization of 1,2,4,5-tetrachlorobenzene from dry soil surfaces is not expected(SRC) based on a vapor pressure of 0.005 mm Hg at 25 °C(5). Biodegradation is expected to occur slowly based on a half-life of 47 days in a sewage sludge ammended soil(6).

AQUATIC FATE: Based on a recommended classification scheme(1), and log Koc values in the range of 3.2-3.9(2-4), 1,2,4,5-tetrachlorobenzene is expected to adsorb to suspended solids and sediments in water(SRC). 1,2,4,5-Tetrachlorobenzene is expected to volatilize from water surfaces(5,SRC) given its Henry's Law constant of 1.0X10-3 atm-cu m/mole at 20 °C(6), but adsorption may attenuate this process(SRC). Estimated volatilization half-lives for a model river and model lake are 6 and 150 hours, respectively when neglecting adsorption(5,SRC). The volatilization half-life in a model pond is approximately 34 days when adsorption is considered(7). According to a classification scheme(8), BCF values in the range of 1,600 to 4,800, measured in carp(9) and log BCF values of 3.7-4.1 measured in trout(10), suggest that bioconcentration in aquatic organisms is high(SRC). Biodegradation is expected to occur slowly based on a half-life of 29 days measured in anaerobic river sediment(11). When irradiated with light greater than 285 nm, this compound was degraded 61 percent in a water solution in 16 hrs(12), 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), 1,2,4,5-tetrachlorobenzene, which has a vapor pressure of 0.005 mm Hg at 25 °C(2), is expected to exist in the vapor phase in the ambient atmosphere. Vapor-phase 1,2,4,5-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 200 days(SRC) from its estimated rate constant of 8.2X10-14 cu cm/mole-sec(3).

Food Survey Values · 1 item

1,2,4,5-Tetrachlorobenzene was detected in potatoes (0.486 and 2.19 mg/kg) and lettuce (0.012 mg/kg)(1). Combined 1,2,3,5- and 1,2,4,5-tetrachlorobenzene 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). 1,2,4,5-Tetrachlorobenzene was detected in meat from Yugoslavia at a concn of 1.8 ng/g(3).

Adverse EffectsNeurotoxin - Acute solvent syndrome

Regulatory information

RCRA Requirements · 1 item

U207; As stipulated in 40 CFR 261.33, when 1,2,4,5-tetrachlorobenzene, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

TSCA Requirements · 1 item

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. 1,2,4,5-Tetrachlorobenzene is included on this list.

CERCLA Reportable Quantities · 1 item

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 5000 lb or 2270 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

Clean Water Act RequirementsToxic pollutant designated pursuant to section 307(a)(1) of the Clean Water Act and is subject to effluent limitations. /Chlorinated benzenes/
State Drinking Water Guidelines · 2 items

(AZ) ARIZONA 2 ug/l

(FL) FLORIDA 4 ug/l

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
DB9450000
ridadr
UN 3077 9/PG 3
hs_code
29036990

Chemistry & industry

Pharmacology

Biological Half-LifeAT END OF 2 YR EXPOSURE AT 5 MG/KG/DAY IN DIET OF DOGS, 1,2,4,5-TETRACHLOROBENZENE WAS ELIMINATED FROM FAT & PLASMA WITH HALF-LIFE OF 111 & 104 DAYS.
Metabolism/Metabolites · 5 items

... /IN URINE FROM RATS DOSED/ WITH TOTAL OF 300 MG/KG OF HEXACHLOROBENZENE FOR 10 MONTHS ... 1,2,4,5-TETRACHLOROBENZENE & CERTAIN OTHER CHLOROBENZENES WERE DETECTED, BUT NOT COMPLETELY IDENTIFIED.

ORAL ADMIN OF 100 MG/KG HEXACHLOROBENZENE TO RATS TWICE/WK PRODUCED 1,2,3,4-TETRACHLOROBENZENE IN URINE & 1,2,4,5-TETRACHLOROBENZENE IN FECES.

1,2,4,5-TETRACHLOROBENZENE IS METABOLIZED TO 2,3,5,6-TETRACHLOROPHENOL IN RABBITS. /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 1,2,4,5-TETRACHLOROBENZENE (8 total), please visit the HSDB record page.

Absorption, Distribution and Excretion · 5 items

1,2,4,5-TETRACHLOROBENZENE ACCUM IN ADIPOSE TISSUE FOLLOWING CONTINUOUS ADMIN WITH FOOD TO RATS.

AT END OF 2 YR EXPOSURE AT 5 MG/KG/DAY IN DIET OF DOGS, 1,2,4,5-TETRACHLOROBENZENE REACHED 98 & 97% OF CALCULATED STEADY STATE CONCN IN FAT & PLASMA. IT WAS ELIMINATED FROM FAT & PLASMA WITH HALF-LIFE OF 111 & 104 DAYS. RATE OF ELIMINATION RESULTED IN DRAMATIC CHANGES IN FAT/PLASMA RATIO.

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.

... This study was designed to determine the subchronic toxicity of the tetrachlorobenzenes. Results indicated that 1,2,4,5-tetrachlorobenzene accumulated in fat and liver in a dose dependent manner.

THE MEAN LEVELS OF CHLOROBENZENES (INCLUDING 1,2,4,5-TETRACHLOROBENZENE) IN HUMAN MILK AND ADIPOSE TISSUE WERE DETERMINED AND RANGED FROM TRACES TO 25 UG/KG FOR HUMAN MILK AND FROM NOT DETECTED TO 146 UG/KG FOR ADIPOSE TISSUE. THE DISTRIBUTION OF DIFFERENT CHLOROBENZENE ISOMERS IN ADIPOSE TISSUE AND MILK WAS DIFFERENT.

Uses & manufacturing

Uses · 4 items

Used in the synthesis of other organic compounds; [HSDB]

IN SYNTH OF 2,4,5-TRICHLOROPHENATE SODIUM

Int for herbicides & defoliants /former use/; insecticide /former use/; impregnant for moisture resistance; electrical insulation

USED IN THE PRODUCTION OF 2,4,5-TRICHLOROPHENOL /FORMER USE/

U.S. Imports(1983) 1.60X10+6 g
Methods of Manufacturing · 2 items

... MANUFACTURED ... /BY/ THE CHLORINATION OF BENZENE WITH 4 MOLES OF CHLORINE ...

Iodine plus antimony trichloride is effective in selectively chlorinating 1,2,4-trichlorobenzene to 1,2,4,5-tetrachlorobenzene.

Formulations/PreparationsTECHNICAL GRADE /HEXACHLOROBENZENE/ USED IN AGRIC CONTAINS 98% HEXACHLOROBENZENE, 1.8% PENTACHLOROBENZENE, & 0.2% 1,2,4,5-TETRACHLOROBENZENE. /HEXACHLOROBENZENE/
General Manufacturing Information · 2 items

Benzene, 1,2,4,5-tetrachloro-: ACTIVE

Distillation range: 240-246 °C

Applications

UsesIntermediate for herbicides and defoliants, insecticide, impregnant for moisture resistance, electrical insulation.

Uses1,2,4,5-Tetrachlorobenzene was used to study the environmental behavior of hexachlorobutadiene (HCBD).

Additional notes

DefinitionChEBI: A tetrachlorobenzene carrying chloro groups at positions 1, 2, 4 and 5.

Related reactions

9 records

Compound notes

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