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2,3',4,4',5,5'-Hexachlorobiphenyl

HCID 40479
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Basic information

CAS
52663-72-6
Standard SMILES
Clc1cc(Cl)c(-c2cc(Cl)c(Cl)c(Cl)c2)cc1Cl
InChIKey
AZXHAWRMEPZSSV-UHFFFAOYSA-N
Molecular formula
C12H4Cl6
Average molar mass
360.9 g/mol
Monoisotopic mass
357.844416

Overview

2,3',4,4',5,5'-Hexachlorobiphenyl is a trichlorobenzene and a hexachlorobiphenyl.

Names & identifiers

Preferred name
2,3',4,4',5,5'-Hexachlorobiphenyl
IUPAC
1,2,3-trichloro-5-(2,4,5-trichlorophenyl)benzene
English name
2,3',4,4',5,5'-Hexachlorobiphenyl
Molecular formula
C12H4Cl6
Molecular weight
360.88

Names & synonyms

2,3',4,4',5,5'-Hexachlorobiphenyl52663-72-6PCB 1672,3',4,4',5,5'-Hexachloro-1,1'-biphenylHD4MZI40CH1,1'-Biphenyl, 2,3',4,4',5,5'-hexachloro-DTXSID70741652,4,5,3',4',5'-HEXACHLOROBIPHENYLRefChem:53532DTXCID80412441,2,4-trichloro-5-(3,4,5-trichlorophenyl)benzenePCB No. 167
Show more names
CB-167PCB-167BZ NO 167PCB NO 167234455HXCBC20016700 PCB No. 167PCB No. 167 in CyclohexanePhloroglucinol Impurity 1241,1'-BIPHENYL,2,3',4,4',5,5'-3,3',4,4',5,6'-Hexachlorobiphenyl
1,2,3-trichloro-5-(2,4,5-trichlorophenyl)benzeneCHEMBL13615123'44'55'-HexachlorobiphenylHSDB 3947UNII-HD4MZI40CHAZXHAWRMEPZSSV-UHFFFAOYSA-NSCHEMBL2281805SCHEMBL29944597

Database identifiers

CAS
52663-72-6

Properties

Computed structural properties

XLogP
7.5
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
1
Heavy atoms
18
Formal charge
0
Complexity
274

Experimental & physicochemical properties

PolymersOther Classes -> Halogenated Polyaromatics
LogP6.82
SolubilitySolubility in water is extremely low. ... Soluble in oils and organic solvents.
Endocrine DisruptorsPotential endocrine disrupting compound
Vapor Pressure0.00000058 [mmHg]
Physical DescriptionWhite solid; [MSDSonline]
Stability/Shelf Life... PCB's are chemically very inert and are stable to conditions of hydrolysis and oxidation in industrial use.
Collision Cross Section · 3 items

168.5 Ų [M]+ [CCS Type: TIMS, Method: calibration with PAHs]

162.83 Ų [M]+ [CCS Type: TW; Buffer gas: N2; Ionization: GC-APCI+]

167.3 Ų [M-Cl+O]-

Other Experimental Properties · 2 items

... The accuracy of a method based on capillary gas chromatography for estimating vapor pressure of nonpolar compounds was tested by comparing vapor pressures measured by gas chromatography with literature values for the subcooled liquid. Two 1.0 m long fused silica columns were used, a poly(dimethylsiloxane) bonded phase column (BP-1) and a WCOT hydrocarbon phase column (Apolane-87). Gas chromatography measurements were carried out by using n(no)-C18 and n-C20 hydrocarbons as vapor pressure reference compounds. ... The gas chromatography method was applied to 30 polychlorinated biphenyl isomerids containing 1-7 chlorines. The average vapor pressure decreased by a factor of 4.5 for each chlorine added to the biphenyl core, although large differences in vapor pressure were measured for isomers of a particular chlorination level. ...

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 7.1% (3 of 42) of reports.

Warning

H373 (92.9%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]

P260, P273, P319, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 42 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 1 item

Hazard Traits - Bioaccumulation; Carcinogenicity; Dermatotoxicity; Developmental Toxicity; Endocrine Toxicity; Environmental Persistence; Environmental tox; Hematotoxicity; Hepatotoxicity and Digestive System Toxicity; Immunotoxicity; Reproductive Toxicity; Respiratory Toxicity

Fire PotentialFlame resistant.
Hazards SummaryEmergency medical treatment: see PCB-PBB; A skin and eye irritant; [HSDB] An eye irritant; May cause liver damage; [MSDSonline] See Chlorodiphenyl (42% chlorine). See Polychlorinated biphenyls and linked occupational disease.
Special Reports · 2 items

ALVARES AP ET AL; NATL RES COUNC CAN, (REP) NRCC/CNRC 18978, WORKSHOP COMB EFF XENOBIOTICS, 127-49 (1982). REVIEW ON ENZYME INDUCTIVE PROPERTIES OF PCBS. /POLYCHLORINATED BIPHENYLS/

TSCA CHIPs present a preliminary assessment of polychlorinated biphenyl's potential for injury to human health & the environment (available at EPA's TSCA Assistance Office: (202) 554-1404 or (800) 424-9065) /Polychlorinated biphenyls/

NIOSH Recommendations · 3 items

NIOSH considers chlorodiphenyl containing 54% chlorine to be a potential occupational carcinogen. /Aroclor 1254/

Chemistry & industry

Pharmacology

Biological Half-Life · 1 item

BIOLOGICAL HALF-LIFE OF 31 DICHLORO- TO DECHLOROBIPHENYL CONGENERS WERE MONITORED FOR 105 DAYS IN ADULT RAINBOW TROUT THAT WERE EXPOSED TO A SINGLE ORAL DOSE. IN WHOLE FISH, HALF-LIFE INCR FROM 5 DAYS TO NO APPARENT ELIMINATION AS THE NUMBER OF CHLORINES ON THE BIPHENYL INCR. THIS STRUCTURE-ACTIVITY RELATION WAS NOT AS EVIDENT IN MUSCLE WHERE HALF-LIFE RANGED FROM LESS THAN 5 DAYS TO 127 DAYS. DECLINE IN MUSCLE PCB MAY BE RELATED TO THE DECR IN LIPID LEVELS & REDISTRIBUTION OF CONGENERS WITHIN THE FISH. FROM STRUCTURE-ACTIVITY ANALYSIS OF HALF-LIFE IN WHOLE FISH, ELIMINATION IS ENHANCED FOR THOSE CONGENERS WITH LOWER CHLORINE CONTENT, WITH NO CHLORINE SUBSTITUTIONS IN THE ORTHO POSITIONS, & THOSE WITH 2 UNSUBSTITUTED CARBONS THAT ARE ADJACENT (VICINAL) ON THE BIPHENYL. A SIGNIFICANT DECLINE IN TOTAL PCB CONTENT IN WHOLE FISH, EQUIV TO HALF-LIFE OF 219 DAYS, WAS PARTLY DUE TO DECOMP OF THE PCB MIXTURE ADMIN, & SELECTIVE ELIMINATION OF LOWER CHLORINATED BIPHENYLS.

Metabolism/Metabolites · 2 items

A strain of Alcaligenes eutrophus, designated H850, that rapidly degrades a broad and unusual spectrum of polychlorinated biphenyls (PCBs) has been isolated and characterized. ... This strain was isolated from PCB-containing dredge spoils, grows well on biphenyl and 2-chlorobiphenyl but poorly on 3- and 4-chlorobiphenyl. Capillary gas-chromatographic analysis showed that biphenyl- grown resting cells of H850 degraded the components of 38 of the 41 largest peaks of Aroclor 1242 and 15 of the 44 largest peaks of Aroclor 1254, resulting in an overall reduction of PCBs by 81% for Aroclor 1242 (10 ppm) and 35% for Aroclor 1254 (10 ppm) in 2 days. H850 metabolized the predominantly ortho- substituted PCB congeners. ... The congener selectivity patterns indicate that a two-step process consisting of anaerobic dechlorination followed by oxidation by H850 can effectively degrade all of the congeners in Aroclor 1242 and possibly all those in Aroclor 1254.

PCBs are absorbed via inhalation, oral, and dermal routes of exposure. They are trasported in the blood, often bound to albumin. Due to their lipophilic nature they tend to accumulate in lipid-rich tissues, such as the liver, adipose, and skin. Metabolism of PCBs is very slow and varies based on the degree and position of chlorination. PCBs are metabolized by the microsomal monooxygenase system catalyzed by cytochrome P-450 enzymes to polar metabolites that can undergo conjugation with glutathione and glucuronic acid. The major metabolites are hydroxylated products which are excreted in the bile and faeces. The slow metabolism of PCBs means they tend to accumulate in body tissues. (L4, T6)

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Compound notes

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PubChem CID
40479
DTXSID
DTXSID7074165
ChEMBL
CHEMBL136151
ChEBI
CHEBI:81524
UNII
HD4MZI40CH
EC Number
690-199-6
Nikkaji
J126.399D

A generator column technique was used to directly determine log Kow (1-octanol/water partition coefficient) values for 15 polychlorinated biphenyl (PCB) cogeners and biphenyl. The method circumvented many experimental difficulties encountered with the traditional shake-flask system. Log Kow values generated by this procedure were compared with data obtained from the shake-flask method, 2 chromatographic estimation techniques and the computational method of Hansch and Leo. ...

Physicochemical properties

Melting point
115.76 °C · 115.76°C (estimate)
Boiling point
446.99 °C · 446.99°C (rough estimate)
Density
1.594 · 1.5940 (rough estimate)
refractive index
1.627 · 1.6270 (rough estimate)
storage temp.
Refrigerator, under inert atmosphere
solubility
Chloroform (Slightly), Dichloromethane (Slightly)
form
Solid
color
White to Off-White
Henry's Law Constant
7.8 · 7.8×10-2 mol/(m3Pa) at 25℃, Fang et al. (2006)
FDA UNII
4 MZI40CH · HD4MZI40CH
EPA Substance Registry System
2 · 2,3',4,4',5,5'-Hexachlorobiphenyl (52663-72-6)
Symbol(GHS)
8 · GHS08,GHS09
Signal word
Warning
Hazard statements
373 · H373-H410
Precautionary statements
273 · P273-P391-P501-P260-P314-P501
Hazardous Substances Data
52663 · 52663-72-6(Hazardous Substances Data)

NIOSH usually recommends that occupational exposures to carcinogens be limited to the lowest feasible concn. /Aroclor 1254/

Recommended Exposure Limit: 10 Hr Time-Weighted Avg: 0.001 mg/cu m. /Aroclor 1254/

Hazard Classes and CategoriesSTOT RE 2 (92.9%)
Shipment Methods and Regulations · 3 items

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.

Shipping Name/ Number DOT/UN/NA/IMO · 2 items

UN 2315; Polychlorinated biphenyls, liquid or solid

IMO 9.0; Polychlorinated biphenyls, liquid or solid

Skin, Eye, and Respiratory IrritationsIrritating to skin and eyes.
Hazardous Reactivities and IncompatibilitiesLiquid chlorine reacts exothermically with polychlorinated biphenyl heat transfer liquid.

Safety & protection

Storage ConditionsPCB material should be stored in closed containers, in ventilated areas ... /SRP: With appropriate air pollution control equipment./
Cleanup Methods · 2 items

... Dry sand or earth should be spread on the leak, or spill area. ...

Survey reports six case histories employing EPA's hazardous materials spills treatment trailer are reviewed. The trailer's ... treatment system has three mixed-media filters and three activated carbon columns to remove suspended, precipitated, and organic soluble materials. Spills of PCB, pentachlorophenol, kepone, termide (chlordane), heptachlor, aldrin, and dieldrin, toxaphene, and dinitrobutylphenol were treated by the EPA trailer, which was generally successful in mitigating environmental effects by filtering and carbon-adsorption. 90% removal was achieved for 21 of 23 compounds.

Disposal Methods · 4 items

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.

EXPERIMENTS ON THE COMBUSTION OF POLYCHLORINATED BIPHENYLS (PCB) IN 1 M-LONG TUBE FURNACE INDICATED THAT PCB CONTAINING APPROX 40% CL IS DESTROYED WITHIN 3-4 MIN AT 900-1000 °C USING 100% EXCESS AIR. TEMPERATURES GREATER THAN 1000 °C ARE REQUIRED TO DESTROY PCB CONTAINING APPROX 60% CL & DISTILLATION RESIDUES ARISING FROM PCB MFR. DOMESTIC WASTE INCINERATORS OPERATING AT 800-900 °C ARE UNLIKELY TO PROVE SUITABLE FOR INCINERATING WASTE CONTAINING TRACE AMT OF PCB. PYROLYSIS EXPERIMENTS AT 900 °C WITH NOMINAL RESIDENCE TIME OF 3.5 SEC GAVE 40-60% RECOVERY OF CL AS HCL FROM PCB.

POLYCHLORINATED BIPHENYLS CAN BE DESTROYED BY INCINERATION IF THE TRANSIT TIME IS LONG ENOUGH. DURING INCINERATION HEXACHLOROBENZENE IS FORMED; ITS RATE OF FORMATION INCR AT HIGH TEMP. IN ORDER FOR THE HEXACHLOROBENZENE TO BE DESTROYED, A TEMP OF 950 °C IS NEEDED. THIS RESULTS IN THE FORMATION OF A RESIDUE LESS THAN 100 MG OF HEXACHLOROBENZENE/KG. AT 800 °C & A TRANSIT TIME OF 2 SEC, A RESIDUE OF ABOUT 1200 MG/KG REMAINS.

Investigations were conducted of new and emerging technologies for the disposal of hazardous wastes, ... including molten salt combustion, fluidized bed incineration, high energy electron treatment of trace organic compounds in aqueous solution, the catalyzed wet oxidation of toxic chemicals, dehalogenation of compounds by treatment with ultraviolet (UV) light and hydrogen, UV/chlorinolysis of organics in aqueous solution, the catalytic hydrogenation-dechlorination of polychlorinated biphenyls (PCBs), and ultraviolet-ozone destruction. Theory, specific wastes treated, and economics are discussed. The major technologies investigated in detail were molten salt combustion, fluidized bed incineration, and ultraviolet/ozone destruction. Among wastes treated by emerging technologies are PCBs, various dioxins, pesticides and herbicides, chemical warfare agents, explosives and propellants, nitrobenzene, and hydrazine plus its derivatives.

Preventive Measures · 2 items

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.

Employees should wash their hands before eating, drinking and smoking ... and refrain from such activities in the polluted rooms. ...

Minimum Risk LevelIntermediate Oral: 0.03 ug/kg/day (L134)
Personal Protective Equipment (PPE) · 1 item

... Workers should be provided with suitable protective clothing: long-sleeved overalls, boots, overshoes, and bib-type aprons that cover the boot tops, and gloves. ... Safety glasses with side shields ... for eye protection. Respirators should be used in areas with PCB vapors and during installation and repair of containers and emergency activities. ...

Immediately Dangerous to Life or Health (IDLH)NIOSH considers chlorodiphenyl containing 54% chlorine to be a potential occupational carcinogen. /Aroclor 1254/

Toxicology

Treatment · 1 item

There are no specific treatments for PCB poisoning, since it is not usually recognized until after substantial chronic exposure. Only preventing further exposure and treating the observed symptoms can be done. Acute inhalation can be treated by administering oxygen. (L4)

Health Effects · 1 item

The most common health effects of PCBs are skin conditions such as chloracne and rashes. Chronic PCB exposure has also been shown to cause liver, stomach and kidney, damage, jaundice, edema, anemia, changes in the immune system, behavioral alterations, and impaired reproduction. (L4)

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Exposure RoutesOral (L4) ; inhalation (L4) ; dermal (L4)
Toxicity Summary · 1 item

The mechanism of action varies with the specific PCB. Dioxin-like PCBs bind to the aryl hydrocarbon receptor, which disrupts cell function by altering the transcription of genes, mainly be inducing the expression of hepatic Phase I and Phase II enzymes, especially of the cytochrome P450 family. Most of the toxic effects of PCBs are believed to be results of Ah receptor binding. Other PBCs are believed to interfere with calcium channels and/or change brain dopamine levels. PCBs can also cause endocrine disurption by altering the production of thyroid hormones and binding to estrogen receptors, which can stimulate the growth of certain cancer cells and produce other estrogenic effects, such as reproductive dysfunction. They will bioaccumulate by binding to receptor proteins such as uteroglobin. (A3, A4, A30, A66)

Signs and SymptomsChronic PCB exposure results in symptoms such as abdominal pain, nausea, vomiting, diarrhea, headache, dizziness, depression, nervousness, dermal and ocular lesions, fatigue, irregular menstrual cycles and a lowered immune response. (A3)
Medical SurveillanceMedical records should be kept for the entire length of employment of each worker and for the following 30 yr.
Human Toxicity Excerpts · 2 items

Nursing /by women exposed to PCB's/ ... should be discouraged because of the high amount of PCB's excreted with milk. ...

Food and Environmental Agents: Reported Sign or Symptom in Infant or Effect on Lactation: Polychlorinated biphenyls and polybrominated biphenyls: Lack of endurance, hypotonia, sullen, expressionless facies. /From Table 7/

Artificial Pollution Sources · 1 item

/SRP 1988: THIS PCB, BEING FOUND IN CLOPHEN A30, A40, A50, AND A60 BUT NOT IN AROCLORS/ ... FROM MANUFACTURING PLANTS, DURING DESTRUCTION OF MANUFACTURED ARTICLES CONTAINING PCBS IN MUNICIPAL & INDUSTRIAL WASTE-DISPOSAL BURNERS, THROUGH GRADUAL WEAR & WEATHERING OF PCB-CONTAINING PRODUCTS, & THROUGH LEACHING FROM LAND-FILL DUMPS.

Carcinogen Classification1, carcinogenic to humans. (L135)
Non-Human Toxicity Excerpts · 1 item

ISOMERICALLY PURE PCBS WERE TESTED AS INDUCERS OF HEPATIC DRUG-METABOLIZING ENZYMES IN THE RAT. THE CHLORINATED BIPHENYL ISOMERS CAN BE CATEGORIZED INTO 2 DISTINCT GROUPS OF INDUCERS, WHILE COMMERCIAL PCB MIXT HAVE CHARACTERISTICS OF BOTH GROUPS. BIPHENYLS CHLORINATED SYMMETRICALLY IN BOTH THE META AND PARA POSITIONS INCREASE THE FORMATION OF CYTOCHROME P448, BUT DECREASE THE AMINOPYRINE N-DEMETHYLASE ACTIVITY. BIPHENYL ISOMERS CHLORINATED IN BOTH THE PARA AND ORTHO POSITIONS INDUCE THE FORMATION OF CYTOCHROME P450 AND N-DEMETHYLASE ACTIVITY. ISOMERS WHICH ARE CHLORINATED IN ONLY 1 RING, OR ARE CHLORINATED IN BOTH RINGS BUT NOT IN THE PARA POSITIONS, HAVE VERY LITTLE ACTIVITY AS INDUCERS OF LIVER ENZYMES.

Toxicity DataLD50: 1010 mg/kg (Oral, Rat) (T14) LD50: 880 mg/kg (Intraperitoneal, Mouse) (T14)

Safety data

Signal word
Warning
Symbol(GHS)
GHS08,GHS09
Hazard statements
H373-H410
Precautionary statements
P273-P391-P501-P260-P314-P501
Hazardous Substances Data
52663-72-6(Hazardous Substances Data)
Absorption, Distribution and Excretion · 1 item

DISPOSITION OF 37 PCB CONGENERS & ADIPOSE TISSUE-PLASMA PARTITION OF 28 PCB CONGENERS WERE STUDIED IN 26 PERSONS OCCUPATIONALLY EXPOSED TO VARIOUS PCBS (20-54% CL). CONCN OF PCBS IN ADIPOSE TISSUE & PLASMA WERE RELATED TO DURATION & INTENSITY OF EXPOSURE. PCB CONCN IN ADIPOSE TISSUE WAS PROPORTIONAL TO THAT IN PLASMA, WITH A PARTITION FOR TOTAL PCBS OF APPROX 190:1 INDICATED FROM REGRESSION ANALYSIS. PCB CONGENERS WITH CL IN BOTH 4-POSITIONS OF BIPHENYL RING WERE MAJOR COMPONENTS IN PLASMA & ADIPOSE TISSUE. CONGENERS WITH UNSUBSTITUTED 3,4-POSITIONS ON 1 OR BOTH OF BIPHENYL RINGS WERE OBSERVED AT LOWER CONCENTRATIONS. IN CONTRAST, THOSE COMPOUNDS WITH SUBSTITUENTS AT 2,4- & 3,4-POSITIONS ON BOTH RINGS WERE PRESENT IN MUCH HIGHER PROPORTIONS IN BLOOD OR ADIPOSE TISSUE THAN IN PCB MIXTURES USED. THESE COMPONENTS ALSO HAD HIGHER ADIPOSE TISSUE-PLASMA PARTITION THAN THOSE WITH UNSUBSTITUTED 3,4-POSITIONS, REGARDLESS OF DEGREE OF CHLORINATION.

Uses & manufacturing

Uses · 2 items

Commercial production of PCBs stopped in 1977 in the US; [HSDB]

PCBs were used as coolants and lubricants in transformers, capacitors, and other electrical devices (such as fluorescent lights and refridgerators) produced before 1977. PCBs may contaminate the air and water near hazardous waste sites. In addition, PCBs bioaccumulate in the environment and may be found in fish, meat, and dairy products. (L4)

U.S. Exports(1986) No Data
U.S. Imports(1986) No Data
Methods of Manufacturing · 1 item

2,4,5-TRICHLOROANILINE IS COUPLED WITH 1,2,3-TRICHLOROBENZENE BY USING AN EXCESS OF THE LATTER REACTANT WHICH ALSO SERVES AS THE SOLVENT MEDIUM. THE COUPLING REACTION PROCEEDS SMOOTHLY AFTER THE ADDITION OF ISOAMYL NITRITE, AND THE PCB PRODUCT IS READILY ISOLATED AFTER A SERIES OF CHROMATOGRAPHIC PROCEDURES

Formulations/PreparationsDetected at trace levels in Clophen A50 and A60.
General Manufacturing InformationDOMESTIC /USA/ PRODUCTION OF POLYCHLORINATED BIPHENYLS WAS STOPPED IN OCTOBER 1977 /POLYCHLORINATED BIPHENYLS/

Applications

Uses2,3'',4,4'',5,5''-Hexachlorobiphenyl is a polychlorinated biphenyl (PCB) congeners.

Additional notes

DefinitionChEBI: 2,3',4,4',5,5'-Hexachlorobiphenyl is a trichlorobenzene and a hexachlorobiphenyl.