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2,2',3,3',4,6-Hexachlorobiphenyl

HCID 91680
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
61798-70-7
Standard SMILES
Clc1cccc(-c2c(Cl)cc(Cl)c(Cl)c2Cl)c1Cl
InChIKey
WDLTVNWWEZJMPF-UHFFFAOYSA-N
Molecular formula
C12H4Cl6
Average molar mass
360.9 g/mol
Monoisotopic mass
357.844416

Overview

2,2',3,3',4,6-Hexachlorobiphenyl is one of 209 polychlorinated biphenyls (PCBs). PCBs are a group of synthetic organic compounds with 1-10 chlorine atoms attached to biphenyl. They were manufactured as commercial mixtures but banned in the 1970's because they were found to bioaccumulate and cause harmful health effects. However, PCBs do not break down readily and are still found in the environment. (L4)

Names & identifiers

Preferred name
2,2',3,3',4,6-Hexachlorobiphenyl
IUPAC
1,2,3,5-tetrachloro-4-(2,3-dichlorophenyl)benzene
English name
2,2',3,3',4,6-Hexachlorobiphenyl
Molecular formula
C12H4Cl6
Molecular weight
360.88

Names & synonyms

2,2',3,3',4,6-HEXACHLOROBIPHENYL61798-70-72,2',3,3',4,6-Hexachloro-1,1'-biphenylUNII-H530VIV1861,1'-Biphenyl, 2,2',3,3',4,6-Hexachloro-H530VIV186RefChem:53417PCB 1311,2,3,5-tetrachloro-4-(2,3-dichlorophenyl)benzenePCB No. 131SCHEMBL4450215DTXSID8074780
Show more names
BZNO 131PCB NO 131PCB No. 131 in Cyclohexane
WDLTVNWWEZJMPF-UHFFFAOYSA-NQ27279649

Database identifiers

CAS
61798-70-7
PubChem CID
91680
DTXSID
DTXSID8074780
UNII
H530VIV186
EC Number
690-280-6
Nikkaji
J151.540C

Properties

Computed structural properties

XLogP
6.8
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
1
Heavy atoms
18
Formal charge
0
Complexity
286

Experimental & physicochemical properties

LogP6.43

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)
Water Solubility
12.12 ug/L · 12.12ug/L(20 ºC)
Henry's Law Constant
1.5 · 1.5×10-1 mol/(m3Pa) at 25℃, Murphy et al. (1987)
FDA UNII
530 VIV186 · H530VIV186
EPA Substance Registry System
2 · 2,2',3,3',4,6-Hexachlorobiphenyl (61798-70-7)

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 · 3 items

This chemical does not meet GHS hazard criteria for 100% (3 of 3) of all reports.

Not Classified

Aggregated GHS information provided per 3 reports by companies from 1 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesNot Classified

Safety & protection

Minimum Risk LevelIntermediate Oral: 0.03 ug/kg/day (L134)

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)

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)

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

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)

Uses & manufacturing

Uses · 1 item

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)

Applications

Uses2,2'',3,3'',4,6-Hexachlorobiphenyl is a polychlorinated biphenyl (PCB) congeners.

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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)
Carcinogen Classification1, carcinogenic to humans. (L135)
Toxicity DataLD50: 1010 mg/kg (Oral, Rat) (T14) LD50: 880 mg/kg (Intraperitoneal, Mouse) (T14)