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2,2',3,3',4,5,5',6'-Octachlorobiphenyl

HCID 40482
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
52663-75-9
Standard SMILES
Clc1cc(-c2c(Cl)c(Cl)cc(Cl)c2Cl)c(Cl)c(Cl)c1Cl
InChIKey
HJBYDWKNARZTMJ-UHFFFAOYSA-N
Molecular formula
C12H2Cl8
Average molar mass
429.8 g/mol
Monoisotopic mass
425.766472

Overview

2,2',3,3',4,5,5',6'-Octachlorobiphenyl 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',4,5,5',6'-Octachlorobiphenyl
IUPAC
1,2,3,4-tetrachloro-5-(2,3,5,6-tetrachlorophenyl)benzene
English name
2,2',3,3',4',5,5',6-Octachlorobiphenyl
Molecular formula
C12H2Cl8
Molecular weight
429.77

Names & synonyms

2,2',3,3',4,5,5',6'-Octachlorobiphenyl2,2',3,3',4,5,5',6'-Octachloro-1,1'-biphenylUNII-95B469I42W1,1'-Biphenyl, 2,2',3,3',4,5,5',6'-octachloro-95B469I42W1,1'-Biphenyl, 2,2',3,3',4,5,5'6'-octachloro-DTXSID2074168RefChem:53439DTXCID304124752663-75-92,2',3,3',4',5,5',6-OCTACHLOROBIPHENYLPCB 199
Show more names
PCB NO 201PCB No. 199 10 μg/mL in Isooctane2,2',3,3',4,5,5',6'-OCTACB UNLABELED CERTIFIED STANDARD
1,2,3,4-tetrachloro-5-(2,3,5,6-tetrachlorophenyl)benzenePcb No. 201SCHEMBL44568051,1'-Biphenyl, 2,2',3,3',4',5,5',6-octachloroSCHEMBL30035000HJBYDWKNARZTMJ-UHFFFAOYSA-NPCB No. 199 10 |Ig/mL in IsooctanePCB No. 199 10 microg/mL in Isooctane

Database identifiers

CAS
52663-75-9
PubChem CID
40482
DTXSID
DTXSID2074168
UNII
95B469I42W
EC Number
690-195-4
Nikkaji
J126.428A

Properties

Computed structural properties

XLogP
8.2
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
1
Heavy atoms
20
Formal charge
0
Complexity
325

Experimental & physicochemical properties

LogP7.35
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section177.1 Ų [M]+ [CCS Type: TIMS, Method: calibration with PAHs]

Physicochemical properties

Melting point
150.67 °C · 150.67°C (estimate)
Boiling point
509.96 °C · 509.96°C (rough estimate)
Density
1.717 · 1.7170 (rough estimate)
refractive index
1.638 · 1.6380 (rough estimate)
Henry's Law Constant
9.9 · 9.9×10-1 mol/(m3Pa) at 25℃, Brunner et al. (1990)
FDA UNII
95 B469I42W · 95B469I42W
EPA Substance Registry System
2 · 2,2',3,3',4,5,5',6'-Octachlorobiphenyl (52663-75-9)

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)

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)

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'',4,5,5'',6''-Octachlorobiphenyl is a polychlorinated biphenyl (PCB) congeners.

Upstream & downstream products

Downstream products

2,4,4'-Trichlorobiphenyl

Suppliers4 total

天津阿尔塔科技有限公司022-65378550-8551 · [email protected]
Shaanxi Didu New Materials Co. Ltd+86-86-17392712779 +86-13289823923 · [email protected]
深圳聚合生化科技有限公司+86-400-002-6226 13028896684 · [email protected]
北京百灵威科技有限公司18210857532 18210857532 · [email protected]

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Compound notes

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