2,2',3,3',4,5',6,6'-Octachlorobiphenyl
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Basic information
- CAS
40186-71-8- Standard SMILES
Clc1cc(Cl)c(-c2c(Cl)c(Cl)cc(Cl)c2Cl)c(Cl)c1Cl- InChIKey
LJQOBQLZTUSEJA-UHFFFAOYSA-N- Molecular formula
- C12H2Cl8
- Average molar mass
- 429.8 g/mol
- Monoisotopic mass
- 425.766472
Overview
2,2',3,3',4,5',6,6'-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',6,6'-Octachlorobiphenyl
- IUPAC
- 1,2,3,5-tetrachloro-4-(2,3,5,6-tetrachlorophenyl)benzene
- English name
- 2,2',3,3',4,5',6,6'-OCTACHLOROBIPHENYL
- Molecular formula
- C12H2Cl8
- Molecular weight
- 429.77
Names & synonyms
2,2',3,3',4,5',6,6'-Octachlorobiphenyl40186-71-8PCB 2012,2',3,3',4,5',6,6'-Octachloro-1,1'-biphenylUNII-N731BPT821N731BPT8211,1'-Biphenyl, 2,2',3,3',4,5',6,6'-octachloro-DTXSID4074148RefChem:53432DTXCID00397281,2,3,5-tetrachloro-4-(2,3,5,6-tetrachlorophenyl)benzene1,1'-Biphenyl,2,2',3,3',4,5',6,6'-octachloro-
Show more names
BZNO 200PCB NO 200C20020000 PCB No. 200PCB No. 201 10 μg/mL in IsooctaneL20020100IO PCB No. 201 10μg/mLin Isooctane
SCHEMBL4459306LJQOBQLZTUSEJA-UHFFFAOYSA-NPCB No. 201 10 |Ig/mL in IsooctanePCB No. 201 10 microg/mL in IsooctaneNS00077037Q272846431,1'-Biphenyl, 2,2',3,3',4',5,6,6'-octachloro2,2',3,3',4,5',6,6'-Octachloro-1,1'-biphenyl #
Database identifiers
- CAS
40186-71-8
Properties
Computed structural propertiesFilling in
- XLogP
- 7.7
- 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
LogP7.21
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section174.7 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
- 1 · 1.0×10-2 mol/(m3Pa) at 25℃, Bamford et al. (2000)
- FDA UNII
- 731 BPT821 · N731BPT821
- EPA Substance Registry System
- 2 · 2,2',3,3',4,5',6,6'-Octachlorobiphenyl (40186-71-8)
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
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
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
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
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
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
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'',4,5,6,6''-Octachlorobiphenyl is a polychlorinated biphenyl (PCB) congeners.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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