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2,4,4',6-Tetrachlorobiphenyl

HCID 63107
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Basic information

CAS
32598-12-2
Standard SMILES
Clc1ccc(-c2c(Cl)cc(Cl)cc2Cl)cc1
InChIKey
RZFZBHKDGHISSH-UHFFFAOYSA-N
Molecular formula
C12H6Cl4
Average molar mass
292 g/mol
Monoisotopic mass
289.922361

Overview

2,4,4',6-tetrachlorobiphenyl is a tetrachlorobiphenyl that is 1,3,5-trichlorobenzene in which one of the hydrogens is replaced by a p-chlorophenyl group. It is a trichlorobenzene, a tetrachlorobiphenyl and a member of monochlorobenzenes.

Names & identifiers

Preferred name
2,4,4',6-Tetrachlorobiphenyl
IUPAC
1,3,5-trichloro-2-(4-chlorophenyl)benzene
English name
2,4,4',6-Tetrachlorobiphenyl
Molecular formula
C12H6Cl4
Molecular weight
291.99

Names & synonyms

2,4,4',6-tetrachlorobiphenyl2,4,4',6-Tetrachloro-1,1'-biphenyl1,1'-Biphenyl, 2,4,4',6-tetrachloro-2,4,6,4'-tetrachlorobiphenylUNII-S3VM605Y7SS3VM605Y7SDTXSID5074133CHEBI:342334,2',4',6'-TETRACHLOROBIPHENYL1,1'-BIPHENYL, 2,4,4',6-TETRACHLORORefChem:53577DTXCID6038538
Show more names
BZNO 75PCB NO 75Hexanal Impurity 22PCB No. 75 in Cyclohexane1,1'-BIPHENYL,2,4,4',6-TETRAC2.4.4'.6-Tetrachlorobiphenyl 10mg [32598-12-2]
32598-12-2PCB 75PCB No. 751,3,5-trichloro-2-(4-chlorophenyl)benzene2,4,4'6-TetrachlorobiphenylSCHEMBL2936537RZFZBHKDGHISSH-UHFFFAOYSA-NNS00005062

Database identifiers

CAS
32598-12-2
PubChem CID
63107
DTXSID
DTXSID5074133
ChEBI
CHEBI:34233
UNII
S3VM605Y7S
EC Number
690-150-9

Properties

Computed structural properties

XLogP
6.3
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
1
Heavy atoms
16
Formal charge
0
Complexity
213

Experimental & physicochemical properties

LogP6.03
Endocrine DisruptorsPotential endocrine disrupting compound

Physicochemical properties

Melting point
106.53 °C · 106.53°C (estimate)
Boiling point
374.95 °C · 374.95°C (rough estimate)
Density
1.442 · 1.4420 (rough estimate)
refractive index
1.612 · 1.6120 (rough estimate)
Water Solubility
91.1 ug/L · 91.1ug/L(25 ºC)
Henry's Law Constant
2.1 · 2.1×10-2 mol/(m3Pa) at 25℃, Paasivirta and Sinkkonen (2009)
FDA UNII
3 VM605Y7S · S3VM605Y7S
EPA Substance Registry System
2 · 2,4,4',6-Tetrachlorobiphenyl (32598-12-2)

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

Uses2,4,4'',6-Tetrachlorobiphenyl is a polychlorinated biphenyl (PCB) congeners.

Additional notes

DefinitionChEBI: A tetrachlorobiphenyl that is 1,3,5-trichlorobenzene in which one of the hydrogens is replaced by a p-chlorophenyl group.

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Nikkaji
J431.682G
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)