2,2',3,5'-Tetrachlorobiphenyl
Basic information
- CAS
41464-39-5- Standard SMILES
Clc1ccc(Cl)c(-c2cccc(Cl)c2Cl)c1- InChIKey
ALDJIKXAHSDLLB-UHFFFAOYSA-N- Molecular formula
- C12H6Cl4
- Average molar mass
- 292 g/mol
- Monoisotopic mass
- 289.922361
Overview
2,2',3,5-Tetrachlorobiphenyl 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',3,5'-Tetrachlorobiphenyl
- IUPAC
- 1,2-dichloro-3-(2,5-dichlorophenyl)benzene
- English name
- 2,2',3,5'-Tetrachlorobiphenyl
- Molecular formula
- C12H6Cl4
- Molecular weight
- 291.99
Names & synonyms
2,2',3,5'-TETRACHLOROBIPHENYL41464-39-5PCB 442,2',3,5'-Tetrachloro-1,1'-biphenyl1,1'-Biphenyl, 2,2',3,5'-tetrachloro-UNII-486UPI8AXY486UPI8AXYDTXSID8038302RefChem:53468DTXCID6018302PCB No. 442,2 inverted exclamation marka,3,5 inverted exclamation marka-Tetrachlorobiphenyl
Show more names
CB-44PCB-445′-PCBBZ NO 44PCB NO 44，3，5&＃0392,2′,3,5′-PCBPCB 44(2，2&＃039PCB No 44 OEKANALC20004400 PCB No. 44
2,2',3,5'-TetracbSCHEMBL4450231SCHEMBL9784010SCHEMBL97840152,2'3,5'-Tetrachlorobiphenyl2,2',3,5'-TetrachlorbiphenylMSK3643PCB No 44, analytical standard
Database identifiers
- CAS
41464-39-5- PubChem CID
- 38875
- DTXSID
Properties
Computed structural properties
- XLogP
- 5.8
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 1
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 233
Experimental & physicochemical properties
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP5.81
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section154.7 Ų [M]+ [CCS Type: TIMS, Method: calibration with PAHs]
Physicochemical properties
- Melting point
- 45 ℃ · 45℃
- 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)
- storage temp.
- 20 °C · −20°C
- Water Solubility
- 80 ug/L · 80ug/L(25 ºC)
- Henry's Law Constant
- 5.4 · 5.4×10-3 mol/(m3Pa) at 25℃, Bhangare et al. (2019)
- FDA UNII
- 486 UPI8AXY · 486UPI8AXY
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
Warning
H373 (100%): 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 41 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationHazard Traits - Carcinogenicity; Dermatotoxicity; Developmental Toxicity; Endocrine Toxicity; Hepatotoxicity and Digestive System Toxicity; Immunotoxicity; Neurotoxicity; Reproductive Toxicity
Hazard Classes and CategoriesSTOT RE 2 (100%)
Safety & protection
Minimum Risk Level
Intermediate Oral: 0.03 ug/kg/day (L134)
Intermediate 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)
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)
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)
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)
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)
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