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2,2',5-Trichlorobiphenyl

HCID 37803
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
37680-65-2
Standard SMILES
Clc1ccc(Cl)c(-c2ccccc2Cl)c1
InChIKey
DCMURXAZTZQAFB-UHFFFAOYSA-N
Molecular formula
C12H7Cl3
Average molar mass
257.5 g/mol
Monoisotopic mass
255.961333

Overview

2,2',5-Trichlorobiphenyl 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',5-Trichlorobiphenyl
IUPAC
1,4-dichloro-2-(2-chlorophenyl)benzene
English name
2,2',5-Trichlorobiphenyl
Molecular formula
C12H7Cl3
Molecular weight
257.54

Names & synonyms

2,2',5-TRICHLOROBIPHENYL37680-65-2PCB 182,5,2'-Trichlorobiphenyl1,1'-Biphenyl, 2,2',5-trichloro-1,4-dichloro-2-(2-chlorophenyl)benzene2,2',5-Trichloro-1,1'-biphenyl2,2',5'-Trichlorobiphenyl6LEV53Y3OXDTXSID60734912,2',5-TBPRefChem:53543
Show more names
CB-18PCB-18BZ NO 182,5,2'-CB2,2′,5-PCBCB 18 (chlorocarbon)C20001800 PCB No. 182,5,2’-trichlorobiphenyl
DTXCID7039383621-394-6PCB No. 182,2',5-TrichlorobiphenyPCB No 18UNII-6LEV53Y3OXBRN 24533472,2',5-trichlorbiphenyl

Database identifiers

CAS
37680-65-2
PubChem CID
37803
DTXSID
DTXSID6073491
ChEMBL
CHEMBL13843
UNII
6LEV53Y3OX
EC Number

Properties

Computed structural properties

XLogP
5.6
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
1
Heavy atoms
15
Formal charge
0
Complexity
207

Experimental & physicochemical properties

SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP5.34
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section147.6 Ų [M]+ [CCS Type: TIMS, Method: calibration with PAHs]

Physicochemical properties

Melting point
44 ℃ · 44℃
Boiling point
334.36 °C · 334.36°C (rough estimate)
Density
1.351 · 1.3510 (rough estimate)
refractive index
1.604 · 1.6040 (rough estimate)
storage temp.
room temp
Water Solubility
0.64 mg/L · 0.64mg/L(25 ºC)
Henry's Law Constant
2.9 · 2.9×10-1 mol/(m3Pa) at 25℃, Bhangare et al. (2019)
FDA UNII

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 · 4 items

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 42 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationHazard Traits - Carcinogenicity; Dermatotoxicity; Endocrine Toxicity; Immunotoxicity; Reproductive Toxicity
Hazard Classes and CategoriesSTOT RE 2 (100%)

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)

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 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'',5-Trichlorobiphenyl is a polychlorinated biphenyl (PCB) congeners.

Upstream & downstream products

Downstream products

2,4,4'-Trichlorobiphenyl

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
621-394-6
Nikkaji
J150.408H
6 LEV53Y3OX · 6LEV53Y3OX
EPA Substance Registry System
2 · 2,2',5-Trichlorobiphenyl (37680-65-2)
Symbol(GHS)
8 · GHS08
Signal word
Warning
Hazard statements
373 · H373-H410
Precautionary statements
273 · P273-P391-P501-P260-P314-P501
Hazard Codes
N,Xn
Risk Statements
33 · 33-50/53
Safety Statements
35 · 35-60-61
RIDADR
3432 · UN 3432 9/PG 2
RTECS
8820000 · DV8820000
Toxicity
150 mg/kg/3D-I · TDLo ipr-rat: 150 mg/kg/3D-I TXAPA9 33,94,75
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)

Safety data

rtecs
DV8820000
ridadr
UN 3432 9/PG 2
Toxicity
TDLo ipr-rat: 150 mg/kg/3D-I TXAPA9 33,94,75
risk_code
33-50/53
Signal word
Warning
Symbol(GHS)
GHS08
hazard_code
N,Xn
safety_code
35-60-61
Hazard statements
H373-H410
Precautionary statements
P273-P391-P501-P260-P314-P501