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2,2',4-Trichlorobiphenyl

HCID 37804
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
37680-66-3
Standard SMILES
Clc1ccc(-c2ccccc2Cl)c(Cl)c1
InChIKey
YKKYCYQDUUXNLN-UHFFFAOYSA-N
Molecular formula
C12H7Cl3
Average molar mass
257.5 g/mol
Monoisotopic mass
255.961333

Overview

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

Names & synonyms

2,2',4-TRICHLOROBIPHENYL37680-66-31,1'-Biphenyl, 2,2',4-trichloro-PCB 172,2',4-Trichloro-1,1'-biphenylUNII-YA6CZ8O8B4YA6CZ8O8B4DTXSID1073492RefChem:53538DTXCID20393841,1'-Biphenyl,2,2',4-trichloro-2,4-dichloro-1-(2-chlorophenyl)benzene
Show more names
PCB-172,4,2'-CBPCB NO 172,2′,4-PCBPCB15 in Octane2,4,2'-Trichlorobiphenyl2,2',4-TRICB CERTIFIED STANDARD
Pcb No. 17SCHEMBL432622SCHEMBL435069SCHEMBL435070SCHEMBL1984033SCHEMBL2934558CHEMBL1797260SCHEMBL14975559

Database identifiers

CAS
37680-66-3
PubChem CID
37804
DTXSID
DTXSID1073492
ChEMBL
CHEMBL1797260
UNII
YA6CZ8O8B4
EC Number
634-863-5

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
15
Formal charge
0
Complexity
207

Experimental & physicochemical properties

LogP5.39
Endocrine DisruptorsPotential endocrine disrupting compound

Physicochemical properties

Melting point
63.91 °C · 63.91°C (estimate)
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)
Water Solubility
259.2 ug/L · 259.2ug/L(20 ºC)
Henry's Law Constant
3.3 · 3.3×10-2 mol/(m3Pa) at 25℃, Bamford et al. (2002)
FDA UNII
6 CZ8O8B4 · YA6CZ8O8B4
EPA Substance Registry System
2 · 2,2',4-Trichlorobiphenyl (37680-66-3)
Symbol(GHS)
8 · GHS08,GHS09
Signal word
Warning

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 41 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

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)

Exposure RoutesOral (L4) ; inhalation (L4) ; dermal (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 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'',4-Trichlorobiphenyl is a polychlorinated biphenyl (PCB) congeners.

Suppliers23 total

阿诺西(上海)生物技术有限公司400-1107768 15058188853 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
杭州研富贸易有限公司

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Nikkaji
J437.632C
Hazard statements
410 · H410-H373
Precautionary statements
273 · P273-P391-P501-P260-P314-P501
Hazard Codes
N
Risk Statements
33 · 33-50/53
Safety Statements
35 · 35-60-61
RIDADR
2315 · UN 2315 9/PG 2
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

ridadr
UN 2315 9/PG 2
risk_code
33-50/53
Signal word
Warning
Symbol(GHS)
GHS08,GHS09
hazard_code
N
safety_code
35-60-61
Hazard statements
H410-H373
Precautionary statements
P273-P391-P501-P260-P314-P501
15990061515 · [email protected]
上海稳同科技有限公司02151600108 13062666369 · [email protected]
上海毕楷科技有限公司18516304666 · [email protected]
山东西亚化学有限公司13355009207 13355009207 · [email protected]
上海倍卓生物科技有限公司021-61119791,13386096464 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
天津阿尔塔科技有限公司022-65378550-8551 · [email protected]
九鼎化学(上海)科技有限公司4009209199 · [email protected]
上海西陇生化科技有限公司021-52907766-8042
上海源叶生物科技有限公司18916372613 · [email protected]
成都华纯科技有限公司400-1166-196 15982826727 · [email protected]
Shaanxi Didu New Materials Co. Ltd+86-86-17392712779 +86-13289823923 · [email protected]
上海臻励生物科技有限公司021-16621358918; 18516310516;16621358918;13045646768 · [email protected]
深圳聚合生化科技有限公司+86-400-002-6226 13028896684 · [email protected]
Aladdin Scientific[email protected]
上海博湖生物科技有限公司021-57763112 13585886131 · [email protected]
青岛腾龙微波科技有限公司0532-83818797 17669478191 · [email protected]
北京百灵威科技有限公司18210857532 18210857532 · [email protected]
DAYANG CHEM (HANGZHOU) CO.,LTD+86-88938639 +86-17705817739 · [email protected]
上海博拓生物科技有限公司16621358918 · [email protected]