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4,4'-Dichlorobiphenyl

HCID 16308
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
2050-68-2
Standard SMILES
Clc1ccc(-c2ccc(Cl)cc2)cc1
InChIKey
YTBRNEUEFCNVHC-UHFFFAOYSA-N
Molecular formula
C12H8Cl2
Average molar mass
223.09 g/mol
Monoisotopic mass
222.0003056

Overview

4,4'-dichlorobiphenyl is a dichlorobiphenyl carrying chloro groups at positions 4 and 4' respectively. It is a dichlorobiphenyl and a member of monochlorobenzenes.

Names & identifiers

Preferred name
4,4'-Dichlorobiphenyl
IUPAC
1-chloro-4-(4-chlorophenyl)benzene
English name
4,4'-Dichlorobiphenyl
Molecular formula
C12H8Cl2
Molecular weight
223.1

Names & synonyms

4,4'-Dichlorobiphenyl2050-68-24,4'-DICHLORO-1,1'-BIPHENYLp,p-Dcbpp,p'-Dichlorobiphenyl1,1'-Biphenyl, 4,4'-dichloro-PCB 151-chloro-4-(4-chlorophenyl)benzeneBiphenyl, 4,4'-dichloro-4-DCB cpdDOF6S5DT2RDTXSID0022515
Show more names
pcb154,4'-CB4,4'-PCBBZ NO 15NSC 1141PCB NO 15p,p’-dcbpBALLSCHMITER NO 15
NSC-1141CHEBI:34364RefChem:53597DTXCID502515218-095-4PCB No. 15Biphenyl,4'-dichloro-4,4 inverted exclamation marka-Dichlorobiphenyl

Database identifiers

CAS
2050-68-2
PubChem CID
16308
DTXSID
DTXSID0022515
ChEMBL
CHEMBL14295
ChEBI
CHEBI:34364
UNII
DOF6S5DT2R
EC Number
218-095-4
Nikkaji
J7.868I

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
14
Formal charge
0
Complexity
145

Experimental & physicochemical properties

SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP5.23
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section141.8 Ų [M]+ [CCS Type: TIMS, Method: calibration with PAHs]

Physicochemical properties

Melting point
288 ℃ · 288℃
Boiling point
289.78 °C · 289.78°C (rough estimate)
Density
1.249 · 1.2490 (rough estimate)
refractive index
1.594 · 1.5940 (rough estimate)
Flash point
-12 ℃ · -12℃
storage temp.
2 · 2-8°C
Water Solubility
53 ug/L · 53ug/L(25 ºC)
Henry's Law Constant
7 · 7.0×10-2 mol/(m3Pa) at 25℃, Li et al. (2003)

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 · 5 items

This chemical does not meet GHS hazard criteria for 7.1% (3 of 42) of reports.

Warning

H373 (92.9%): 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 InformationSubstance: 4,4'-dichlorobiphenyl
Hazard Classes and CategoriesSTOT RE 2 (92.9%)

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 · 2 items

4,4'-Dichlorobiphenyl has known human metabolites that include 4,4-²-Dichloro-3-biphenylol.

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

Uses4,4''-Dichlorobiphenyl is a polychlorinated biphenyl (PCB) congeners.

Upstream & downstream products

Downstream products

2,4'-Dichlorobiphenyl

Additional notes

DefinitionChEBI: A dichlorobiphenyl carrying chloro groups at positions 4 and 4' respectively.

Suppliers

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Related reactions

4 records
New reaction record
HRID 268508 reaction equation
HRID 268508As productuspto-grants-1976_03
HRID 329313 reaction equation
HRID 329313As productuspto-grants-1977_04
HRID 1108513 reaction equation
HRID 1108513As productuspto-grants-2000_05
HRID 2119232 reaction equation
HRID 2119232As reactantuspto-grants-1987_07

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
InChI
InChI=1S/C12H8Cl2/c13-11-5-1-9(2-6-11)10-3-7-12(14)8-4-10/h1-8H
InChIKey
YTBRNEUEFCNVHC-UHFFFAOYSA-N
SMILES
C1(C2=CC=C(Cl)C=C2)=CC=C(Cl)C=C1
CAS DataBase Reference
2050 · 2050-68-2(CAS DataBase Reference)
FDA UNII
6 S5DT2R · DOF6S5DT2R
EPA Substance Registry System
4 · 4,4'-Dichlorobiphenyl (2050-68-2)
Symbol(GHS)
2 · GHS02,GHS07,GHS08,GHS09
Signal word
Danger
Hazard statements
225 · H225-H304-H315-H336-H373-H410
Precautionary statements
210 · P210-P261-P273-P301+P310-P331-P501
Hazard Codes
F,Xi,Xn,N
Risk Statements
11 · 11-36/37/38-22-50/53-33-67-65-38
Safety Statements
16 · 16-26-33-36-61-60-35-62
RIDADR
2315 · 2315
WGK Germany
3 · 3
RTECS
3912500 · DV3912500
HazardClass
9 · 9
PackingGroup
II
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

wgk
3
rtecs
DV3912500
ridadr
2315
risk_code
11-36/37/38-22-50/53-33-67-65-38
Signal word
Danger
Symbol(GHS)
GHS02,GHS07,GHS08,GHS09
hazard_code
F,Xi,Xn,N
safety_code
16-26-33-36-61-60-35-62
hazard_class
9
packing_group
II
Hazard statements
H225-H304-H315-H336-H373-H410
Precautionary statements
P210-P261-P273-P301+P310-P331-P501