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3,5-Dichlorobiphenyl

HCID 36981
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Basic information

CAS
34883-41-5
Standard SMILES
Clc1cc(Cl)cc(-c2ccccc2)c1
InChIKey
QHZSDTDMQZPUKC-UHFFFAOYSA-N
Molecular formula
C12H8Cl2
Average molar mass
223.09 g/mol
Monoisotopic mass
222.0003056

Overview

3,5-dichlorobiphenyl is a dichlorobiphenyl that is 1,3-dichlorobenzene in which the hydrogen at position 5 has been replaced by a phenyl group. It is a dichlorobenzene and a dichlorobiphenyl.

Names & identifiers

Preferred name
3,5-Dichlorobiphenyl
IUPAC
1,3-dichloro-5-phenylbenzene
English name
3,5-Dichlorobiphenyl
Molecular formula
C12H8Cl2
Molecular weight
223.1

Names & synonyms

3,5-Dichlorobiphenyl34883-41-53,5-DICHLORO-1,1'-BIPHENYL1,3-dichloro-5-phenylbenzenePCB 14IXL47709VMDTXSID5074137CHEBI:34326RefChem:53621DTXCID5038919630-495-41,1'-Biphenyl, 3,5-dichloro-
Show more names
BZNO 143,5-PCBBALLSCHMITER NO 14C20001400 PCB No. 14PCB No. 14 in Cyclohexane
PCB No. 14MFCD00055256PCB No 14UNII-IXL47709VMQHZSDTDMQZPUKC-UHFFFAOYSA-N3,5-DicbSCHEMBL308200SCHEMBL534318

Database identifiers

CAS
34883-41-5
PubChem CID
36981
DTXSID
DTXSID5074137
ChEMBL
CHEMBL125602
ChEBI
CHEBI:34326
UNII
IXL47709VM
EC Number
630-495-4
Nikkaji
J147.960A

Properties

Computed structural properties

XLogP
4.8
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
1
Heavy atoms
14
Formal charge
0
Complexity
165

Experimental & physicochemical properties

SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP5.41
Endocrine DisruptorsPotential endocrine disrupting compound

Physicochemical properties

Melting point
62 ℃ · 62℃
Boiling point
289.78 °C · 289.78°C (rough estimate)
Density
1.249 · 1.2490 (rough estimate)
refractive index
1.6257 · 1.6257 (589.3 nm 25℃)
BRN
1944311 · 1944311
Henry's Law Constant
2.7 · 2.7×10-2 mol/(m3Pa) at 25℃, Paasivirta and Sinkkonen (2009)
FDA UNII
47709 VM · IXL47709VM
EPA Substance Registry System
3 · 3,5-Dichlorobiphenyl (34883-41-5)
Symbol(GHS)
8 · GHS08,GHS09
Signal word
Warning
Hazard statements
373 · H373-H410
Precautionary statements
273 · P273-P314
Hazard Codes
N,Xn
Risk Statements
33 · 33-50/53
Safety Statements
35 · 35-60-61
RIDADR
2315 · 2315
WGK Germany
3 · 3
HazardClass
9 · 9
PackingGroup
II

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 7.3% (3 of 41) of reports.

Warning

H373 (92.7%): 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 (92.7%)

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)

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
ridadr
2315
risk_code
33-50/53
Signal word
Warning
Symbol(GHS)
GHS08,GHS09
hazard_code
N,Xn
safety_code
35-60-61
hazard_class
9
packing_group
II
Hazard statements
H373-H410
Precautionary statements
P273-P314

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

Uses3,5-Dichlorobiphenyl is a polychlorinated biphenyl (PCB) congeners.

Additional notes

DefinitionChEBI: A dichlorobiphenyl that is 1,3-dichlorobenzene in which the hydrogen at position 5 has been replaced by a phenyl group.

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