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1,3,6,8-Tetrachlorodibenzo-p-dioxin

HCID 36474
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
33423-92-6
Standard SMILES
Clc1cc(Cl)c2c(c1)Oc1c(Cl)cc(Cl)cc1O2
InChIKey
OTQFXRBLGNEOGH-UHFFFAOYSA-N
Molecular formula
C12H4Cl4O2
Average molar mass
322 g/mol
Monoisotopic mass
319.89654

Overview

1,3,6,8-tetrachlorodibenzodioxine is a polychlorinated dibenzodioxine.

Names & identifiers

Preferred name
1,3,6,8-Tetrachlorodibenzo-p-dioxin
IUPAC
1,3,6,8-tetrachlorodibenzo-p-dioxin
English name
1,3,6,8-TETRACHLORODIBENZO-P-DIOXIN
Molecular formula
C12H4Cl4O2
Molecular weight
321.97

Names & synonyms

1,3,6,8-TETRACHLORODIBENZO-P-DIOXIN33423-92-61,3,6,8-Tetrachlorodibenzodioxin1,3,6,8-TCDD1,3,6,8-Tetrachlorooxanthrene1,3,6,8-Tetrachlorodibenzo-para-dioxin1,3,6,8-tetrachlorodibenzodioxineDibenzo(b,e)(1,4)dioxin, 1,3,6,8-tetrachloro-P30XU4W6C1CHEBI:279361,3,6,8-tetrachlorodibenzo[b,e][1,4]dioxinDTXSID90872011
Show more names
1,3,6,8-TeCDD1,3,6,8-Tetrachlorobenzo-p-dioxin1,3,6,8-tetrachloro-dibenzo-p-dioxi1,3,6,8-Tetrachlorodibenzo[1,4]dioxin
Dibenzo[b,e][1,4]dioxin, 1,3,6,8-tetrachloro-1,3,6,8-tetrachlorodibenzo(b,e)(1,4)dioxinRefChem:72368DTXCID80819617809-099-2Dibenzo-p-dioxin, 1,3,6,8-tetrachloro-1,3,6,8-Tetrachlorobenzo-p-dioxin (~90%)BRN 1388027

Database identifiers

CAS
33423-92-6
PubChem CID
36474
DTXSID
DTXSID90872011
ChEBI
CHEBI:27936
UNII

Properties

Computed structural properties

XLogP
6.3
Topological polar surface area
18.5 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
18
Formal charge
0
Complexity
286

Experimental & physicochemical properties

SpringerMaterials PropertiesBoiling point
LogP6.29

Physicochemical properties

Melting point
219 °C · 219°C
Boiling point
407.62 °C · 407.62°C (rough estimate)
Density
1.643 · 1.6430 (estimate)
refractive index
1.643 · 1.6430 (estimate)
solubility
Chloroform (Heated, Very Slightly)
form
Solid
color
Beige
Water Solubility
0.32 ug/L · 0.32ug/L(20 ºC)
Henry's Law Constant
1.4 · 1.4×10-1 mol/(m3Pa) at 25℃, Webster et al. (1985)
EWG's Food Scores
1 · 1
FDA UNII
30 XU4W6C1 · P30XU4W6C1

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

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P264, P270, P273, P301+P316, P321, P330, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 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 CategoriesAcute Tox. 3 (100%)

Safety & protection

Minimum Risk LevelAcute Oral: 0.0002 ug/kg/day (L134) Intermediate Oral: 0.00002 ug/kg/day (L134) Chronic Oral: 0.000001 ug/kg/day (L134)

Toxicology

TreatmentTreatment of CDD exposure may include washing the area of contact, GI decontamination, administering an IV, or forced alkaline diuresis. (L346)
Health Effects · 1 item

Exposure to large amounts of CDDs causes chloracne, a severe skin disease with acne-like lesions that occur mainly on the face and upper body. CDDs may also cause liver damage and induce long-term alterations in glucose metabolism and subtle changes in hormonal levels. In addition, studies have shown that CDDs may disrupt the endocrine system and weaken the immune system, as well as cause reproductive damage and birth defects, central and peripheral nervous system pathology, thyroid disorders, endometriosis, and diabetes. (L177, L178)

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

CDDs are absorbed through oral, inhalation, and dermal routes of exposure. CDDs are carried in the plasma by serum lipids and lipoproteins, distributing mainly to the liver and adipose tissue. CDDs are very slowly metabolized by the microsomal monooxygenase system to polar metabolites that can undergo conjugation with glucuronic acid and glutathione. They may increase the rate of their own metabolism by inducing both phase I and phase II enzymes. The major routes of excretion of CDDs are the bile and the faeces, though smaller amounts are excreted in the urine and via lactation. (L177)

Uses & manufacturing

Uses · 1 item

Dioxins occur as by-products from the manufacture of organochlorides, the bleaching of paper, chlorination by waste and drinking water treatment plants, municipal solid waste and industrial incinerators, and natural sources such as volcanoes and forest fires. (L177, L178)

Applications

Uses1,3,6,8-Tetrachlorobenzo-p-dioxin is an intermediate in the synthesis of 1,2,3,6,7,8-Hexachlorodibenzodioxin which is a toxic polychlorinated dibenzo-p-dioxin detected in domestic meat and poultry.

Additional notes

DefinitionChEBI: 1,3,6,8-tetrachlorodibenzodioxine is a polychlorinated dibenzodioxine.

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Related reactions

1 records
New reaction record
HRID 439747 reaction equation
HRID 439747As productuspto-grants-1996_05

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
P30XU4W6C1
EC Number
809-099-2
Nikkaji
J74.779C
EPA Substance Registry System
1 · 1,3,6,8-Tetrachlorodibenzo-p-dioxin (33423-92-6)
Symbol(GHS)
9 · GHS09,GHS06
Signal word
Danger
Hazard statements
301 · H301-H410
Precautionary statements
264 · P264-P270-P301+P310-P321-P330-P405-P501-P273-P391-P501
RIDADR
2811 · 2811
HazardClass
6.1 · 6.1(a)
PackingGroup
I
Exposure Routes
Oral (L177) ; inhalation(L177) ; dermal (L177)
Toxicity Summary · 1 item

CDDs cause their toxic effects by binding to the aryl hydrocarbon receptor and subsequently altering the trascription of certain genes. The affinity for the Ah receptor depends on the structure of the specific CDD. The change in gene expression may result from the direct interaction of the Ah receptor and its heterodimer-forming partner, the aryl hydrocarbon receptor nuclear translocator, with gene regulatory elements or the initiation of a phosphorylation/dephosphorylation cascade that subsequently activates other transcription factors. The affected genes include several oncogenes, growth factors, receptors, hormones, and drug-metabolizing enzymes. The change in transcription/translation of these genes is believed to be the cause of most of the toxic effects of CDDs. (L177)

Signs and SymptomsIn addition to chloracne, CDD exposure causes skin rashes, discoloration, and excessive body hair. (L177)
Carcinogen Classification3, not classifiable as to its carcinogenicity to humans. (L135)

Safety data

ridadr
2811
Signal word
Danger
Symbol(GHS)
GHS09,GHS06
hazard_class
6.1(a)
packing_group
I
Hazard statements
H301-H410
Precautionary statements
P264-P270-P301+P310-P321-P330-P405-P501-P273-P391-P501