Basic information
- CAS
55684-94-1- Standard SMILES
Clc1cc2oc3c(Cl)c(Cl)c(Cl)c(Cl)c3c2cc1Cl- InChIKey
LVYBAQIVPKCOEE-UHFFFAOYSA-N- Molecular formula
- C12H2Cl6O
- Average molar mass
- 374.9 g/mol
- Monoisotopic mass
- 371.823681
Overview
1,2,3,4,7,8-Hexachlorodibenzofuran is a polychlorinated dibenzofuran.
Names & identifiers
- Preferred name
- 1,2,3,4,7,8-Hexachlorodibenzofuran
- IUPAC
- 1,2,3,4,7,8-hexachlorodibenzofuran
- English name
- 1,2,3,4,7,8-hexachlorodibenzofuran
- Molecular formula
- C12H2Cl6O
- Molecular weight
- 374.86
Names & synonyms
1,2,3,4,7,8-HEXACHLORODIBENZOFURAN70648-26-9HCDFDibenzofuran, 1,2,3,4,7,8-hexachloro-1,2,3,4,7,8-HxCDFBP4Q20NZGYDTXSID6029915Hexachlorobenzofuran, 1,2,3,4,7,8-PCDF 118RefChem:71277DTXCID0099153,4,5,6,11,12-hexachloro-8-oxatricyclo(7.4.0.02,7)trideca-1(13),2,4,6,9,11-hexaene
Show more names
1,2,3,4,7,8-HCDF1,2,3,4,7,8-HEXACDF123478HEXACHLORODIBENZO-PARA-FURANHexachlorodibenzofuran, 1,2,3,4,7,8-1,2,3,4,7,8-HEXACHLORODIPHENYLENEOXIDE1,2,3,4,7,8-Hexachlorodibenzofuran (>90%)1,2,3,4,7,8-Hexachlorodibenzofuran 50 μg/mL in Nonane
694-812-855684-94-1CHEMBL3427171,2,3,4,7,8-Hexachlorodibenzo[b,d]furan1,2,3,4,7,8-Hexachlorodibenzofuran(>90%)UNII-BP4Q20NZGYLVYBAQIVPKCOEE-UHFFFAOYSA-Norb2814123
Database identifiers
- CAS
55684-94-1、70648-26-9- PubChem CID
- 51130
- DTXSID
DTXSID6029915- ChEMBL
CHEMBL342717- ChEBI
CHEBI:81509- UNII
- BP4Q20NZGY
- EC Number
- 694-812-8
- Nikkaji
- J364.338G
Properties
Computed structural properties
- XLogP
- 6.9
- Topological polar surface area
- 13.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 355
Experimental & physicochemical properties
PolymersOther Classes -> Halogenated Polyaromatics
SpringerMaterials PropertiesBoiling point
LogP6.6
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section165.3 Ų [M]+ [CCS Type: TIMS, Method: calibration with PAHs]
Physicochemical properties
- Melting point
- 226 °C · 226°C
- Boiling point
- 510.41 °C · 510.41°C (rough estimate)
- Density
- 1.72 · 1.7200 (estimate)
- refractive index
- 1.718 · 1.7180 (rough estimate)
- solubility
- Chloroform (Very Slightly, Heated), Ethanol (Slightly)
- form
- Solid
- color
- White to Pale Yellow
- Water Solubility
- 0.008247 ug/L · 0.008247ug/L(22.5 ºC)
- Henry's Law Constant
- 6.9 · 6.9×10-1 mol/(m3Pa) at 25℃, Mackay et al. (2006)
- FDA UNII
- 4 Q20NZGY · BP4Q20NZGY
- EPA Substance Registry System
- 1 · 1,2,3,4,7,8-Hexachlorodibenzofuran (70648-26-9)
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 319 · H319-H413-H301
- Precautionary statements
- 264 · P264-P270-P301+P310-P321-P330-P405-P501-P264-P280-P305+P351+P338-P337+P313P
- RIDADR
- 2811 · 2811
- HazardClass
- 6.1 · 6.1(a)
- PackingGroup
- I
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
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P264+P265, P270, P273, P280, P301+P316, P305+P351+P338, P321, P330, P337+P317, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Hazard Traits - Bioaccumulation; Carcinogenicity; Dermatotoxicity; Developmental Toxicity; Endocrine Toxicity; Environmental Persistence; Environmental tox; Hematotoxicity; Hepatotoxicity and Digestive System Toxicity; Reproductive Toxicity
Regulation (EC) No 178/2002 (amended)
Hazards Summary
Teratogenicity observed in mice at doses not maternally toxic; [Shepard's Catalog of Teratogenic Agents] Causes other liver changes in acute intraperitoneal studies of mice and rats; Causes changes in liver weight, other liver changes, and effects on hepatic microsomal mixed oxidase in 4-day intermittent oral studies of mice; [RTECS] See CHLORINATED DIBENZOFURANS.
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Safety & protection
Protective Action Criteria (PAC)
0.0013 [mg/m3]
0.014 [mg/m3]
0.085 [mg/m3]
Toxicology
Health Effects
CDFs cause vomiting and diarrhea, anemia, more frequent lung infections, numbness and other effects on the nervous system, and mild changes in the liver. However, there were no permanent liver changes or definite liver damage found in people who ingested CDFs. (L952)
Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Exposure RoutesInhalation (L952) ; dermal (L952) ; oral (L952)
Toxicity Summary
Halogenated dibenzofurans (PCDFs and PBDFs) bind the aryl hydrocarbon receptor (AhR), which increases its ability to activate transcription in the XRE (xenobiotic resoponse element) promoter region. Specifically AhR binds to the PCDF, translocates it to the nucleus and together with hydrocarbon nuclear translocator (ARNT) and xenobiotic responsive element (XRE) increases the expression of CYP1A1 and aryl hydrocarbon hydroxylase (CYP1B1). AhR signaling also increseases conversion of arachidonic acid to prostanoids via cyclooxygenase-2, alters Wnt/beta-catenin signaling downregulating Sox9 and alters signaling by receptors for inflammatory cytokines. AhR signalling also alters proteasomal degradation of steroid hormone receptors, alters cellular UVB stress response and changes the differentiation of certain T-cell subsets. The resulting AhR mediated activation and alteration leads to body weight loss, cancer and thymic atrophy (characteristic of immune and endocrine disruption) which are common toxic responses to PCDFs and related toxic halogenated aryl hydrocarbons.
Signs and SymptomsSkin and eye irritations, especially severe acne, darkened skin color, and swollen eyelids with discharge are the most obvious health effects of the CDF poisoning. (L952)
Carcinogen Classification3, not classifiable as to its carcinogenicity to humans. (L135)
RAIS Toxicity Values
3.8
WHO/TEF
4e-07
WHO/TEF
7e-09
WHO/TEF
Safety data
- ridadr
- 2811
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_class
- 6.1(a)
- packing_group
- I
- Hazard statements
- H319-H413-H301
- Precautionary statements
- P264-P270-P301+P310-P321-P330-P405-P501-P264-P280-P305+P351+P338-P337+P313P
Chemistry & industry
Pharmacology
Metabolism/Metabolites
No information on the metabolism of dibenzofuran in mammalian organisms was found in the available literature. The bacteria Sphingomonas, Brevibacterium, Terrabacter, and Staphylococcus auricularis degrade dibenzofuran to 2,2',3-trihydroxybiphenyl via dibenzofuran 4,4a-dioxygenase. (L952)
Uses & manufacturing
UsesCDFs are created from production of coal tar and during incineration. They are used as insecticides, in the production of PVC, and in industrial bleaching. (L952)
Applications
Uses1,2,3,4,7,8-hexachlorodibenzofuran, is a toxic polychlorinated dibenzofurans (PCDD/F), detected in domestic meat and poultry. It can be used as purified standards for analytical, toxic, and biological studies of these environmental contaminants.
Additional notes
DefinitionChEBI: 1,2,3,4,7,8-Hexachlorodibenzofuran is a polychlorinated dibenzofuran.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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