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Dibenzo-P-dioxin

HCID 9216
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
262-12-4
Standard SMILES
c1ccc2c(c1)Oc1ccccc1O2
InChIKey
NFBOHOGPQUYFRF-UHFFFAOYSA-N
Molecular formula
C12H8O2
Average molar mass
184.19 g/mol
Monoisotopic mass
184.05242949

Overview

Dibenzo-p-dioxin appears as white crystals or crystalline solid. (NTP, 1992)

Names & identifiers

Preferred name
Dibenzo-P-dioxin
IUPAC
dibenzo-p-dioxin
English name
Dibenzo-p-dioxin
Molecular formula
C12H8O2
Molecular weight
184.19

Names & synonyms

DIBENZO-P-DIOXINOxanthrene262-12-4Dibenzo[b,e][1,4]dioxinDibenzodioxinPhenodioxinDiphenylene dioxideDibenzo[1,4]dioxinDibenzo(1,4)dioxinDibenzo(b,e)(1,4)dioxinNCI-C03656DTXSID8020410
Show more names
ai308911DIBENZODIOXINEDIBENZO-P-DIOXANEDibenzo-p-dioxine
O1B5KJ235IAI3 08911DTXCID60410CHEBI:28891RefChem:132845205-974-2dibenzo[b,e][1,4]dioxineDibenzo-para-dioxin

Database identifiers

CAS
262-12-4
PubChem CID
9216
DTXSID
DTXSID8020410
ChEMBL
CHEMBL3184198
ChEBI
CHEBI:28891
UNII
O1B5KJ235I
EC Number
205-974-2
Nikkaji
J34.854F

Properties

Computed structural properties

XLogP
4.4
Topological polar surface area
18.5 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
14
Formal charge
0
Complexity
162

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Other Aromatic Compounds
SpringerMaterials PropertiesBoiling point
LogP · 2 items

log Kow= 4.30

4.19

Color/FormCrystals from methanol
Solubility · 2 items

less than 1 mg/mL at 64 °F (NTP, 1992)

In water, 0.901 mg/l @ 25 °C

DecompositionWhen heated to decomposition it emits acrid smoke and irritating fumes
Melting Point · 3 items

252 to 253 °F (NTP, 1992)

119 °C

119 °C

Vapor Pressure · 3 items

0.000413 [mmHg]

4.12x10-4 mm Hg at 25 °C

0.0004125 [mm Hg] @25 °C

Physical Description · 2 items

Dibenzo-p-dioxin appears as white crystals or crystalline solid. (NTP, 1992)

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

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

DOT LabelClass 9
Fire HazardsFlash point data for this chemical are not available. It is probably combustible. (NTP, 1992)
Health HazardsExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Hazards SummarySee 2,3,7,8-Tetrachlorodibenzo-p-dioxin.
Reactive GroupEthers
Special ReportsBioassay of Dibenzo-p-dioxin for Possible Carcinogenicity (1979) Technical Rpt Series No. 122 DHEW Pub No. (NIH) 79-1377, U.S. Department of Health Education and Welfare, National Cancer Institute, Bethesda, MD 20014
Reactivity ProfileDIBENZO-P-DIOXIN is an ether. Ethers may react violently with strong oxidizing agents. In other reactions, which typically involve the breaking of the carbon-oxygen bond, ethers are relatively inert.
Air and Water ReactionsInsoluble in water.
Hazard Classes and CategoriesAcute Tox. 4 (100%)

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 4 items

Dibenzo-p-dioxin is rapidly metabolized after ip dose to mice into unknown polar products. Liver microsomes (reduced nicotinamide adenine dinucleotide) from mouse, rat, and rabbit also transformed /it/ very efficiently.

In rats, primary hydroxylation of dibenzo-p-dioxins takes place exclusively at 2, 3, 7, or 8 position.

Dioxins were administered to rats. Urine and feces were collected and analyzed. Dibenzo-p-dioxin yielded the 2-hydroxy analog, one methylthio and one dihydroxy analog.

Metabolic transformation of the dibenzo-p-dioxins in the guppy (Poecilia reticulata) appears to involve hydroxylation, probably mediated by the mixed function oxidase system. /Dibenzo-p-dioxins/

Uses & manufacturing

Uses · 3 items

Present in fly ash particulates and emissions from municipal waste incinerators; [HSDB]

Cleaning Furnaces or Flues [Category: Clean]

NOT USED COMMERCIALLY IN THE USA

U.S. Production(1977) NOT PRODUCED COMMERCIALLY IN USA
Methods of ManufacturingUNSUBSTITUTED DIBENZO-PARA-DIOXIN HAS BEEN PREPARED BY HEATING ORTHOCHLOROPHENOL, ANHYDROUS POTASSIUM CARBONATE & COPPER POWDER & REFLUXING RESULTANT MIXTURE WITH AQUEOUS POTASSIUM HYDROXIDE ... /PRODUCT SUBLIMES: SRP/

Applications

UsesDibenzo-p-dioxin is a standard used in environmental testing and research as well as in the studying of PCBs, PCDDs and PCDFs in food.

General DescriptionWhite crystals or crystalline solid.

Upstream & downstream products

Upstream raw materials

2,3,7,8-Tetrachlorodibenzo-p-dioxin

Related reactions

1 records
New reaction record
HRID 337396 reaction equation
HRID 337396As reactantuspto-grants-2014_11

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

White solid; [CAMEO] White flakes; [MSDSonline]

Stability/Shelf LifeThis chemical is stable under normal laboratory conditions. Solutions of this chemical should be stable for 24 hours under normal lab conditions.
Other Experimental PropertiesHydroxyl radical reaction rate constant = 1.20X10-11 cu cm/molecule sec @ 25 °C

Physicochemical properties

Melting point
120 °C · 120 °C
Boiling point
278.5 °C · 278.5°C
Density
1.243 · 1.2430
refractive index
1.625 · 1.6250 (estimate)
storage temp.
Sealed in dry,Room Temperature
form
powder to crystal
color
White to Almost white
Water Solubility
1.4 mg/L · 1.4mg/L(25 ºC)
Henry's Law Constant
8.9 · 8.9×10-2 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
Stability
Stable. Combustible. Incompatible with strong oxidizing agents.
InChI
InChI=1S/C12H8O2/c1-2-6-10-9(5-1)13-11-7-3-4-8-12(11)14-10/h1-8H
InChIKey
NFBOHOGPQUYFRF-UHFFFAOYSA-N
SMILES
O1C2=CC=CC=C2OC2=CC=CC=C12
Toxicology and Carcinogenesis
Bioassay of Dibenzo-p-dioxin for Possible Carcinogenicity (CASRN 262-12-4)
EWG's Food Scores
1 · 1
FDA UNII
1 B5KJ235I · O1B5KJ235I
IARC
3 · 3 (Vol. 69) 1997
EPA Substance Registry System
Dibenzo-p-dioxin (262-12-4)
UNSPSC Code
12352200 · 12352200
Symbol(GHS)
7 · GHS07,GHS09
Signal word
Warning
Hazard statements
302 · H302-H411
Precautionary statements
264 · P264-P270-P273-P301+P312-P391-P501
Hazard Codes
Xn,N
Risk Statements
22 · 22-51/53
Safety Statements
61 · 61
RIDADR
3077 · 3077
WGK Germany
3 · 3
RTECS
3090000 · HP3090000
HS Code
2932.99 · 2932.99.7000
HazardClass
9 · 9
PackingGroup
I
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
4 OralAquatic · Acute Tox. 4 OralAquatic Chronic 2
Hazardous Substances Data
262 · 262-12-4(Hazardous Substances Data)
Toxicity
50 · mouse,LD50,oral,866mg/kg (866mg/kg),Chemosphere. Vol. 19, Pg. 989, 1989.

Safety & protection

Fire FightingFires involving this chemical can be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 item

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Firefighting Hazards...Dioxins may be formed during the combustion of PCBs in fires and explosions. /Dioxins/
Fire Fighting ProceduresFires involving this chemical can be controlled using a dry chemical, carbon dioxide or Halon extinguisher.
Storage ConditionsYou should store this material in a refrigerator.
Cleanup Methods · 1 item

If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Disposal Methods · 1 item

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Isolation and EvacuationExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Protective Action Criteria (PAC) · 3 items

3.7 [mg/m3]

40 [mg/m3]

240 [mg/m3]

Personal Protective Equipment (PPE) · 1 item

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Toxicology

InteractionsOral dibenzo-p-dioxin given to male mice once/wk for 4 wk increased sensitivity to endotoxin, whereas polychlorinated biphenyls did not. Residual polychlorinated biphenyls levels were detected in thymus; dibenzo-p-dioxin was not.
Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 5,200(SRC), determined from a log Kow of 4.3(2) and a regression-derived equation(3), indicates that dibenzo-p-dioxin is expected to be immobile in soil(SRC). Volatilization of dibenzo-p-dioxin from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.1X10-4 atm-cu m/mole(SRC), derived from its vapor pressure, 4.12X10-4 mm Hg(2), and water solubility, 0.901 mg/l(4). However, adsorption to soil is expected to attenuate volatilization(SRC). Dibenzo-p-dioxin is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). Although pure culture studies have shown that dibenzo-p-dioxin can be metabolized(5-8), insufficient data are available to predict the importance of biodegradation in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 5,200(SRC), determined from a log Kow of 4.3(2) and a regression-derived equation(3), indicates that dibenzo-p-dioxin is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.1X10-4 atm-cu m/mole(SRC), derived from its vapor pressure, 4.12X10-4 mm Hg(2), and water solubility, 0.901 mg/l(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 9 hrs and 9 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column(SRC). The estimated volatilization half-life from a model pond is 293 days if adsorption is considered(5). According to a classification scheme(6), an estimated BCF of 410(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Exposure of pure aqueous solutions of dibenzo-p-dioxin in pyrex tubes to outdoor October sunlight resulted in decompositions of up to 6% in three days of exposure(8); however, addition of small amounts of nitrate ion to the aqueous solutions resulted in disappearances of 70% in one day and 92% in three days(8). Although pure culture studies have shown that dibenzo-p-dioxin can be metabolized(9-12), insufficient data are available to predict the importance of biodegradation in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dibenzo-p-dioxin, which has a vapor pressure of 4.12X10-4 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). However, it has been shown that dibenzo-p-dioxin can become irreversibly adsorbed to incinerator stack emissions of fly ash under certain operating conditions(3); therefore, particulate phase dibenzo-p-dioxin may also occur in the ambient environment(SRC). Vapor-phase dibenzo-p-dioxin is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 1.3 days(SRC), calculated from its rate constant of 12X10-12 cu cm/molecule-sec at 25 °C(4). Particulate-phase dibenzo-p-dioxin may be removed from the air by wet and dry deposition(SRC). Dibenzo-p-dioxin has a strong absorption maximum at 290 nm in methanol(5) and has the potential for direct photolysis in the atmosphere(SRC).

Ongoing Test Status · 1 item

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=262-12-4]

Effluent ConcentrationsA laboratory-based simulation of stack emissions from municipal incinerators found dibenzo-p-dioxin was contained in the fly ash(1).
Soil Adsorption/Mobility · 1 item

The Koc of dibenzo-p-dioxin is estimated as 5,200(SRC), using a log Kow of 4.3(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that dibenzo-p-dioxin is expected be immobile in soil(SRC).

Artificial Pollution SourcesDibenzo-p-dioxin is not produced commercially in the USA(SRC). A laboratory-based simulation of stack emissions from municipal incinerators found dibenzo-p-dioxin was contained in the fly ash(1).
Environmental Biodegradation · 1 item

AEROBIC: Pure culture biodegradation studies have shown that dibenzo-p-dioxin is metabolized by Pseudomonas, Beijerinckia, and Sphingomonas species (1-4). Dibenzo-p-dioxin is transformed to the 2-hydroxy-derivative and catechol(3). The specific oxygen uptake rate for dibenzo-p-dioxin by resting cells of Sphingomonas sp. strain SS3 after growth with polyhalogenated diphenyl ethers, 4-fluorodiphenyl ether, 4-chlorodiphenyl ether, and acetate were 29,27,25,and <5 nmoles of O2 consumed per minute per mg protein, respectively(5).

Carcinogen Classification · 6 items

Dibenzo-para-dioxin

Group 3: Not classifiable as to its carcinogenicity to humans

Volume 69: (1997) Polychlorinated Dibenzo-para-dioxins and Polychlorinated Dibenzofurans

1997

1997

Dibenzo-p-dioxin

Environmental Bioconcentration · 1 item

An estimated BCF of 410 was calculated for dibenzo-p-dioxin(SRC), using a log Kow of 4.3(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC).

Volatilization from Water/Soil · 1 item

The Henry's Law constant for dibenzo-p-dioxin is estimated as 1.1X10-4 atm-cu m/mole(SRC) derived from its vapor pressure, 4.12X10-4 mm Hg(1), and water solubility, 0.901 mg/l(2). This Henry's Law constant indicates that dibenzo-p-dioxin is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 9 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 9 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column(SRC). The estimated volatilization half-life from a model pond is 293 days if adsorption is considered(4). Dibenzo-p-dioxin is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

Non-Human Toxicity Excerpts · 5 items

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Groups of 35 male and 35 female Osborne-Mendel rats, five weeks of age, were administered 0 (control), 5000 (low-dose) or 10,000 (high-dose) mg/kg of diet (ppm) dibenzo-para-dioxin (purity 99.5%) in the diet for 110 weeks. Mean body weights of the treated male and female rats were lower that those of the corresponding controls. In the male rats, survival in the control group was lower than in the treated groups (p = 0.011, Tarone test). Survival of high-dose female rats was lower than that of the control and low-dose groups (p = 0.007, Tarone test). At week 90 of the study, 24/35 control and 29/35 rats in each treated group of males were still alive, and 32/35, 31/35 and 20/35 control, low-dose and high-dose female rats, respectively, were still alive. Tumors were not induced in rats of either sex at significantly higher incidence in the treated groups than in the corresponding control groups.

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ ...Groups of 30 male and 30 female Swiss-Webster mice received thrice weekly skin applications of 0.2 ml acetone containing... 80 mg/kg... unsubstituted dibenzo-para-dioxin... . After... 59 wk... 24 male and 24 female mice... were still alive. None of treated mice had skin tumors... 1 female treated with unsubstituted dibenzo-para-dioxin had lymphoma.

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ ...Groups of 50 male and 50 female B6C3F1 mice were fed diets containing 0.5% or 1% unsubstituted dibenzo-para-dioxin... . Numbers of survivors /1%, 39th wk: 48/50 male mice, 29/50 female mice; 0.5%, 34th wk; 50/50 male mice, 39th wk, 49/50 female mice/... hyperplasia of bronchial mucosa... in 1 mouse fed 1% unsubstituted... .

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Mice treated with compounds including dibenzodioxin showed promotion of skin carcinogenesis induced by dimethylbenzanthracene.

For more Non-Human Toxicity Excerpts (Complete) data for DIBENZO-P-DIOXIN (6 total), please visit the HSDB record page.

Evidence for CarcinogenicityEvaluation: There is evidence suggesting the lack of carcinogenicity in experimental animals for dibenzo-p-dioxin. ... Overall Evaluation: Dibenzo-para-dioxin is not classifiable as to its carcinogenicity to humans (Group 3).

Safety data

wgk
3
rtecs
HP3090000
ridadr
3077
hs_code
2932.99.7000
Toxicity
mouse,LD50,oral,866mg/kg (866mg/kg),Chemosphere. Vol. 19, Pg. 989, 1989.
risk_code
22-51/53
Signal word
Warning
Symbol(GHS)
GHS07,GHS09
hazard_code
Xn,N
safety_code
61
hazard_class
9
Storage Class
11 - Combustible Solids
packing_group
I
Hazard statements
H302-H411
Hazard Classifications
Acute Tox. 4 OralAquatic Chronic 2
Precautionary statements
P264-P270-P273-P301+P312-P391-P501
Hazardous Substances Data
262-12-4(Hazardous Substances Data)
1,2,6,7-Tetrachlorodibenzo[1,4]dioxin
1,2-Diiodobenzene
4-Chlorophenol sodium salt
2-Chlorodibenzo-p-dioxin
1-Chlorodibenzo-p-dioxin
2,7-Dichlorodibenzo-p-dioxin
1,2,3,4,6,7,8,9-Octachlorodibenzo-p-dioxin
2,3-Dichlorodibenzo-p-dioxin
1,2-Dinitrobenzene
2-Chlorophenol
2-Bromophenol
Catechol

Downstream products

Monobromodibenzo-para-dioxin

Suppliers91 total

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Additional notes

DefinitionChEBI: Oxanthrene is a heteranthrene, a mancude organic heterotricyclic parent, a polycyclic heteroarene, an oxacycle and a dibenzodioxine.