Dibenzofuran

Dibenzofuran Basic information
Chemical reactivity
Product Name:Dibenzofuran
Synonyms:Dibenzofuran,Diphenylene oxide;Dibenzofuran 2g [132-64-9];8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(9),2,4,6,10,12-hexaene;Industry fluorene oxide;Dibenzo[b,d]furan (purity);2,2’-biphenyleneoxide;2,2’-biphenylyleneoxide;2,2'-Biphenylene oxide
CAS:132-64-9
MF:C12H8O
MW:168.19
EINECS:205-071-3
Product Categories:synthetic dyes, medicines and perfume;Benzofurans;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Alpha Sort;D;DAlphabetic;DIA - DIC;Volatiles/ Semivolatiles;Fluorene Derivatives;Organics;Furan&Benzofuran;Intermediates of Dyes and Pigments;Alphabetic
Mol File:132-64-9.mol
Dibenzofuran Structure
Dibenzofuran Chemical Properties
Melting point 80-82 °C (lit.)
Boiling point 154-155 °C/20 mmHg (lit.)
density 1,3 g/cm3
vapor pressure 2.48 x 10-3 mmHg at 25 °C (Chirico et al., 1990)
refractive index 1.6480
Fp 130 °C
storage temp. Store below +30°C.
solubility Insoluble in wate(<1 mg/mL). Soluble in nonpolar organic solvents.
form neat
color White to Almost white
Water Solubility <0.1 g/100 mL at 20 ºC
BRN 121100
Henry's Law Constant5.82 x 10-5 atm?m3/mol at 25 °C (approximate - calculated from water solubility and vapor pressure)
InChIKeyTXCDCPKCNAJMEE-UHFFFAOYSA-N
CAS DataBase Reference132-64-9(CAS DataBase Reference)
NIST Chemistry ReferenceDibenzofuran(132-64-9)
EPA Substance Registry SystemDibenzofuran (132-64-9)
Safety Information
Hazard Codes N,Xn,T,F
Risk Statements 51/53-22-39/23/24/25-23/24/25-11-20/21/22-63-43-36/37/38-45-67-40
Safety Statements 22-24/25-61-29-45-36/37-16-7-7/9-23-53
RIDADR UN3077
WGK Germany 3
RTECS HP4430000
TSCA Yes
HazardClass 9
PackingGroup III
HS Code 29329995
Hazardous Substances Data132-64-9(Hazardous Substances Data)
ToxicityHeitmuller et al. (1981) reported a NOEC of 1.0 ppm.
MSDS Information
ProviderLanguage
Diphenylene oxide English
SigmaAldrich English
ACROS English
ALFA English
Dibenzofuran Usage And Synthesis
Chemical reactivityChemical reactivity is analogous to benzo[b]furan, especially electrophilic substitution reactions such as nitration, halogenation, sulfonation, acylation, and alkylation reactions. The preferred positions are 2 and 2,8, while nitration takes place at the 3- and 3,8-positions depending on the electrophilicity of the functionality.
DescriptionDioxins and furans, two well-known environmental pollutants, are extremely toxic to humans and many other species. Dibenzofurans are released into the air from combustion sources, and are listed as pollutants of concern due to its persistence in the environment, potential to bioaccumulate, and toxicity to humans and the environment. These compounds, when adsorbed on soils or other substrates, are highly persistent under normal environmental conditions. The Office of Environmental Health Hazard Assessment reviews risk assessments submitted under the Air Toxics ‘Hot Spots’ Program (AB 2588) in which chlorinated dibenzo-p-dioxins and dibenzofurans are listed. Chlorinated dibenzofurans were calculated as total 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) equivalents in the AB 2588 risk assessments. Dibenzofuran is cited in the Clean Air Act 1990 Amendments – Hazardous Air Pollutants as a volatile hazardous air pollutant of potential concern. The Superfund Amendment Reauthorization Act Section 110 placed dibenzofuran on the revised Agency for Toxic Substances and Disease Registry priority list of hazardous substances to be the subject of a toxicological profile. Dibenzofuran is also listed in the Massachusetts Substance List for Right to Know Law, the New Jersey Department of Health Hazard Right to Know Program Hazardous Substance List, the Pennsylvania Department of Labor and Industry Hazardous Substance List, and the California’s Air Toxics ‘Hot Spots’ List (Assembly Bill 2588).
Chemical Propertieswhite to light yellow crystal powde
Chemical PropertiesDibenzofuran is a white crystalline powder.
Physical propertiesColorless crystals having a creosote-like odor. The least detectable odor threshold concentration in water at 60 °C was 2 μg/L (Alexander et al., 1982).
UsesResearch chemical. Derived from industrial and experimental coal gasification operations where the maximum concentration detected in coal gas tar streams was 12 mg/m3 (Cleland, 1981).
UsesDibenzofuran is an industrial chemical or by-product, and is used as an insecticide, in the production of PVC, industrial bleaching and incineration.
UsesApplications for GC (Gas Chromatography) and LC (Liquid Chromatography) Analysis. Dibenzofuran as the model substrate in culture procedures.
DefinitionChEBI: A mancude organic heterotricyclic parent that consists of a furan ring flanked by two benzene rings ortho-fused across the 2,3- and 4,5-positions.
Synthesis Reference(s)Journal of the American Chemical Society, 81, p. 487, 1959 DOI: 10.1021/ja01511a056
The Journal of Organic Chemistry, 40, p. 1365, 1975 DOI: 10.1021/jo00897a048
General DescriptionColorless white crystalline solid.
Air & Water ReactionsInsoluble in water.
Reactivity ProfileDibenzofuran is sensitive to prolonged exposure to light .
Fire HazardFlash point data for Dibenzofuran are not available. Dibenzofuran is probably combustible.
Potential ExposureThis material is used as an insecticide and in organic synthesis to make other chemicals. It is derived from coal tar creosote.
SourceBased on laboratory analysis of 7 coal tar samples, dibenzofuran concentrations ranged from 170 to 4,000 ppm (EPRI, 1990).
Schauer et al. (1999) reported dibenzofuran in diesel fuel at a concentration of 29 μg/g and in a diesel-powered medium-duty truck exhaust at an emission rate of 28.7 μg/km.
Gas-phase tailpipe emission rates from gasoline-powered automobiles with and without catalytic converters were 5.5 and 42.2 μg/km, respectively (Schauer et al., 2002).

Environmental fateBiological. Dibenzofuran was oxidized by salicylate-induced cells of Pseudomonas sp. strain 9816/11 and isopropyl-β-D-thiogalactopyranoside-induced cells of Escherichia coli JM109(DE3) (pDTG141) to (1R,2S)-cis-1,2-dihydroxy-1,2-dihydrodibenzofuran (60–70% yield) and (3S,4R)- cis-3,4-dihydroxy-3,4-dihydrodibenzofuran (30–40% yield) (Resnick and Gibson, 1996).
Soil. The estimated half-lives of dibenzofuran in soil under aerobic and anaerobic conditions were 7 to 28 and 28 to 112 d, respectively (Lee et al., 1984).
Groundwater. Based on aerobic acclimated and unacclimated groundwater die away test data, the estimated half-life of dibenzofuran in groundwater ranged from 8.54 to 34.9 d (Lee et al., 1984).
Photolytic. The estimated half-life for the reaction of dibenzofuran with OH radicals in the atmosphere ranged from 1.9 to 19 h (Atkinson, 1987).
Chemical/Physical. It was suggested that the chlorination of dibenzofuran in tap water accounted for the presence of chlorodibenzofuran (Shiraishi et al., 1985).
Dibenzofuran will not hydrolyze because it has no hydrolyzable functional group (Kollig, 1995).




ShippingUN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.
Purification MethodsDissolve dibenzofuran in diethyl ether, then shake it with two portions of aqueous NaOH (2M), wash it with water, separate and dry (MgSO4) it. After evaporating the ether, dibenzofuran is crystallised from aqueous 80% EtOH and then dried under vacuum. [Cass et al. J Chem Soc 1406 1958.] High purity material is obtained by zone refining. [Beilstein 17 V 234.]
Toxicity evaluationDibenzofuran is a white crystalline solid. It is not soluble in water, but soluble in organic solvents like alcohol, acetone, ether, benzene, and acetic acid. Its boiling point is 287°C, melting point is 86°C, and specific gravity is 1.0886. Its octanol/ water partition coefficient is 4.12.
Presence of dibenzofuran in coal tar, oil and its uses may result in its release to the environment through various waste streams. It has very low to no mobility in soil and degrades in soil. It dissolves in water as well as volatilizes. As a gas phase in the atmosphere, it reacts with photochemically produced hydroxy radicals. It is biodegraded rapidly at contaminated sites by the microorganisms present; otherwise its biodegradation is relatively slow. It adsorbs very strongly to sediment and particulate matter in the water column. It has a potential to bioconcentrate in aquatic organisms.
IncompatibilitiesThis material is used as an insecticide and in organic synthesis to make other chemicals. It is derived from coal tar creosote.
Waste DisposalIn accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed prop- erly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office.
Dibenzofuran, 1,2,3,4-tetrachloro Dibenzofuran-2-sulphonic acid,DIBENZOFURAN-2-SULFONIC ACID,DIBENZOFURAN-2-SULPHONIC ACID MONOHYDRATE FURFURYL ALCOHOL RESIN DIBENZOFURAN (13C12),13C12-DIBENZOFURAN (Diethoxymethyl)diphenylphosphine oxide Dbf4 protein Iron oxide DIBENZOFURAN-3-YLAMINE 2-dibenzofuranamine 3-AMINO-2-METHOXYDIBENZOFURAN BENZO[B]NAPHTHO[1,2-D]FURAN DIBENZOFURAN-4-CARBOXALDEHYDE 97 2-hydroxydibenzofuran-3-carboxylic acid 1-DIBENZOFURAN-2-YL-ETHANONE Bisomer DBF,RC Comonomer DBF,Staflex DBF DIBENZOFURAN-2-YL-ETHYL-AMINE (6,7,8,9-TETRAHYDRO-DIBENZOFURAN-2-YLOXY)-ACETIC ACID DIBENZOFURAN-4-CARBOXYLIC ACID

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