 | |
 | |
| Names | |
|---|---|
| Preferred IUPAC name Dibenzo[b,d]furan | |
| Identifiers | |
| |
3D model (JSmol) | |
| 121100 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
|
| ECHA InfoCard | 100.004.612 |
| EC Number |
|
| 67825 | |
| KEGG |
|
| UNII | |
| UN number | 3077 |
| |
| |
| Properties | |
| C12H8O | |
| Molar mass | 168.19 g/mol |
| Appearance | white crystalline powder |
| Melting point | 81 to 85 °C (178 to 185 °F; 354 to 358 K) |
| Boiling point | 285 °C (545 °F; 558 K) |
| Insoluble | |
| Hazards | |
| GHS labelling: | |
  | |
| Warning | |
| H302,H312,H332,H411 | |
| P273,P391,P501 | |
| Related compounds | |
Related compounds | Furan Benzofuran Dibenzodioxin Dibenzothiophene Carbazole Polyozellin (compound with akernel with two dibenzofurans that share the same benzene ring) |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Dibenzofuran is aheterocyclicorganic compound with thechemical structure shown at right. It is anaromatic compound that has twobenzene rings fused to a centralfuran ring. All the numberedcarbon atoms have ahydrogen atom bonded to each of them. It is a volatile white solid that is soluble in nonpolar organic solvents. It is obtained fromcoal tar, where it exists as a 1% component.[1]
Dibenzofuran is thermally robust with a convenient liquid range. These properties, together with its low toxicity, are exploited by the use of DBF as a heat transfer agent.[1]
It undergoes electrophilic reactions, such as halogenation andFriedel-Crafts reactions. Reaction of DBF with butyl lithium results in dilithiation.[2]
Dibenzofuran is the precursor to the drug furobufen byFriedel-Crafts reaction withsuccinic anhydride.
Dibenzofuran is a relatively non-toxic compound as evidenced by rats being unaffected after a 200-day diet consisting of 0.025 – 0.4% of DBF.[1] Thepolychlorinated dibenzofurans are however among the potentially toxicdioxins and dioxin-like compounds.
Dibenzofuran is cited in the United States Clean Air Act 1990 Amendments -Hazardous Air Pollutants as a volatile hazardous air pollutant of potential concern. The Superfund Amendment Reauthorization Act (SARA) Section 110 placed dibenzofuran on the revisedAgency for Toxic Substances and Disease Registry (ATSDR) priority list of hazardous substances to be the subject of a toxicological profile. The listing was based on the substance's frequency of occurrence at Comprehensive Environmental Response, Compensation, and Liability Act (CERCLA) National Priorities List sites, its toxicity, and/or its potential for human exposure.[3]
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