Dibenzofuran

Dibenzofuran

Identifiers
CAS Number	132-64-9
ChEBI	CHEBI:28145
ChEMBL	ChEMBL277497
ChemSpider	551
Jmol interactive 3D	Image
KEGG	C07729
PubChem	568
InChI InChI=1S/C12H8O/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8H Key: TXCDCPKCNAJMEE-UHFFFAOYSA-N InChI=1/C12H8O/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8H Key: TXCDCPKCNAJMEE-UHFFFAOYAX
SMILES o2c1ccccc1c3c2cccc3
Properties
Chemical formula	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)
Solubility in water	Insoluble
Hazards
R-phrases	R51/53
S-phrases	S24/25 S29 S61
Related compounds
Related compounds	Furan Benzofuran Dibenzodioxin Dibenzothiophene Carbazole Polyozellin (compound with a kernel with two dibenzofurans that share the same benzene ring)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Dibenzofuran is a heterocyclic organic compound with the chemical structure shown at right. It is an aromatic compound that has two benzene rings fused to a central furan ring. All the numbered carbon atoms have a hydrogen atom bonded to each of them (not shown in the image). It is a volatile white solid that is soluble in nonpolar organic solvents. It is obtained from coal tar, where it exists as a 1% component.^[1]

Reactions

Dibenzofuran is extremely stable, and this property is exploited by the use of DBF as a heat transfer agent.

It undergoes electrophilic reactions, such as halogenation and Friedel-Crafts reactions. Reaction of DBF with bultyl lithium results in dilithiation.^[2]

Dibenzofuran is needed to make furobufen by Friedel-Crafts reaction with succinic anhydride.

Safety

Dibenzofuran is a relatively non-toxic compound. The polychlorinated dibenzofurans are however controversial and potentially dangerous.^[3]

References

1. Gerd Collin and Hartmut Höke "Benzofurans" in Ullmann's Encyclopedia of Industrial Chemistry, 2007, Wiley-VCH, Weinheim. doi:10.1002/14356007.l03_l01
2. Ulrich Iserloh, Yoji Oderaotoshi, Shuji Kanemasa, and Dennis P. Curran "Synthesis of (R,R)-4,6-Dibenzofurandiyl-2,2'-Bis (4-Phenyloxazoline) (DBFOX/PH) – A Novel Trridentate Ligand" Org. Synth. 2003, 80, 46.
3. Reference needed