Dibenzothiophene
Appearance
Names | |
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IUPAC name
Dibenzothiophene
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Other names
Diphenylene sulfide, DBT
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Identifiers | |
3D model (JSmol)
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.004.613 |
EC Number |
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KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C12H8S | |
Molar mass | 184.26 g/mol |
Appearance | Colourless crystals |
Density | 1.252 g/cm3 |
Melting point | 97 to 100 °C (207 to 212 °F; 370 to 373 K) (lit.) |
Boiling point | 332 to 333 °C (630 to 631 °F; 605 to 606 K) |
insol. | |
Solubility in other solvents | benzene and related |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
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flammable |
GHS labelling: | |
Danger | |
H302, H311, H315, H331, H332, H410 | |
P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P312, P304+P340, P311, P312, P321, P322, P330, P332+P313, P361, P362, P363, P391, P403+P233, P405, P501 | |
Related compounds | |
Related compounds
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Thiophene anthracene benzothiophene |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dibenzothiophene (DBT) is the organosulfur compound consisting of two benzene rings fused to a central thiophene ring. It is a colourless solid that is chemically somewhat similar to anthracene. This tricyclic heterocycle, and especially its alkyl substituted derivatives, occur widely in heavier fractions of petroleum.[1]
Synthesis and reactions
Dibenzothiophene is prepared by the reaction of biphenyl with sulfur dichloride in the presence of aluminium trichloride.[2]
Reduction with lithium results in scission of one C-S bond. S-oxidation occurs to give the sulfone, which is more labile than the parent dibenzothiophene. With butyl lithium, this heterocycle undergoes stepwise lithiation at the 4- and 6- positions.
References
- ^ Teh C. Ho "Deep HDS of diesel fuel: chemistry and catalysis" Catalysis Today 2004, Volume 98, pp. 3-18. doi:10.1016/j.cattod.2004.07.048
- ^ L. H. Klemm, Joseph J. Karchesy "Dibenzothiophene from biphenyl and derivatives" Journal of Heterocyclic Chemistry, 1978, Volume 15 Issue 4, Pages 561 - 563. doi:10.1002/jhet.5570150407