Dibenzothiophene
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Names | |
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Preferred IUPAC name Dibenzo[b,d]thiophene | |
Other names Diphenylene sulfide, DBT | |
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ECHA InfoCard | 100.004.613 ![]() |
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Properties | |
Chemical formula | 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) |
Solubility in water | insol. |
Solubility in other solvents | benzene and related |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards | flammable, toxic |
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Danger | |
H301, 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 | Thiophene Anthracene Benzothiophene Dibenzofuran |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). ![]() ![]() ![]() Infobox references |
Dibenzothiophene (DBT, diphenylene sulfide) is the organosulfur compound consisting of two benzene rings fused to a central thiophene ring. It has the chemical formula C12H8S. It is a colourless solid that is chemically somewhat similar to anthracene. This tricyclic heterocycle, and especially its disubstituted derivative 4,6-dimethyldibenzothiophene are problematic impurities in petroleum.[1]
Synthesis and reactions
Dibenzothiophene is prepared by the reaction of biphenyl with sulfur dichloride in the presence of aluminium chloride.[2]
Reduction with lithium results in scission of one C-S bond. With butyllithium, this heterocycle undergoes stepwise lithiation at the 4-position. S-oxidation with peroxides gives the sulfoxide.[3]
Dibenzothiophene is electron-rich, and naturally undergoes aromatic substitution para to the sulfide. Oxidation to the sulfoxide or sulfone leaves the compound electron poor, and substitution occurs at the meta position instead.[4]
References
- ^ Ho, Teh C. (2004). "Deep HDS of Diesel Fuel: Chemistry and Catalysis". Catalysis Today. 98 (1–2): 3–18. doi:10.1016/j.cattod.2004.07.048.
- ^ Klemm, L. H.; Karchesy, Joseph J. (1978). "The Insertion and Extrusion of Heterosulfur Bridges. VIII. Dibenzothiophene from Biphenyl and Derivatives". Journal of Heterocyclic Chemistry. 15 (4): 561–563. doi:10.1002/jhet.5570150407.
- ^ Waldecker, Bernd; Kafuta, Kevin; Alcarazo, Manuel (2019). "Preparation of 5-(Triisopropylalkynyl) dibenzo[b,d]thiophenium triflate". Organic Syntheses. 96: 258–276. doi:10.15227/orgsyn.096.0258. S2CID 239319277.
- ^ Bhanuchandra, M.; Yorimitsu Hideki. "Dibenzothiophene 5,5-dioxide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn02046.