Dibenzothiophene: Difference between revisions

Dibenzothiophene
Names
	IUPAC name Dibenzothiophene
	Other names Diphenylene sulfide, DBT
Identifiers
CAS Number	132-65-0 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL219828 ;
ChemSpider	2915 ;
ECHA InfoCard	100.004.613
KEGG	D03777 ;
RTECS number	HQ3490550;
UNII	Z3D4AJ1R48 ;
CompTox Dashboard (EPA)	DTXSID0047741 ;
	InChI InChI=1S/C12H8S/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8H Key: IYYZUPMFVPLQIF-UHFFFAOYSA-N ; InChI=1/C12H8S/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8H Key: IYYZUPMFVPLQIF-UHFFFAOYAY;
	SMILES c1ccc2c(c1)c3ccccc3s2;
Properties
Chemical formula	C12H8S
Molar mass	184.26 g/mol
Appearance	Colourless crystals
Density	1.252 g/cm3
Melting point	97-100 °C(lit.)
Boiling point	332-333 °C
Solubility in water	insol.
Solubility in other solvents	benzene and related
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	flammable
Related compounds
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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Revision as of 10:16, 20 May 2011

Dibenzothiophene 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

[1] 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

[2] 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

[1]

[2]

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-Dibenzothiophene 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]].<ref>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}}</ref>
+'''Dibenzothiophene''' is the [[organosulfur compound]] consisting of two [[benzene ring|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]].<ref>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}}</ref>
 ==Synthesis and reactions==
 Dibenzothiophene is prepared by the reaction of [[biphenyl]] with [[sulfur dichloride]] in the presence of [[aluminium trichloride]].<ref>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}}</ref>
-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.
+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==