Dibenzothiophene

Dibenzothiophene
Names
	IUPAC name Dibenzothiophene
	Other names Diphenylene sulfide, DBT
Identifiers
CAS Number	132-65-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:23681 ;
ChEMBL	ChEMBL219828 ;
ChemSpider	2915 ;
ECHA InfoCard	100.004.613
EC Number	205-072-9;
KEGG	D03777 ;
PubChem CID	3023;
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 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
Main hazards	flammable
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H302, H311, H315, H331, H332, H400, H410
GHS precautionary statements	P261, P264, P270, P271, P273, P280, P301+312, P302+352, P304+312, P304+340, P311, P312, P321, P322, P330, P332+313, P361, P362, P363, P391, P403+233, 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).
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	Infobox references

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 chloride.[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 butyllithium, 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