Chemistry:Dibenzothiophene

Dibenzothiophene

Names
Preferred IUPAC name Dibenzo[b,d]thiophene
Other names Diphenylene sulfide, DBT
Identifiers
CAS Number	132-65-0 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:23681 Y
ChEMBL	ChEMBL219828 Y
ChemSpider	2915 Y
EC Number	205-072-9
KEGG	D03777 Y
PubChem CID	3023
RTECS number	HQ3490550
UNII	Z3D4AJ1R48 Y
InChI InChI=1S/C12H8S/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8H Y Key: IYYZUPMFVPLQIF-UHFFFAOYSA-N Y 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, toxic
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H301, H302, H311, H315, H331, H332, 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

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Dibenzothiophene (DBT, diphenylene sulfide) 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 disubstituted derivative 4,6-dimethyldibenzothiophene are problematic impurities in petroleum.

Synthesis and reactions

Dibenzothiophene is prepared by the reaction of biphenyl with sulfur dichloride in the presence of aluminium chloride.

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.