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
ECHA InfoCard	100.004.613
EC Number	205-072-9
KEGG	D03777^Y
PubChem CID	3023
RTECS number	HQ3490550
UNII	Z3D4AJ1R48^Y
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^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/cm^3
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
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H302, H311, H315, H331, H332, H410
Precautionary statements	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). Y verify (what is ^YN ?) 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

1. 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.
2. 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.
3. 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.
4. Bhanuchandra, M.; Yorimitsu Hideki. "Dibenzothiophene 5,5-dioxide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn02046.