4,6-Dimethyldibenzothiophene

4,6-Dimethyldibenzothiophene
Names
	Other names 4,6-DMDBT
Identifiers
CAS Number	1207-12-1;
3D model (JSmol)	Interactive image;
ChemSpider	1064783;
EC Number	214-894-7;
PubChem CID	1268103;
	InChI InChI=1S/C14H12S/c1-9-5-3-7-11-12-8-4-6-10(2)14(12)15-13(9)11/h3-8H,1-2H3 Key: MYAQZIAVOLKEGW-UHFFFAOYSA-N;
	SMILES CC1=C2C(=CC=C1)C3=CC=CC(=C3S2)C;
Properties
Chemical formula	C14H12S
Molar mass	212.31 g·mol−1
Appearance	white solid
Density	1.18 g/cm3
Melting point	153–157 °C (307–315 °F; 426–430 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302
Precautionary statements	P264, P270, P301+P317, P330, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

4,6-Dimethyldibenzothiophene is an organosulfur compound with the formula (C₆H₃CH₃)₂S. It is one of several dimethyl derivatives of benzothiophene. The compound is of particular interest as an organosulfur contaminant in petroleum that is recalcitrant. Both methyl groups shield the sulfur center from desulfurization.^[2]^[3]

The compound can be oxidized to the sulfoxide with hydrogen peroxide.^[4] Many methods for synthesis of this compound have been described. Often the methods proceed via derivatives of diphenyl sulfide.^[5]

References

^ "4,6-Dimethyldibenzothiophene". pubchem.ncbi.nlm.nih.gov.
^ Song, Chunshan; Ma, Xiaoliang (2003). "New Design Approaches to Ultra-Clean Diesel Fuels by Deep Desulfurization and Deep Dearomatization". Applied Catalysis B: Environmental. 41 (1–2): 207–238. doi:10.1016/s0926-3373(02)00212-6.
^ Gates, B.C.; Topsøe, Henrik (1997). "Reactivities in Deep Catalytic Hydrodesulfurization: Challenges, Opportunities, and the Importance of 4-Methyldibenzothiophene and 4,6-Dimethyldibenzothiophene". Polyhedron. 16 (18): 3213–3217. doi:10.1016/s0277-5387(97)00074-0.
^ Sato, Kazuhiko; Hyodo, Mamoru; Aoki, Masao; Zheng, Xiao-Qi; Noyori, Ryoji (2001). "Oxidation of Sulfides to Sulfoxides and Sulfones with 30% Hydrogen Peroxide under Organic Solvent- and Halogen-Free Conditions". Tetrahedron. 57 (13): 2469–2476. doi:10.1016/s0040-4020(01)00068-0.
^ Meille, Valérie; Schulz, Emmanuelle; Lemaire, Marc; Faure, René; Vrinat, Michel (1996). "An Efficient Synthesis of Pure 4,6-Dimethyldibenzothiophene". Tetrahedron. 52 (11): 3953–3960. doi:10.1016/S0040-4020(96)00041-5.

[1] "4,6-Dimethyldibenzothiophene". pubchem.ncbi.nlm.nih.gov.

[2] Song, Chunshan; Ma, Xiaoliang (2003). "New Design Approaches to Ultra-Clean Diesel Fuels by Deep Desulfurization and Deep Dearomatization". Applied Catalysis B: Environmental. 41 (1–2): 207–238. doi:10.1016/s0926-3373(02)00212-6.

[3] Gates, B.C.; Topsøe, Henrik (1997). "Reactivities in Deep Catalytic Hydrodesulfurization: Challenges, Opportunities, and the Importance of 4-Methyldibenzothiophene and 4,6-Dimethyldibenzothiophene". Polyhedron. 16 (18): 3213–3217. doi:10.1016/s0277-5387(97)00074-0.

[4] Sato, Kazuhiko; Hyodo, Mamoru; Aoki, Masao; Zheng, Xiao-Qi; Noyori, Ryoji (2001). "Oxidation of Sulfides to Sulfoxides and Sulfones with 30% Hydrogen Peroxide under Organic Solvent- and Halogen-Free Conditions". Tetrahedron. 57 (13): 2469–2476. doi:10.1016/s0040-4020(01)00068-0.

[5] Meille, Valérie; Schulz, Emmanuelle; Lemaire, Marc; Faure, René; Vrinat, Michel (1996). "An Efficient Synthesis of Pure 4,6-Dimethyldibenzothiophene". Tetrahedron. 52 (11): 3953–3960. doi:10.1016/S0040-4020(96)00041-5.

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