Diphenyl sulfide

Diphenyl sulfide
Names
	IUPAC name Phenylsulfanylbenzene
Identifiers
CAS Number	139-66-2;
3D model (JSmol)	Interactive image;
Abbreviations	Ph2S
Beilstein Reference	1907932
ChEBI	CHEBI:38959;
ChEMBL	ChEMBL219876;
ChemSpider	8436;
ECHA InfoCard	100.004.884
EC Number	205-371-4;
UNII	B5P3Y93MNR;
CompTox Dashboard (EPA)	DTXSID8044383;
	InChI InChI=1S/C12H10S/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10H Key: LTYMSROWYAPPGB-UHFFFAOYSA-N;
	SMILES C1=CC=C(C=C1)SC2=CC=CC=C2;
Properties
Chemical formula	(C6H5)2S
Molar mass	186.27 g·mol−1
Appearance	Colorless liquid
Density	1.113 g/cm3 (20 °C); Vapor: 6.42 (air = 1.0)
Melting point	−25.9 °C (−14.6 °F; 247.2 K)
Boiling point	296 °C (565 °F; 569 K)
Solubility in water	insoluble
Solubility	Soluble in diethyl ether, benzene, carbon disulfide.
Vapor pressure	0.01 hPa at 25 °C
Refractive index (nD)	1.6327
Viscosity	Dynamic:; 21.45 mPa·s at 20 °C; 18.4 mPa·s at 40 °C; Kinematic:; 19.43 mm2/s at 20 °C; 16.7 mm2/s at 40 °C;
Structure
Molecular shape	Bent on the sulfur atom
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H315, H319, H410
Precautionary statements	P264, P270, P273, P280, P301+P312, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P362+P364, P391, P501
Flash point	113 °C (235 °F)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	300 to 2000 mg/kg (oral, female rat); 5000 mg/kg (dermal, female rat); 11300 μL/kg (dermal, rabbit); 490 μL/kg (oral, rat); 545 mg/kg (oral, rat); 12600 mg/kg (dermal, rabbit);
Related compounds
Related compounds	Diphenyl ether; Diphenyl selenide; Diphenyl telluride; Diphenyl disulfide; Thiophenol; Diphenyl sulfone;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Diphenyl sulfide is an organosulfur compound with the chemical formula (C₆H₅)₂S, often abbreviated as Ph₂S, where Ph stands for phenyl. It is a colorless liquid with an unpleasant odor. Diphenyl sulfide is an aromatic sulfide. The molecule consists of two phenyl groups attached to a sulfur atom.

Synthesis, reactions, occurrence

Many methods exist for the preparation of diphenyl sulfide. It arises by a Friedel-Crafts-like reaction of sulfur monochloride and benzene.^[4] Diphenyl sulfide and its analogues can also be produced by coupling reactions using metal catalysts.^[5] It can also be prepared by reduction of diphenyl sulfone.^[6]

Diphenyl sulfide is a product of the photodegradation of the fungicide edifenphos.^[7]

Diphenyl sulfide is a precursor to triaryl sulfonium salts, which are used as photoinitiators. The compound can be oxidized to the sulfoxide with hydrogen peroxide.^[8]

References

^ "3". CRC Handbook of Chemistry and Physics (90 ed.). 2010. p. 220.
^ ^a ^b "GESTIS-Stoffdatenbank".
^ "Diphenyl sulfide".
^ Hartman, W. W.; Smith, L. A.; Dickey, J. B. (1934). "Diphenyl Sulfide". Organic Syntheses. 14: 36. doi:10.15227/orgsyn.014.0036.
^ Lian, Zhong; Bhawal, Benjamin N.; Yu, Peng; Morandi, Bill (2017). "Palladium-catalyzed carbon-sulfur or carbon-phosphorus bond metathesis by reversible arylation". Science. 356 (6342): 1059–1063. Bibcode:2017Sci...356.1059L. doi:10.1126/science.aam9041. PMID 28596362. S2CID 206657928.
^ Krafft, F.; Vorster, W. (1893). "Ueber Umwandlung des Diphenylsulfons in Diphenylsulfid und Diphenylselenid". Berichte der Deutschen Chemischen Gesellschaft. 26 (3): 2813–2822. doi:10.1002/cber.18930260393.
^ Murai, Toshinobu (1977). "Photodecomposition of O -Ethyl S , S -Diphenyl Phosphorodithiolate (Edifenphos)". Agricultural and Biological Chemistry. 41: 71–77. doi:10.1080/00021369.1977.10862468.
^ 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.

[1] "3". CRC Handbook of Chemistry and Physics (90 ed.). 2010. p. 220.

[gestis-2] "GESTIS-Stoffdatenbank".

[3] "Diphenyl sulfide".

[4] Hartman, W. W.; Smith, L. A.; Dickey, J. B. (1934). "Diphenyl Sulfide". Organic Syntheses. 14: 36. doi:10.15227/orgsyn.014.0036.

[5] Lian, Zhong; Bhawal, Benjamin N.; Yu, Peng; Morandi, Bill (2017). "Palladium-catalyzed carbon-sulfur or carbon-phosphorus bond metathesis by reversible arylation". Science. 356 (6342): 1059–1063. Bibcode:2017Sci...356.1059L. doi:10.1126/science.aam9041. PMID 28596362. S2CID 206657928.

[wiley-6] Krafft, F.; Vorster, W. (1893). "Ueber Umwandlung des Diphenylsulfons in Diphenylsulfid und Diphenylselenid". Berichte der Deutschen Chemischen Gesellschaft. 26 (3): 2813–2822. doi:10.1002/cber.18930260393.

[7] Murai, Toshinobu (1977). "Photodecomposition of O -Ethyl S , S -Diphenyl Phosphorodithiolate (Edifenphos)". Agricultural and Biological Chemistry. 41: 71–77. doi:10.1080/00021369.1977.10862468.

[8] 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.

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