Diphenyl sulfide
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IUPAC name Phenylsulfanylbenzene | |
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3D model (JSmol) |
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Abbreviations | Ph2S |
Beilstein Reference | 1907932 |
ChEBI |
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ChemSpider |
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ECHA InfoCard | 100.004.884 ![]() |
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InChI
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Properties | |
Chemical formula | (C6H5)2S |
Molar mass | 186.27 g·mol−1 |
Appearance | Colorless liquid |
Density | 1.113 g/cm3 (20 °C)[1] 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[2] |
Refractive index (nD) | 1.6327 |
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Structure | |
Bent on the sulfur atom | |
Hazards | |
GHS labelling: | |
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Warning | |
H302, H315, H319, H410 | |
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) |
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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 triarylsulfonium 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.