Diphenyl sulfide

Diphenyl sulfide
Diphenyl sulfide molecule
Names
IUPAC name
Phenylsulfanylbenzene
Identifiers
3D model (JSmol)
Abbreviations Ph2S
1907932
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.884 Edit this at Wikidata
EC Number
  • 205-371-4
UNII
  • InChI=1S/C12H10S/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12/h1-10H
    Key: LTYMSROWYAPPGB-UHFFFAOYSA-N
  • C1=CC=C(C=C1)SC2=CC=CC=C2
Properties
(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)
insoluble
Solubility Soluble in diethyl ether, benzene, carbon disulfide.
Vapor pressure 0.01 hPa at 25 °C[2]
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
Bent on the sulfur atom
Hazards
GHS labelling:
GHS07: Exclamation markGHS09: Environmental hazard
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)
Lethal dose or concentration (LD, LC):
  • 300 to 2000 mg/kg (oral, female rat)
  • 5000 mg/kg (dermal, female rat)
  • 11300 μL/kg (dermal, rabbit)[3]
  • 490 μL/kg (oral, rat)
  • 545 mg/kg (oral, rat)
  • 12600 mg/kg (dermal, rabbit)[2]
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

  1. ^ "3". CRC Handbook of Chemistry and Physics (90 ed.). 2010. p. 220.
  2. ^ a b "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.
  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.