Diphenyl sulfide

Diphenyl sulfide is an organic 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, whose molecule consists of two phenyl groups attached to a sulfur atom.[1] This chemical is metabolite of the fungicide edifenphos. Diphenyl sulfide can be prepared by reduction of diphenyl sulfone.[8]

Diphenyl sulfide
Diphenyl sulfide molecule
Names
IUPAC name
Phenylsulfanylbenzene[1]
Other names
  • (Phenylsulfanyl)benzene[1]
  • Diphenyl sulfide[1]
  • Diphenyl thioether[1]
  • Diphenylsulfane[1]
  • Phenyl sulfide[1]
  • Phenylthiobenzene[1]
Identifiers
3D model (JSmol)
Abbreviations Ph2S
1907932
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.884
EC Number
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[1][2][3]
Odor Unpleasant[1][3]
Density 1.113 g/cm3 (20 °C)[4][5]
Vapor: 6.42 (air = 1.0)[6][3]
Melting point −40 °C (−40 °F; 233 K)[4][3]
Boiling point 296 °C (565 °F; 569 K)[4][3]
Practically insoluble[4][3]
Solubility Soluble in diethyl ether, benzene, carbon disulfide.[2]
Vapor pressure 0.01 hPa at 25 °C[4][3]
1.6327[7]
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
[4][3]
Structure
Bent on the sulfur atom
Hazards[1][4][3]
Occupational safety and health (OHS/OSH):
Main hazards
 Very toxic to aquatic life with long lasting effects, severe skin and eye corrosion, explosive reaction with strong oxidizing agents, forms explosive mixtures with air[1]
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)[4]
Lethal dose or concentration (LD, LC):
  • 300 to 2000 mg/kg (oral, female rat)[4]
  • 5000 mg/kg (dermal, female rat)[4]
  • 11300 μL/kg (dermal, rabbit)[1][6]
  • 490 μL/kg (oral, rat)[1][6]
  • 545 mg/kg (oral, rat)[3]
  • 12600 mg/kg (dermal, rabbit)[3]
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Uses

Diphenyl sulfide is used as a chemical for triarylsulfonium photoinitiator, intermediates for production of metal extractants, agrochemicals and catalysts.[2]

Safety

Diphenyl sulfide is sensitive to light. It is flammable, and upon catching fire, emits irritating and toxic fumes and gases of oxides of carbon and sulfur (like carbon monoxide CO, carbon dioxide CO2 and sulfur dioxide SO2). The fire of diphenyl sulfide may be extinguished with dry ice (carbon dioxide) or water spray. The vapor of diphenyl sulfide is heavier than air and may spread along floors. It forms explosive mixtures with air, especially upon heating. It may react violently with strong oxidizing agents, acids, acyl chlorides and acid anhydrides.[1][4][6][3]

Diphenyl sulfide irritates skin, mucous membranes and may cause severe eye injury by corrosion. After contact with eyes, it is recommended to remove contact lenses and rinse eyes with a plenty of water immediately. If this chemical is accidentally swallowed, the victim must drink at most two glasses of water immediately. It is required to consult a doctor immediately.[1][4]

References
  1. "Diphenyl sulfide".
  2. https://www.thermofisher.com/order/catalog/product/A11114.22
  3. "GESTIS-Stoffdatenbank".
  4. https://www.sigmaaldrich.com/GB/en/sds/aldrich/p35316
  5. "3". CRC Handbook of Chemistry and Physics (90 ed.). 2010. p. 220.
  6. https://www.fishersci.com/store/msds?partNumber=AAA1111414&productDescription=DIPHENYL+SULFIDE+25G&vendorId=VN00024248&countryCode=US&language=en
  7. "SX2275000 | C12H10S | ChemSpider".
  8. 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.
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