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Diphenyl sulfide

Organic compound From Wikipedia, the free encyclopedia

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.

Quick facts Names, Identifiers ...
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
C12H10S
Molar mass 186.27 g·mol−1
Appearance Colorless liquid
Odor Unpleasant
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).
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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

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