Dibenzyl sulfide

Dibenzyl sulfide is a symmetrical thioether. It contains two C6H5CH2- (benzyl) groups linked by a sulfide bridge. It is a colorless or white solid that is soluble in nonpolar solvents.

Dibenzyl sulfide
Names
IUPAC name
Benzylsulfanylmethylbenzene
Other names
1,1'-[Thiobis(methylene)]dibenzene; Benzyl thioether; dibenzyl sulfide
Identifiers
3D model (JSmol)
1911157
ChEMBL
ChemSpider
ECHA InfoCard 100.007.913
EC Number
  • 208-703-6
UNII
UN number 3335
Properties
C14H14S
Molar mass 214.33 g·mol−1
Melting point 49.5 °C (121.1 °F; 322.6 K)
Boiling point 322 °C (612 °F; 595 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Crystallography

The crystal structure of the solid is of the orthorhombic system with space group Pbcn; number 60. The unit cell dimensions are a=13.991 Å b=11.3985 Å c 7.2081 Å. The molecules in the gas take the same form as in the solid with a C2 symmetry.[1]

Production

Benzyl sulfide is commercially manufactured by treating potassium sulfide with benzyl chloride, followed by distillation of the product.[2] It is also obtainable by desulfurization of dibenzyldisulfide with phosphine reagents.[3]

References
  1. Hansson, Christian (19 May 2006). "Dibenzyl sulfide at 150 K". Acta Crystallographica Section E. 62 (6): o2377–o2379. doi:10.1107/S1600536806017491.
  2. Lewis, R.J. Sr, ed. (1993). Hawley's Condensed Chemical Dictionary (12 ed.). New York, NY: Van Nostrand Rheinhold Co. p. 137.
  3. Harpp, David N.; Smith, Roger A. (1978). "Sulfide Synthesis: Benzyl Sulfide". Org. Synth. 58: 138. doi:10.15227/orgsyn.058.0138.
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