Misplaced Pages

Dibenzyl sulfide

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Dibenzyl sulfide
Names
Preferred IUPAC name 1,1′-dibenzene
Other names 1,1′-dibenzene; Benzyl thioether; dibenzyl sulfide
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 1911157
ChEMBL
ChemSpider
ECHA InfoCard 100.007.913 Edit this at Wikidata
EC Number
  • 208-703-6
PubChem CID
UNII
UN number 3335
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C14H14S/c1-3-7-13(8-4-1)11-15-12-14-9-5-2-6-10-14/h1-10H,11-12H2Key: LUFPJJNWMYZRQE-UHFFFAOYSA-N
SMILES
  • C1=CC=C(C=C1)CSCC2=CC=CC=C2
Properties
Chemical formula C14H14S
Molar mass 214.33 g·mol
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 , 100 kPa). Infobox references
Chemical compound

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.

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.

Production

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

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.
Categories: