Dibenzyl sulfide

Dibenzyl sulfide
Names
	Preferred IUPAC name 1,1′-[Sulfanediylbis(methylene)]dibenzene
	Other names 1,1′-[Thiobis(methylene)]dibenzene; Benzyl thioether; dibenzyl sulfide
Identifiers
CAS Number	538-74-9;
3D model (JSmol)	Interactive image;
Beilstein Reference	1911157
ChEMBL	ChEMBL1369381;
ChemSpider	10407;
ECHA InfoCard	100.007.913
EC Number	208-703-6;
PubChem CID	10867;
UNII	Q08048624M;
UN number	3335
CompTox Dashboard (EPA)	DTXSID6024599;
	InChI InChI=1S/C14H14S/c1-3-7-13(8-4-1)11-15-12-14-9-5-2-6-10-14/h1-10H,11-12H2 Key: LUFPJJNWMYZRQE-UHFFFAOYSA-N;
	SMILES C1=CC=C(C=C1)CSCC2=CC=CC=C2;
Properties
Chemical formula	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

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.^[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

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

[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.