Thiophosgene

Chembox new
Name = Thiophosgene
ImageFile = Thiophosgene-2D.png ImageName = Thiophosgene
ImageFile1 = Thiophosgene-3D-vdW.png ImageName1 = Thiophosgene
IUPACName = Thiophosgene
OtherNames = Thiocarbonylchloride
Section1 = Chembox Identifiers
SMILES =
CASNo = 463-71-8
RTECS = XN2450000
Section2 = Chembox Properties
Formula = CSCl₂
MolarMass = 114.98 g/mol
Appearance = yellow liquid
Density = 1.50 g/cm³
Solubility = decomp.
Solvent = other solvents
SolubleOther = polar organic solvents
rxn with amines, ROH
MeltingPt =
BoilingPt = 70-75 °C
Viscosity =
RefractIndex = 1.548
Section3 = Chembox Structure
MolShape = planar, sp², C_2v
Dipole =
Section7 = Chembox Hazards
ExternalMSDS =
MainHazards = highly toxic
RPhrases = 22-23-36/37/38
SPhrases = 7-9-36/37-45
Section8 = Chembox Related
OtherCpds = COCl₂
SCl₂

SOCl₂

Thiophosgene is a yellow liquid with the formula CSCl₂. This compound has a trigonal planar geometry. It possesses two reactive C-Cl bonds that allow this reagent to be used in diverse procedures related to organic synthesis.

ynthesis of CSCl₂

CSCl₂ is prepared in a two-step process from carbon disulfide. In the first step, carbon disulfide is chlorinated to give trichloromethanesulfenyl chloride, CCl₃SCl:::CS₂ + 3 Cl₂ → CCl₃SCl + S₂Cl₂The chlorination must be controlled as excess chlorine converts trichloromethanesulfenyl chloride into carbon tetrachloride. Steam distillation separates the trichloromethanesulfenyl chloride, a rare sulfenyl chloride, and hydrolyzes the sulfur monochloride. Reduction of trichloromethanesulfenyl chloride produces thiophosgene::: CCl₃SCl + M → CSCl₂ + MCl₂Typically, tin is used for the reducing agent M.

Uses of CSCl₂

CSCl₂ is mainly used to prepare compounds with the connectivity CSX₂ where X = OR, NHR. Such reactions proceed via intermediate such as CSClX. Under certain conditions, one can convert primary amines into isothiocyanates.CSCl₂ also serves as a dienophile to give, after reduction 5-thiacyclohexene derivatives.

afety considerations

CSCl₂ is considered highly toxic.

References

*Dyson, G. M. "Thiophosgene" Organic Syntheses, Coll. Vol. 1, p.506; Vol. 6, p.86.
*Holleman, A. F.; Wiberg, E. "Inorganic Chemistry" Academic Press: San Diego, 2001. ISBN 0-12-352651-5.
*Sharma, S. "Thiophosgene in Organic Synthesis" Synthesis, 1978, pages 804-820.