Thiophosgene; Thiocarbonyl chloride; Carbonothioic dichloride
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||114.98 g/mol|
|Odor||Persistent, choking odor|
|Boiling point||70 to 75 °C (158 to 167 °F; 343 to 348 K)|
|Solubility in other solvents||polar organic solvents|
rxn with amines and alcohols
Refractive index (nD)
|planar, sp2, C2v|
|Main hazards||Highly toxic|
|Flash point||62 °C (144 °F; 335 K)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
The 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:
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. Thiophosgene is also known as the appropriate reagent in Corey-Winter synthesis for stereospecific conversion of 1,2-diols into olefins.
It forms a head-to-tail dimer upon irradiation with UV light:
Unlike thiophosgene monomer, a red liquid, the photodimer, an example of a 1,3-dithietane, is a colorless solid.