|Jmol-3D images||Image 1|
|Molar mass||114.98 g/mol|
|Solubility in water||Decomposition|
|Solubility in other solvents||polar organic solvents
rxn with amines and alcohols
|Refractive index (nD)||1.558|
|Molecular shape||planar, sp2, C2v|
|EU Index||Not listed|
|Main hazards||Highly toxic|
|Flash point||62 °C|
| (what is: / ?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Thiophosgene is a red liquid with the formula CSCl2. It is a molecule with trigonal planar geometry. There are two reactive C–Cl bonds that allow it to be used in diverse organic syntheses.
Synthesis 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 + S2Cl2
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:
- CCl3SCl + M → CSCl2 + MCl2
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. Thiophosgene is also known as the appropriate reagent in Corey-Winter synthesis for stereospecific conversion of 1,2-diols into olefins.
CSCl2 is considered highly toxic.