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Thiocarbonyl chloride

Thiophosgene
Thiophosgene
Thiophosgene
Names
IUPAC name
Carbonothioyl dichloride
Other names
Thiophosgene; Thiocarbonyl chloride; Carbonothioic dichloride
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.006.675
PubChem CID
RTECS number XN2450000
UNII
Properties
CSCl2
Molar mass 114.98 g/mol
Appearance Red liquid
Density 1.50 g/cm3
Boiling point 70 to 75 °C (158 to 167 °F; 343 to 348 K)
Decomposition
Solubility in other solvents polar organic solvents
rxn with amines and alcohols
-50.6·10−6 cm3/mol
1.558
Structure
planar, sp2, C2v
Hazards
Main hazards Highly toxic
Flash point 62 °C (144 °F; 335 K)
Related compounds
Related compounds
Phosgene
Thiocarbonyl fluoride
Thiocarbonyl bromide
Sulfur dichloride
thionyl chloride
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

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.

CSCl2 is prepared in a two-step process from carbon disulfide. In the first step, carbon disulfide is chlorinated to give trichloromethanesulfenyl chloride (perchloromethyl mercaptan), CCl3SCl:

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:

Typically, tin is used for the reducing agent M.

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.


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