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Thiophosgene

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Thiophosgene
Thiophosgene
Thiophosgene
Thiophosgene
Thiophosgene
Names
IUPAC name Carbonothioyl dichloride
Other names Thiophosgene; Thiocarbonyl chloride; Carbonothioic dichloride
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.006.675 Edit this at Wikidata
PubChem CID
RTECS number
  • XN2450000
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/CCl2S/c2-1(3)4Key: ZWZVWGITAAIFPS-UHFFFAOYSA-N
  • InChI=1/CCl2S/c2-1(3)4Key: ZWZVWGITAAIFPS-UHFFFAOYAH
SMILES
  • ClC(Cl)=S
Properties
Chemical formula CSCl2
Molar mass 114.98 g/mol
Appearance Red liquid
Density 1.50 g/cm
Boiling point 70–75 °C
Solubility in water Decomp.
Solubility in other solvents polar organic solvents
rxn with amines and alcohols
Refractive index (nD) 1.548
Structure
Molecular shape planar, sp, C2v
Hazards
Occupational safety and health (OHS/OSH):
Main hazards Highly toxic
Flash point 62 °C
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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

Typically, 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. Thiophosgene is also known as the appropriate reagent in Corey-Winter synthesis for stereospecific converting 1,2-diols into olefins.

Safety considerations

CSCl2 is considered highly toxic.

References

This article has an unclear citation style. The references used may be made clearer with a different or consistent style of citation and footnoting. (September 2007) (Learn how and when to remove this message)
  • Dyson, G. M. "Thiophosgene" Organic Syntheses, Coll. Vol. 1, p. 506; Vol. 6, p. 86.
  • Holleman, Arnold Frederik; Wiberg, Egon (2001), Wiberg, Nils (ed.), Inorganic Chemistry, translated by Eagleson, Mary; Brewer, William, San Diego/Berlin: Academic Press/De Gruyter, ISBN 0-12-352651-5
  • Sharma, S. "Thiophosgene in Organic Synthesis" Synthesis, 1978, pages 804-820.
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