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Thiophosgene
Thiophosgene
Thiophosgene
IUPAC name
Other names Thiocarbonyl chloride
Carbonothioic dichloride
Identifiers
CAS number 463-71-8 Yes check.svgY
RTECS number XN2450000
SMILES
Properties
Molecular formula CSCl2
Molar mass 114.98 g/mol
Appearance yellow liquid
Density 1.50 g/cm3
Boiling point

70–75 °C

Solubility in water decomp.
Solubility in other solvents polar organic solvents
rxn with amines, ROH
Refractive index (nD) 1.548
Structure
Molecular shape planar, sp2, C2v
Hazards
EU Index Not listed
Main hazards highly toxic
Related compounds
Related compounds Phosgene
Sulfur dichloride
thionyl chloride
 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Thiophosgene is a yellow liquid with the formula CSCl2. It's a molecule with trigonal planar geometry. There are two reactive C–Cl bonds that allow it to be used in diverse organic syntheses.

Contents

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.

Safety 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. (2001), Inorganic Chemistry, San Diego: Academic Press, ISBN 0-12-352651-5  
  • Sharma, S. "Thiophosgene in Organic Synthesis" Synthesis, 1978, pages 804-820.
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Thiophosgene
Identifiers
CAS number 463-71-8 Y
RTECS number XN2450000
SMILES
Properties
Molecular formula CSCl2
Molar mass 114.98 g/mol
Appearance yellow liquid
Density 1.50 g/cm3
Boiling point

70–75 °C

Solubility in water decomp.
Solubility in other solvents polar organic solvents
rxn with amines, ROH
Refractive index (nD) 1.548
Structure
Molecular shape planar, sp2, C2v
Hazards
EU Index Not listed
Main hazards highly toxic
Related compounds
Related compounds Phosgene
Sulfur dichloride
thionyl chloride
 Y (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Thiophosgene is a yellow 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.

Contents

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.

Safety 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. (2001), [Expression error: Unexpected < operator Inorganic Chemistry], San Diego: Academic Press, ISBN 0-12-352651-5 
  • Sharma, S. "Thiophosgene in Organic Synthesis" Synthesis, 1978, pages 804-820.


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