> SOCl₂

Thiophosgene
General
Systematic name	Thiophosgene
Other names	Thiocarbonylchloride
Molecular formula	CSCl2
SMILES	?
Molar mass	114.98 g/mol
Appearance	yellow liquid
CAS number	*
Properties
Density and phase	1.50 g/cm3
Solubility in water	decomp.
Other solvents	polar organic solvents rxn with amines, ROH
Melting point	? °C (? K)
Boiling point	70-75 °C (? K)
Viscosity	? cP at ? °C
Structure
Molecular shape	planar, sp2, C2v
Dipole moment	? D
Hazards
MSDS	External MSDS
Main hazards	highly toxic
NFPA 704
R/S statement	R: 22-23-36/37/38 S: 7-9-36/37-45
RTECS number	XN2450000
Supplementary data page
Structure and properties	n, 1.548
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Related compounds
Related compounds	COCl2 SCl2
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Chemical infobox

Thiophosgene is a yellow liquid with the formula CSCl₂. This compound has a trigonal planar geometry. It possesses two reactive C-Cl bonds that allow this reagent to be used in diverse procedures related to organic synthesis.

Synthesis of CSCl₂

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CSCl₂ is prepared in a two-step process from CS₂. In the first step, CS₂ is chlorinated to give trichloromethanesulfenylchloride, CCl₃SCl:

CS₂ + 3 Cl₂ → CCl₃SCl + S₂Cl₂

The chlorination must be controlled as excess chlorine converts CCl₃SCl into CCl₄. Steam distillation separates the CCl₃SCl, a rare sulfenyl chloride, and hydrolyzes the S₂Cl₂. Reduction of CCl₃SCl produces thiophosgene:

CCl₃SCl + M → CSCl₂ + MCl₂

Typically, tin is used for the reducing agent M.

Uses of CSCl₂

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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

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CSCl₂ is considered highly toxic.

References

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• Dyson, G. M. "Thiophosgene" Organic Syntheses, Coll. Vol. 1, p.506; Vol. 6, p.86.
• Holleman, A. F.; Wiberg, E. "Inorganic Chemistry" Academic Press: San Diego, 2001. ISBN 0-12-352651-5.
• Sharma, S. "Thiophosgene in Organic Synthesis" Synthesis, 1978, pages 804-820.

External links

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Inorganic carbon compounds | Sulfides

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