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Thiophosgene

General

Systematic name

Thiophosgene

Other names

Thiocarbonylchloride

Molecular formula

CSCl₂

SMILES

Molar mass

114.98 g/mol

Appearance

yellow liquid

CAS number

[463-71-8]

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, C_2v

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

COCl₂
SCl₂

SOCl₂

Except where noted otherwise, data are given for
materials in their standard state (at 25 °C, 100 kPa)
Infobox disclaimer and references

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.

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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. "Inorganic Chemistry" Academic Press: San Diego, 2001. ISBN 0-12-352651-5.
Sharma, S. "Thiophosgene in Organic Synthesis" Synthesis, 1978, pages 804-820.

Categories: Inorganic carbon compounds | Sulfides

This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Thiophosgene". A list of authors is available in Wikipedia.