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| Names | |||
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IUPAC name
Carbonothioyl dichloride
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| Other names
Thiophosgene; Thiocarbonyl chloride; Carbonothioic dichloride
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| Identifiers | |||
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3D model (JSmol)
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| ChEBI | |||
| ChemSpider | |||
| ECHA InfoCard | 100.006.675 | ||
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PubChem CID
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| RTECS number | XN2450000 | ||
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| 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 |
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| -50.6·10−6 cm3/mol | |||
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Refractive index (nD)
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1.558 | ||
| Structure | |||
| planar, sp2, C2v | |||
| Hazards | |||
| Main hazards | Highly toxic | ||
| Flash point | 62 °C (144 °F; 335 K) | ||
| Related compounds | |||
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Related compounds
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Phosgene Thiocarbonyl fluoride Thiocarbonyl bromide Sulfur dichloride thionyl chloride |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| 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.