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| Names | |||
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| IUPAC name Carbonothioyl dichloride | |||
| Other names Thiophosgene; Thiocarbonyl chloride; Carbonothioic dichloride | |||
| Identifiers | |||
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3D model (JSmol) | |||
| ChEBI | |||
| ChemSpider |
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| ECHA InfoCard | 100.006.675 | ||
| RTECS number |
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| UNII | |||
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| Properties | |||
| CSCl2 | |||
| Molar mass | 114.97 g·mol−1 | ||
| Appearance | Red liquid | ||
| Odor | Persistent, choking odor | ||
| Density | 1.50 g/cm3 | ||
| Boiling point | 70 to 75 °C (158 to 167 °F; 343 to 348 K) | ||
| Decomposes | |||
| Solubility in other solvents | Reacts with amines and alcohols, soluble in polar organic solvents | ||
| −50.6·10−6 cm3/mol | |||
Refractive index (nD) | 1.558 | ||
| Structure | |||
| planar, sp2, C2v | |||
| Hazards | |||
| Occupational safety and health (OHS/OSH): | |||
Main hazards | Highly toxic | ||
| Flash point | 62 °C (144 °F; 335 K) | ||
| Related compounds | |||
Related compounds | |||
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
Thiophosgene is a red liquid with the formulaCSCl2. It is a molecule with trigonal planar geometry. There are two reactive C–Cl bonds that allow it to be used in diverseorganic syntheses.[1]
Typically,CSCl2 is prepared in a two-step process fromcarbon disulfide. In the first step, carbon disulfide ischlorinated to givetrichloromethanesulfenyl chloride (CCl3SCl), a raresulfenyl chloride:
The chlorination must be controlled as excess chlorine converts trichloromethanesulfenyl chloride intocarbon tetrachloride. Steam distillation separates the trichloromethanesulfenyl chloride and hydrolyzes the disulfur dichloride. Reduction of trichloromethanesulfenyl chloride with, e.g.,tin[2] ordihydroanthracene[3] produces thiophosgene:
An alternative one-step reaction is[4]
CSCl2 is mainly used to prepare compounds with the connectivityCSX2 where X = OR,NHR.[5] Such reactions proceed via intermediate such as CSClX. Under certain conditions, one can convert primary amines intoisothiocyanates.CSCl2 also serves as adienophile to give, after reduction 5-thiacyclohexene derivatives. Thiophosgene is also known as the appropriate reagent inCorey-Winter synthesis for stereospecific conversion of 1,2-diols intoalkenes.[6]
It forms a head-to-tail dimer upon irradiation with UV light:
Unlike thiophosgene monomer, a red liquid, the photodimer, an example of a 1,3-dithietane, is a colourless solid.[7]Swarts fluorination of the dimer and then cracking is the principal route tothiocarbonyl fluoride.[8]
Thiophosgene decomposes at 200 °C or above to form carbon disulfide and carbon tetrachloride.[9] It has also been observed decomposing tohydrogen sulfide,hydrogen chloride, andcarbonyl sulfide gases via contact withhuman tissue.[10][failed verification]
CSCl2 is considered highly toxic. Inhalation of the substance can cause irritation ofrespiratory system, burns, delayedpulmonary edema anddeath.[11]
| Authority control databases: National |
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