Thiophosgene
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| Thiophosgene | ||
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| 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 |
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| 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 |
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| R/S statement | R: 22-23-36/37/38 S: 7-9-36/37-45 |
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| RTECS number | XN2450000 | |
| Supplementary data page | ||
| Structure and properties |
n, 1.548 | |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
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| Spectral data | UV, IR, NMR, MS | |
| Related compounds | ||
| Related compounds | COCl2 SCl2 |
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| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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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.
Contents |
[edit] Synthesis of CSCl2
CSCl2 is prepared in a two-step process from CS2. In the first step, CS2 is chlorinated to give trichloromethanesulfenylchloride, CCl3SCl:
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- 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:
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- CCl3SCl + M → CSCl2 + MCl2
Typically, tin is used for the reducing agent M.
[edit] 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.
[edit] Safety considerations
CSCl2 is considered highly toxic.
[edit] 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.
