| Triphosgene | |
|---|---|
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Bis(trichloromethyl) carbonate |
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| Identifiers | |
| PubChem | 94429 |
| ChemSpider | 85216 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C3Cl6O3 |
| Molar mass | 296.748 g/mol |
| Melting point |
80 °C, 353 K, 176 °F |
| Boiling point |
206 °C, 479 K, 403 °F |
| Solubility in water | Reacts |
| Hazards | |
| MSDS | Fisher MSDS |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Triphosgene (Bis(trichloromethyl) carbonate, C3Cl6O3) is a chemical compound that is used as a safer substitute for phosgene, because at room temperature it is a solid crystal, as opposed to phosgene which is a gas. Triphosgene crystals decompose at around 130 °C, although, the decomposition temperature of impure samples can be much lower. Triphosgene is used in organic synthesis to bond one carbonyl group to two alcohols, as in the synthesis of octalactin B. It is prepared by exhaustive chlorination of dimethyl carbonate.
Triphosgene can be easily recrystallized from boiling hexanes to yield pure white crystals. The toxicity of triphosgene is the same as phosgene since it decomposes to phosgene on heating and upon reaction with nucleophiles. Even trace moisture leads to formation of phosgene. Therefore this reagent can be safely handled if one takes all the precautions as for phosgene. Anything less may result in a dangerous situation.