Triphosgene
Encyclopedia
Triphosgene 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.
Phosgene
Phosgene is the chemical compound with the formula COCl2. This colorless gas gained infamy as a chemical weapon during World War I. It is also a valued industrial reagent and building block in synthesis of pharmaceuticals and other organic compounds. In low concentrations, its odor resembles...
, 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
Dimethyl carbonate
Dimethyl carbonate, often abbreviated DMC, a carbonate ester, is a flammable clear liquid boiling at 90 °C. This compound has found use as a methylating agent and more recently as a VOC exempt solvent in paints and adhesives . There is also interest in using this compound as a fuel oxygenate...
.
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.
External links
- Technical datasheet from Aldrich
- Safe handling of diphosgene, triphosgene, Chemical & Engineering News (8 Feb 1993) Vol. 71, No. 6, pp. 4.