Triphosgene

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Triphosgene
Triphosgene-skeletal.png
Triphosgene-3D-vdW.png
Names
IUPAC name
Bis(trichloromethyl) carbonate
Other names
BTC
Identifiers
32315-10-9 N
ChemSpider 85216 YesY
Jmol-3D images Image
PubChem 94429
Properties
C3Cl6O3
Molar mass 296.748 g/mol
Appearance white crystals
Density 1.780 g/cm3
Melting point 80 °C (176 °F; 353 K)
Boiling point 206 °C (403 °F; 479 K)
Reacts
Hazards
Safety data sheet Fisher MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N verify (what isYesY/N?)
Infobox references

Triphosgene (bis(trichloromethyl) carbonate (BTC), 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.[1] Triphosgene crystals decompose above 200 °C[2]

Preparation[edit]

This compound is commercially available. It is prepared by exhaustive free radical chlorination of dimethyl carbonate:[1]

CH3OCO2CH3 + 6 Cl2 → CCl3OCO2CCl3 + 6 HCl

Triphosgene can be easily recrystallized from boiling hexanes to yield pure white crystals.

Uses[edit]

Triphosgene is used as a reagent in organic synthesis for a variety of chemical transformations including to bond one carbonyl group to two alcohols, and to convert an amine group into isocyanate.[1]

Safety[edit]

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.[3]

See also[edit]

References[edit]

  1. ^ a b c Dr. Heiner Eckert; Dr. Barbara Forster (1987). "Triphosgene, a Crystalline Phosgene Substitute". Angew. Chem. Int. Ed. Engl. 26 (9): 894–895. doi:10.1002/anie.198708941. 
  2. ^ Dr. Heiner Eckert (2011). "Phosgenation Reactions with Phosgene from Triphosgene". Chim. Oggi Chem. Today 29 (6): 40–46. 
  3. ^ Suresh B. Damle (1993-02-08). "Safe handling of diphosgene, triphosgene". C&E News 71 (6): 4. 

External links[edit]