Triphosgene

Triphosgene
Names


IUPAC name Bis(trichloromethyl) carbonate
Other names BTC
Identifiers
CAS Number	32315-10-9^N
3D model (Jmol)	Interactive image
ChemSpider	85216^Y
ECHA InfoCard	100.046.336
PubChem	94429
InChI InChI=1S/C3Cl6O3/c4-2(5,6)11-1(10)12-3(7,8)9^Y Key: UCPYLLCMEDAXFR-UHFFFAOYSA-N^Y InChI=1/C3Cl6O3/c4-2(5,6)11-1(10)12-3(7,8)9 Key: UCPYLLCMEDAXFR-UHFFFAOYAA
SMILES ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl
Properties
Chemical formula	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)
Solubility in water	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 is ^YN ?)
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

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

Triphosgene is used as a reagent in organic synthesis and is a less hazardous substitute for phosgene 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

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]

References

1 2 3 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.
↑ Dr. Heiner Eckert (2011). "Phosgenation Reactions with Phosgene from Triphosgene". Chim. Oggi Chem. Today. 29 (6): 40–46.
↑ Suresh B. Damle (1993-02-08). "Safe handling of diphosgene, triphosgene". C&E News. 71 (6): 4.

External links

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