|Preferred IUPAC name
3D model (JSmol)
|Molar mass||296.748 g/mol|
|Melting point||80 °C (176 °F; 353 K)|
|Boiling point||206 °C (403 °F; 479 K)|
|Solubility||*soluble in dichloromethane|
|Safety data sheet||SDS Triphosgene|
|GHS signal word||Danger|
|P260, P280, P284, P305+351+338, P310|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
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. Triphosgene crystals decompose above 200 °C.
- CH3OCO2CH3 + 6 Cl2 → CCl3OCO2CCl3 + 6 HCl
Triphosgene can be easily recrystallized from boiling hexanes to yield pure white crystals.
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.
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.
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- "Immobilization and chiral recognition of 3,5-dimethylphenylcarbamates of cellulose and amylose bearing 4-(trimethoxysilyl)phenylcarbamate groups". Chirality. doi:10.1002/chir.20722.
- Zhou, Yuhan; Gong, Runjun; Miao, Weirong (2006-09-01). "New Method of Synthesizing N‐Alkoxycarbonyl‐N‐arylamide with Triphosgene". Synthetic Communications. 36 (18): 2661–2666. doi:10.1080/00397910600764675. ISSN 0039-7911.
- Sigma-Aldrich Co., Triphosgene. Retrieved on 2018-06-12.
- 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". Chemical & Engineering News. 71 (6): 4.