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Triphosgene

Triphosgene
Names
Preferred IUPAC name
Bis(trichloromethyl) carbonate
Other names
BTC
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.046.336 Edit this at Wikidata
UNII
  • InChI=1S/C3Cl6O3/c4-2(5,6)11-1(10)12-3(7,8)9 checkY
    Key: UCPYLLCMEDAXFR-UHFFFAOYSA-N checkY
  • InChI=1/C3Cl6O3/c4-2(5,6)11-1(10)12-3(7,8)9
    Key: UCPYLLCMEDAXFR-UHFFFAOYAA
  • ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl
Properties
C3Cl6O3
Molar mass 296.748 g/mol
Appearance white solid
Density 1.780 g/cm3
Melting point 80 °C (176 °F; 353 K)
Boiling point 206 °C (403 °F; 479 K)
Reacts
Solubility *soluble in dichloromethane[1]
  • soluble in THF[2]
  • soluble in toluene[3]
Hazards
GHS labelling:
GHS06: ToxicGHS05: Corrosive[4]
Danger
H314, H330[4]
P260, P280, P284, P305+P351+P338, P310[4]
Safety data sheet (SDS) SDS Triphosgene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Triphosgene (bis(trichloromethyl) carbonate (BTC) is a chemical compound with the formula OC(OCCl3)2. It is used as a solid substitute for phosgene, which is a gas and diphosgene, which is a liquid.[5][6] Triphosgene is stable up to 200 °C.[7] Triphosgene is used in a variety of halogenation reactions.[8]

  1. ^ Ouimet MA, Stebbins ND, Uhrich KE (August 2013). "Biodegradable coumaric acid-based poly(anhydride-ester) synthesis and subsequent controlled release". Macromolecular Rapid Communications. 34 (15): 1231–1236. doi:10.1002/marc.201300323. PMC 3789234. PMID 23836606.
  2. ^ Tang S, Ikai T, Tsuji M, Okamoto Y (January 2010). "Immobilization and chiral recognition of 3,5-dimethylphenylcarbamates of cellulose and amylose bearing 4-(trimethoxysilyl)phenylcarbamate groups". Chirality. 22 (1): 165–172. doi:10.1002/chir.20722. PMID 19455617.
  3. ^ Zhou Y, Gong R, Miao W (September 2006). "New Method of Synthesizing N-Alkoxycarbonyl-N-arylamide with Triphosgene". Synthetic Communications. 36 (18): 2661–2666. doi:10.1080/00397910600764675. S2CID 98578315.
  4. ^ a b c Sigma-Aldrich Co., Triphosgene.
  5. ^ Roestamadji, Juliatiek; Mobashery, Shahriar (2001). "Bis(trichloromethyl) Carbonate". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rb200. ISBN 0471936235.
  6. ^ Heiner Eckert; Barbara Forster (1987). "Triphosgene, a Crystalline Phosgene Substitute". Angew. Chem. Int. Ed. Engl. 26 (9): 894–895. doi:10.1002/anie.198708941.
  7. ^ Cite error: The named reference :0 was invoked but never defined (see the help page).
  8. ^ Cite error: The named reference :2 was invoked but never defined (see the help page).

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