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Triphosgene

Catalog No. A14932 Name Alfa Aesar
CAS Number 32315-10-9 Website
M. F. C3Cl6O3 Telephone
M. W. 296.7483 Fax
Purity 98% Email
Storage Chembase ID: 88396

SYNONYMS

Title
三光气
IUPAC name
ditrichloromethyl carbonate
IUPAC Traditional name
triphosgene
Synonyms
Bis(trichloromethyl) carbonate
BTC

DATABASE IDS

EC Number 250-986-3
CAS Number 32315-10-9
MDL Number MFCD00062848
Beilstein Number 1787583

PROPERTIES

Purity 98%
Boiling Point 203-206°C
Density 1.600
Melting Point 77-91°C
GHS Pictograms GHS05
GHS Pictograms GHS06
GHS Hazard statements H330-H314-H318
European Hazard Symbols Toxic Toxic (T)
GHS Precautionary statements P260-P303+P361+P353-P304+P340-P305+P351+P338-P320-P405-P501A
Risk Statements 23-29-34
Safety Statements 4-7/8-9-20-26-36/37/39-45
Storage Warning Moisture Sensitive
TSCA Listed
Hazard Class 6.1
UN Number UN2928
Packing Group II

DETAILS

REFERENCES

  • Convenient crystalline alternative to phosgene in many reactions. See also Trichloromethyl chloroformate, A17444. Possible applications include conversion of amines to isocyanates, diols to carbonates, acids to acyl halides, etc.: Angew. Chem. Int. Ed., 26, 894 (1987). For a brief review, see: J. Prakt. Chem./ Chem. Ztg., 337, 516 (1995); for a comprehensive review: Synthesis, 553 (1996).
  • In combination with triphenylphosphine, is a mild reagent for the conversions of alcohols to alkyl chlorides: Synth. Commun., 23, 711 (1993), epoxides to vicinal dichlorides: Synth. Commun., 24, 1715 (1994), and acids to acyl chlorides: Tetrahedron Lett., 38, 6489 (1997).
  • Trap for titanocycle intermediates in the bicyclization of enynes using the titanocene dichloride (Bis(cyclopentadienyl)titanium dichloride, A11456) - Mg metal system: J. Org. Chem., 63, 9285 (1998):
  • In combination with triethylamine, dehydrates formamides to isocyanides, and carboxylic acids to their anhydrides: J. Org. Chem., 58, 1646 (1993); 59, 2913 (1994).
  • In combination with Dimethyl sulfoxide, A13280, has been used for the low-temperature Swern-type oxidation of alcohols to aldehydes: J. Org. Chem., 56, 5948 (1991); 58, 1646 (1993); Org. Prep. Proced. Int., 24, 363 (1992). Compare Oxalyl chloride, A18012.