Triphosgene

• Catalog No.: A14932
• CAS Number: 32315-10-9
• M. F.: C3Cl6O3
• M. W.: 296.7483
• Purity: 98%

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 Hazard statements: H330-H314-H318
• European Hazard Symbols: 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: 是
• Hazard Class: 6.1
• UN Number: UN2928
• Packing Group: II

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.