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Triphosgene is used as a carbonylating agent for aza-peptide synthesis. It reacts with several alfa-amino acids to give the corresponding N-carboxyanhydrides. It is involved in the preparation of the esterification coupling reagent, di-2-thienyl carbonate from 2(5H)-thiophenone. Further, it is used as a reagent in organic synthesis and converts an amino group into isocyanate. In addition to this, it is employed in the preparation of 2-chloronicotinaldehydes through cyclization of the corresponding enamides. It is considered as a useful substitute for phosgene.
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, A1812 .
Menguy, L.; Drouillat, B.; Couty, F. Reaction of N-alkyl azetidines with triphosgene. Tetrahedron Lett. 2015, 56 (47), 6625-6628.
Saputra, M. A.; Ngo, L.; Kartika, R. Synthesis of Vinyl Chlorides via Triphosgene-Pyridine Activation of Ketones. J. Org. Chem. 2015, 80 (17), 8815-8820.
Hazard Statements: H314-H330-H335
Causes severe skin burns and eye damage. Fatal if inhaled. May cause respiratory irritation.
Precautionary Statements: P260-P264b-P271-P280-P284-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P501c
Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. Wear respiratory protection. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant