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32315-10-9 - Triphosgene, 98% - Bis(trichloromethyl) carbonate - BTC - A14932 - Alfa Aesar

A14932 Triphosgene, 98%

CAS Number
Bis(trichloromethyl) carbonate

Size Price ($) Quantity Availability
5g 45.09
25g 135.96
100g 319.20
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Triphosgene, 98%


Chemical Properties

Formula Weight
Melting point
Boiling Point
Moisture Sensitive
Soluble in ether, ethanol, tetrahydrofuran, benzene, cyclohexane, chloroform, hexane, carbon tetrachloride, dichloromethane and chlorobenzene. Insoluble in water.


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.


Moisture sensitive. Store in a cool place. Incompatible with oxidizing agents.

Literature 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, 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.

GHS Hazard and Precautionary Statements

Hazard Statements: H330-H314-H318

Fatal if inhaled. Causes severe skin burns and eye damage. Causes serious eye damage.

Precautionary Statements: P260-P284-P280-P303+P361+P353-P304+P340-P305+P351+P338-P320-P301+P330+P331-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Wear respiratory protection. Wear protective gloves/protective clothing/eye protection/face protection. 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. Specific treatment is urgent (see label). IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Hazard Class
Packing Group
Harmonized Tariff Code


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  • A14433

    Ethyl nitroacetate, 97%
  • A17444

    Trichloromethyl chloroformate, 98%

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