Triphosgene, 98%

Name: Triphosgene, 98%
SKU: A14932.06
Price: 74.30 USD

CAS: 32315-10-9 | C3Cl6O3 | 296.73 g/mol

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Catalog number A14932.06

also known as A14932-06

Price (USD)

74.30

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Quantity:

5 g

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Price (USD)

74.30

Each

Chemical Identifiers

CAS32315-10-9

IUPAC Nameditrichloromethyl carbonate

Molecular FormulaC3Cl6O3

InChI KeyUCPYLLCMEDAXFR-UHFFFAOYSA-N

SMILESClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl

Specifications

Specification Sheet

Appearance (Color)Colorless to white to pale cream to pale yellow

Assay (Titration ex Chloride)≥97.5 to ≤102.5%

FormCrystals or powder or crystalline powder or lumps or fused solid

Identification (FTIR)Conforms

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.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
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.

Solubility
Soluble in ether, ethanol, tetrahydrofuran, benzene, cyclohexane, chloroform, hexane, carbon tetrachloride, dichloromethane and chlorobenzene. Insoluble in water.

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

RUO – Research Use Only

General 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.