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

A14932 Triphosgene, 98%

Numéro CAS
32315-10-9
Synonymes
Bis(trichloromethyl) carbonate
BTC

Dimensions Prix ($) Quantité Disponibilité
5g 45,09
25g 135,96
100g 319,20
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Triphosgene, 98%

MDL
MFCD00062848
EINECS
250-986-3

Propriétés chimiques

Formule
C3Cl6O3
Poids formulaire
296.75
Point de fusion
77-91°
Point d'ébullition
203-206°
Densité
1.600
Sensibilité
Moisture Sensitive
Solubilité
Soluble in ether, ethanol, tetrahydrofuran, benzene, cyclohexane, chloroform, hexane, carbon tetrachloride, dichloromethane and chlorobenzene. Insoluble in water.

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.

Notes

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

Références bibliographiques

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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H330-H314-H318

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

Mentions de prudence: 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.

Autres références

Beilstein
1787583
Classe de danger
6.1
Groupe d'emballage
II
Code tarifaire harmonisé
2920.90
TSCA
Yes

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Consulté récemment

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Analytique et matériel de laboratoire