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A14932 Triphosgene, 98%

Codice CAS
32315-10-9
Sinonimi
Bis(trichloromethyl) carbonate
BTC

Stock No. Dimensioni Prezzo ($) Quantità Disponibilità
A14932-06 5g 52,90
A14932-14 25g 140,00
A14932-22 100g 411,00
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Triphosgene, 98%

MDL
MFCD00062848
EINECS
250-986-3

Proprietà chimiche

Formula
C3Cl6O3
Peso formula
296.75
Punto di fusione
77-91°
Punto di ebollizione
203-206°
Densità
1.600
Storage & Sensitivity
Keep Cold. Moisture Sensitive. Store under Argon.
Solubilità
Soluble in ether, ethanol, tetrahydrofuran, benzene, cyclohexane, chloroform, hexane, carbon tetrachloride, dichloromethane and chlorobenzene. Insoluble in water.

Applicazioni

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.

Note

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

Letteratura

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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H330-H314-H318

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

Dichiarazioni precauzionali: P303+P361+P353-P304+P340-P305+P351+P338-P320-P405-P501a

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). Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Beilstein
1787583
Classe di rischio
6.1
Gruppo di imballaggio
II
Codice tariffe armonizzato
2920.90
TSCA
Yes

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