330752
Triphosgene
reagent grade, 98%
Sinónimos:
Bis(trichloromethyl) carbonate
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Fórmula lineal:
Cl3COCOOCCl3
Número CAS:
Peso molecular:
296.75
UNSPSC Code:
12352108
NACRES:
NA.22
PubChem Substance ID:
EC Number:
250-986-3
Beilstein/REAXYS Number:
1787583
MDL number:
Assay:
98%
Form:
powder
Servicio técnico
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reagent grade
Quality Level
assay
98%
form
powder
reaction suitability
reaction type: Coupling Reactions
bp
203-206 °C (lit.)
mp
79-83 °C (lit.)
functional group
carbonate, chloro
storage temp.
2-8°C
SMILES string
ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl
InChI
1S/C3Cl6O3/c4-2(5,6)11-1(10)12-3(7,8)9
InChI key
UCPYLLCMEDAXFR-UHFFFAOYSA-N
General description
Triphosgene [Bis(trichloromethyl)carbonate] is a versatile organic reagent used in organic synthesis alternative to phosgene. A catalytic amount of triphosgene is particularly used in chloroformylations, carbonylations, chlorinations, and dehydration reactions.
It is also commonly employed as a coupling agent in the synthesis of carbonyl compounds.
It is also commonly employed as a coupling agent in the synthesis of carbonyl compounds.
Application
Triphosgene can be employed as a reagent to prepare:
- Thiocarbonates from thiols and alcohols by one-pot, three-component reaction.
- Substituted azetidin-2-ones from acids and imines via ketene–imine cycloaddition reaction.
- Methyl (S)-2-isocyanato-3-phenylpropanoate from L-phenylalanine methyl ester hydrochloride in the presence of sodium bicarbonate.
- Acyl azides derivatives from various carboxylic acids and sodium azide.
- Immunosuppressant agent cyclosporin by solid-phase peptide synthesis.
- Allyl azides from allyl alcohols and sodium azide in one pot method.
- Esterification coupling reagent di-2-thienyl carbonate, from 2(5H)-thiophenone.
- 2-Chloronicotinaldehydes via cyclization of the corresponding enamides.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 1 Inhalation - Skin Corr. 1B
Clase de almacenamiento
6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
wgk
WGK 2
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
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Contenido relacionado
Triphosgene: a versatile reagent for the synthesis of azetidin-2-ones
Krishnaswamy D, et al.
Tetrahedron, 58(11), 2215-2225 (2002)
A mild and efficient method for the preparation of acyl azides from carboxylic acids using triphosgene
Gumaste VK, et al.
Tetrahedron Letters, 43(7), 1345-1346 (2002)
Tetrahedron, 62, 8398-8398 (2006)