330752
Triphosgene
reagent grade, 98%
Synonym(s):
Bis(trichloromethyl) carbonate
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About This Item
Linear Formula:
Cl3COCOOCCl3
CAS Number:
Molecular Weight:
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
grade
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
Storage Class
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
Regulatory Information
危险化学品
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Related Content
A simple one-pot method for the preparation of allyl azides from allyl alcohols using triphosgene: Synthesis of N1-cinnamyl azetidin-2-ones
Jayanthi A, et al.
Synlett, 6, 979-982 (2004)
Convenient route to thiocarbonates from alcohols, thiols, and triphosgene
Movassagh B and Soleiman-Beigi M
Synthetic Communications, 40(23), 3467-3471 (2010)
Coordination of chiral amines to coordinatively unsaturated Cp* Ir-amino acid complexes allows determination of enantiomeric purity
Grotjahn DB and Joubran C
Tetrahedron Asymmetry, 6, 745-745 (1995)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 330752-5G | 04061826726242 |
| 330752-100G | 04061826726211 |
| 330752-500G | 04061826726235 |
| 330752-25G | 04061826726228 |