15217
Bis(trichloromethyl) carbonate
purum, ≥99.0% (AT)
Synonym(s):
Triphosgene, tri-Phosgene
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About This Item
Linear Formula:
Cl3COCOOCCl3
CAS Number:
Molecular Weight:
296.75
Beilstein:
1787583
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
grade
purum
Quality Level
Assay
≥99.0% (AT)
form
solid
mp
77-82 °C
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
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Application
Bis(trichloromethyl) carbonate was used in the preparation of Fmoc-amino acid chlorides. It was also used in the preparation of aryl-(Z)-vinyl chlorides.
Other Notes
Crystalline, easy-to-handle substitute for phosgene; 1 mole of the reagent corresponds in its reactivity to 3 moles phosgene
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 1 Inhalation - Skin Corr. 1B
WGK
WGK 2
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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G.B. Gill et al.
Tetrahedron Letters, 30, 3229-3229 (1989)
H. Eckert, B. Forster
Angewandte Chemie (International Edition in English), 99, 922-922 (1987)
P.R.M. Muller
Spec. Chem., 14, 357-357 (1994)
R. Cortez et al.
Synthetic Communications, 21, 285-285 (1991)
R M Cicchillo et al.
Carbohydrate research, 328(3), 431-434 (2000-11-10)
Treating partially protected sugar hemiacetals with triphosgene in THF results in the formation of glycosyl chlorides. The method is compatible with acid-sensitive isopropylidene protecting groups in the hemiacetal substrates.
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