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Key Documents

15217

Sigma-Aldrich

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

grade

purum

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

Pictograms

Skull and crossbonesCorrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 1 Inhalation - Skin Corr. 1B

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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R. Cortez et al.
Synthetic Communications, 21, 285-285 (1991)
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)
Dun Zhang et al.
The Journal of organic chemistry, 71(4), 1750-1753 (2006-02-14)
A method for the preparation of enantiomerically pure hydantoins from optically pure alpha-amino amides utilizing triphosgene is described. We also propose that the racemization observed with 1,1'-carbonyldiimidazole (CDI) for this type of reaction is due to the imidazole carbamate intermediates.

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