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Sigma-Aldrich

Bis(trichloromethyl) carbonate

purum, ≥99.0% (AT)

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Synonym(s):
Triphosgene, tri-Phosgene
Linear Formula:
Cl3COCOOCCl3
CAS Number:
Molecular Weight:
296.75
Beilstein:
1787583
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

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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1 of 4

This Item
8.142832326175061
form

solid

form

crystals

form

-

form

lumps

mp

77-82 °C

mp

77-81 °C

mp

-

mp

-

storage temp.

2-8°C

storage temp.

2-30°C

storage temp.

2-8°C

storage temp.

-

Quality Level

200

Quality Level

200

Quality Level

-

Quality Level

-

grade

purum

grade

-

grade

-

grade

-

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

CorrosionSkull and crossbones

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

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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)
E Falb et al.
The journal of peptide research : official journal of the American Peptide Society, 53(5), 507-517 (1999-07-29)
This paper reports procedures for the straightforward in situ generation of Fmoc-amino acid chlorides using bis-(trichloromethyl)carbonate (BTC) and their utilization for difficult couplings during solid-phase peptide synthesis. The BTC-mediated coupling of all Fmoc-protected proteinogenic amino acids to a large variety

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