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Merck

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:
32315-10-9
Molecular Weight:
296.75
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
57647342
EC Number:
250-986-3
Beilstein/REAXYS Number:
1787583
MDL number:
MFCD00062848
Assay:
≥99.0% (AT)
Form:
solid

Key Documents

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InChI key

UCPYLLCMEDAXFR-UHFFFAOYSA-N

InChI

1S/C3Cl6O3/c4-2(5,6)11-1(10)12-3(7,8)9

SMILES string

ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl

grade

purum

assay

≥99.0% (AT)

form

solid

mp

77-82 °C

functional group

carbonate, chloro

storage temp.

2-8°C

Quality Level

200

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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
GHS06,GHS05

signalword

Danger

hcodes

H314,H330

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCF7338
BCCF6546
BCCF1433
BCCD2152
BCCB4881

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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)
G.B. Gill et al.
Tetrahedron Letters, 30, 3229-3229 (1989)
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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