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15217

Sigma-Aldrich

Bis(trichloromethyl) carbonate

purum, ≥99.0% (AT)

Synonym(s):

Triphosgene, tri-Phosgene

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10 G
$121.00
50 G
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About This Item

Linear Formula:
Cl3COCOOCCl3
CAS Number:
32315-10-9
Molecular Weight:
296.75
Beilstein/REAXYS Number:
1787583
EC Number:
250-986-3
MDL number:
MFCD00062848
UNSPSC Code:
12352100
PubChem Substance ID:
57647342
NACRES:
NA.22

$121.00

Available to ship onApril 22, 2025Details

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grade

purum

Quality Level

200

assay

≥99.0% (AT)

form

solid

mp

77-82 °C

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

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application

Bis(trichloromethyl) carbonate was used in the preparation of Fmoc-amino acid chlorides[1]. It was also used in the preparation of aryl-(Z)-vinyl chlorides[2].

Other Notes

Crystalline, easy-to-handle substitute for phosgene; 1 mole of the reagent corresponds in its reactivity to 3 moles phosgene[3][4][5][6]

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_germany

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
BCCN0277
BCCM8869
BCCL7003
BCCL3168
BCCL8636

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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)
P.R.M. Muller
Spec. Chem., 14, 357-357 (1994)
H. Eckert, B. Forster
Angewandte Chemie (International Edition in English), 99, 922-922 (1987)
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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