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Merck
CN

330752

Triphosgene

reagent grade, 98%

Synonym(s):

Bis(trichloromethyl) carbonate

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About This Item

Linear Formula:
Cl3COCOOCCl3
CAS Number:
32315-10-9
Molecular Weight:
296.75
UNSPSC Code:
12352108
NACRES:
NA.22
PubChem Substance ID:
24859885
EC Number:
250-986-3
Beilstein/REAXYS Number:
1787583
MDL number:
MFCD00062848

Key Documents

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Product Name

Triphosgene, reagent grade, 98%

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

reagent grade

assay

98%

form

powder

reaction suitability

reaction type: Coupling Reactions

bp

203-206 °C (lit.)

mp

79-83 °C (lit.)

functional group

carbonate
chloro

storage temp.

2-8°C

Quality Level

200

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Application

Triphosgene can be employed as a reagent to prepare:
  • Thiocarbonates from thiols and alcohols by one-pot, three-component reaction.
  • Substituted azetidin-2-ones from acids and imines via ketene–imine cycloaddition reaction.
  • Methyl (S)-2-isocyanato-3-phenylpropanoate from L-phenylalanine methyl ester hydrochloride in the presence of sodium bicarbonate.
  • Acyl azides derivatives from various carboxylic acids and sodium azide.
  • Immunosuppressant agent cyclosporin by solid-phase peptide synthesis.
  • Allyl azides from allyl alcohols and sodium azide in one pot method.
  • Esterification coupling reagent di-2-thienyl carbonate, from 2(5H)-thiophenone.
  • 2-Chloronicotinaldehydes via cyclization of the corresponding enamides.

General description

Triphosgene [Bis(trichloromethyl)carbonate] is a versatile organic reagent used in organic synthesis alternative to phosgene. A catalytic amount of triphosgene is particularly used in chloroformylations, carbonylations, chlorinations, and dehydration reactions.
It is also commonly employed as a coupling agent in the synthesis of carbonyl compounds.

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

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ9865
MKCW6260
MKCV0717
MKCS8231
BCCF6546

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A mild and efficient method for the preparation of acyl azides from carboxylic acids using triphosgene
Gumaste VK, et al.
Tetrahedron Letters, 43(7), 1345-1346 (2002)
Triphosgene: a versatile reagent for the synthesis of azetidin-2-ones
Krishnaswamy D, et al.
Tetrahedron, 58(11), 2215-2225 (2002)
A Safe and Efficient Method for Preparation of N,N′-Unsymmetrically Disubstituted Ureas Utilizing Triphosgene.
Majer P, et al.
The Journal of Organic Chemistry, 59, 1937-1938 (1994)
Triphosgene, a crystalline phosgene substitute
Eckert, Heiner and Forster, Barbara
Angewandte Chemie (International Edition in English), 26(9), 894-895 (1987)
Synthesis of Amino Acid Ester Isocyanates: Methyl (S)-2-Isocyanato-3-Phenylpropanoate: Benzenepropanoic acid, α-isocyanato-, methyl ester,(S)
Tsai JH, et al.
Organic Syntheses, 78, 220-220 (2003)
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