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330752

Sigma-Aldrich

Triphosgene

reagent grade, 98%

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Synonym(s):
Bis(trichloromethyl) carbonate
Linear Formula:
Cl3COCOOCCl3
CAS Number:
Molecular Weight:
296.75
Beilstein:
1787583
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

grade

reagent grade

Quality Level

Assay

98%

form

powder

reaction suitability

reaction type: Coupling Reactions

bp

203-206 °C (lit.)

mp

79-83 °C (lit.)

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
P52652539899281883
Triphosgene reagent grade, 98%

Sigma-Aldrich

330752

Triphosgene

Propylene carbonate ReagentPlus®, 99%

Sigma-Aldrich

P52652

Propylene carbonate

form

powder

form

liquid

form

-

form

-

reaction suitability

reaction type: Coupling Reactions

reaction suitability

-

reaction suitability

reaction type: Carbonylations

reaction suitability

-

bp

203-206 °C (lit.)

bp

240 °C (lit.)

bp

-

bp

-

mp

79-83 °C (lit.)

mp

−55 °C (lit.)

mp

47-50 °C (lit.)

mp

140-142 °C (lit.)

storage temp.

2-8°C

storage temp.

-

storage temp.

-

storage temp.

-

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.

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.

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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Triphosgene, a crystalline phosgene substitute
Eckert, Heiner and Forster, Barbara
Angewandte Chemie (International Edition in English), 26(9), 894-895 (1987)
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 versatile reagent for the synthesis of azetidin-2-ones
Krishnaswamy D, et al.
Tetrahedron, 58(11), 2215-2225 (2002)
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)
Coordination of chiral amines to coordinatively unsaturated Cp* Ir-amino acid complexes allows determination of enantiomeric purity
Grotjahn DB and Joubran C
Tetrahedron Asymmetry, 6, 745-745 (1995)

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