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330752

Sigma-Aldrich

Triphosgene

reagent grade, 98%

Synonym(s):

Bis(trichloromethyl) carbonate

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About This Item

Linear Formula:
Cl3COCOOCCl3
CAS Number:
Molecular Weight:
296.75
Beilstein:
1787583
EC Number:
MDL number:
UNSPSC Code:
12352108
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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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

Skull and crossbonesCorrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 1 Inhalation - Skin Corr. 1B

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Convenient route to thiocarbonates from alcohols, thiols, and triphosgene
Movassagh B and Soleiman-Beigi M
Synthetic Communications, 40(23), 3467-3471 (2010)
A simple one-pot method for the preparation of allyl azides from allyl alcohols using triphosgene: Synthesis of N1-cinnamyl azetidin-2-ones
Jayanthi A, et al.
Synlett, 6, 979-982 (2004)
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)
Aldrichimica Acta, 21, 47-47 (1988)
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)

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