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

grade

reagent grade

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
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H314,H330

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

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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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)
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)
Facile and selective synthesis of chloronicotinaldehydes by the Vilsmeier reaction
Gangadasu B, et al.
Tetrahedron, 62(35), 8398-8403 (2006)
Triphosgene as highly efficient reagent for the solid-phase coupling of N-alkylated amino acids?total synthesis of cyclosporin O
Thern B, et al.
Tetrahedron Letters, 43(28), 5013-5016 (2002)
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