330752

Triphosgene

reagent grade, 98%

• Synonym(s): Bis(trichloromethyl) carbonate
• 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

Properties

• 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
• 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

Description

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.

Safety Information

• Pictograms: GHS06,GHS05
• Signal Word: Danger
• Hazard Statements: H314,H330
• Precautionary Statements: P260 - P271 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• 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