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Sigma-Aldrich

Triphosgene

Triphosgene

reagent grade, 98%

Sinonimo/i:

Bis(trichloromethyl) carbonate

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5 G
CHF 63.50
25 G
CHF 139.00
100 G
CHF 470.00
500 G
CHF 971.00

About This Item

Formula condensata:
Cl3COCOOCCl3
Numero CAS:
Peso molecolare:
296.75
Beilstein:
1787583
Numero CE:
Numero MDL:
Codice UNSPSC:
12352108
ID PubChem:
NACRES:
NA.22

CHF 63.50


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Grado

reagent grade

Livello qualitativo

Saggio

98%

Stato

powder

Impiego in reazioni chimiche

reaction type: Coupling Reactions

P. ebollizione

203-206 °C (lit.)

Punto di fusione

79-83 °C (lit.)

Gruppo funzionale

carbonate
chloro

Temperatura di conservazione

2-8°C

Stringa SMILE

ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl

InChI

1S/C3Cl6O3/c4-2(5,6)11-1(10)12-3(7,8)9
UCPYLLCMEDAXFR-UHFFFAOYSA-N

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Descrizione generale

Triphosgene [Bis(trichloromethyl)carbonate] is a versatile organic reagent used in organic synthesis alternative to phosgene.[1][2][3] A catalytic amount of triphosgene is particularly used in chloroformylations, carbonylations, chlorinations, and dehydration reactions.[4][5]
It is also commonly employed as a coupling agent in the synthesis of carbonyl compounds.[6][6][7]
[5]

Applicazioni

Triphosgene can be employed as a reagent to prepare:
  • Thiocarbonates from thiols and alcohols by one-pot, three-component reaction.[5]
  • Substituted azetidin-2-ones from acids and imines via ketene–imine cycloaddition reaction.[8]
  • Methyl (S)-2-isocyanato-3-phenylpropanoate from L-phenylalanine methyl ester hydrochloride in the presence of sodium bicarbonate.[9]
  • Acyl azides derivatives from various carboxylic acids and sodium azide.[10]
  • Immunosuppressant agent cyclosporin by solid-phase peptide synthesis.[11]
  • Allyl azides from allyl alcohols and sodium azide in one pot method.[12]
  • Esterification coupling reagent di-2-thienyl carbonate, from 2(5H)-thiophenone.[13]
  • 2-Chloronicotinaldehydes via cyclization of the corresponding enamides.[14]

Pittogrammi

Skull and crossbonesCorrosion

Avvertenze

Danger

Indicazioni di pericolo

Classi di pericolo

Acute Tox. 1 Inhalation - Skin Corr. 1B

Codice della classe di stoccaggio

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

Classe di pericolosità dell'acqua (WGK)

WGK 2

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges


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Aldrichimica Acta, 21, 47-47 (1988)
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)
A simple one-pot method for the preparation of allyl azides from allyl alcohols using triphosgene: Synthesis of N1-cinnamyl azetidin-2-ones
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Convenient route to thiocarbonates from alcohols, thiols, and triphosgene
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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)

Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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