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330752

Triphosgene

reagent grade, 98%

Synonym(s):

Bis(trichloromethyl) carbonate

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5 g

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$80.20
$68.17
25 g

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$168.00
$142.80
100 g

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$569.00
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500 g

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About This Item

Linear Formula:
Cl3COCOOCCl3
CAS Number:
Molecular Weight:
296.75
UNSPSC Code:
12352108
NACRES:
NA.22
PubChem Substance ID:
EC Number:
250-986-3
Beilstein/REAXYS Number:
1787583
MDL number:
Assay:
98%
Form:
powder

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grade

reagent grade

Quality Segment

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

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.

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This Item
367907P52652539899
description

reagent grade, 98%

description

98%

description

ReagentPlus®, 99%

description

97%

assay

98%

assay

98%

assay

99%

assay

97%

Quality Level

200

Quality Level

100

Quality Level

200

Quality Level

200

reaction suitability

reaction type: Coupling Reactions

reaction suitability

-

reaction suitability

-

reaction suitability

reaction type: Carbonylations

storage temp.

2-8°C

storage temp.

-

storage temp.

-

storage temp.

-

bp

203-206 °C (lit.)

bp

-

bp

240 °C (lit.)

bp

-

form

powder

form

solid

form

liquid

form

-


pictograms

Skull and crossbonesCorrosion

signalword

Danger

hcodes

Hazard Classifications

Acute Tox. 1 Inhalation - Skin Corr. 1B

Storage Class

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

ppe

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



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Questions

1–2 of 2 Questions  
  1. 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/418/501/product-dating-information-06-25-mk.pdf

      Helpful?

  2. 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

      Helpful?

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