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
330752
Triphosgene
reagent grade, 98%
Synonym(s):
Bis(trichloromethyl) carbonate
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About This Item
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InChI key
UCPYLLCMEDAXFR-UHFFFAOYSA-N
InChI
1S/C3Cl6O3/c4-2(5,6)11-1(10)12-3(7,8)9
SMILES string
ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl
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
Quality Level
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This Item | 324108 | 167215 | 367907 |
|---|---|---|---|
| assay 98% | assay - | assay 98% | assay 98% |
| Quality Level 200 | Quality Level 100 | Quality Level 100 | Quality Level 100 |
| reaction suitability reaction type: Coupling Reactions | reaction suitability - | reaction suitability - | reaction suitability - |
| mp 79-83 °C (lit.) | mp - | mp −40 °C (lit.) | mp 253-255 °C (lit.) |
| bp 203-206 °C (lit.) | bp - | bp 183.7 °C (lit.) | bp - |
| form powder | form liquid | form liquid | form solid |
General description
It is also commonly employed as a coupling agent in the synthesis of carbonyl compounds.[6][6][7]
[5]
Application
- 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]
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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How is shipping temperature determined? And how is it related to the product storage temperature?
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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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