Thiocarbonyldiimidazole
Chemical compound
From Wikipedia, the free encyclopedia
1,1'-Thiocarbonyldiimidazole (TCDI) is a thiourea containing two imidazole rings.[1] It is the sulfur analog of the peptide coupling reagent carbonyldiimidazole (CDI).
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| Names | |
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| Preferred IUPAC name
Di(1H-imidazol-1-yl)methanethione | |
| Other names
TCDI | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.025.622 |
| EC Number |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C7H6N4S | |
| Molar mass | 178.21 g·mol−1 |
| Melting point | 101 to 103 °C (214 to 217 °F; 374 to 376 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis
TCDI is commercially available but can also be prepared via the reaction of thiophosgene with two equivalents of imidazole.[1]
Reactions
The imidazole groups on TCDI can be easily displaced, allowing it to act as a safer alternative to thiophosgene. This behaviour has been used in the Corey–Winter olefin synthesis.[2] It may also replace thioacyl chlorides (RC(S)Cl) in the Barton–McCombie deoxygenation. Other uses include the synthesis of thioamides and thiocarbamates. Like the analogous CDI, it may be used for peptide coupling.[3]