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Names | |
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Preferred IUPAC name
Di(1H-imidazol-1-yl)methanethione | |
Other names
TCDI
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Identifiers | |
3D model (
JSmol)
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|
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).
|
1,1'-Thiocarbonyldiimidazole (TCDI) is a thiourea containing two imidazole rings. [1] It is the sulfur analog of the peptide coupling reagent carbonyldiimidazole (CDI).
TCDI is commercially available but can also be prepared via the reaction of thiophosgene with two equivalents of imidazole. [1]
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 carbonothioyl species (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]
![]() | |
Names | |
---|---|
Preferred IUPAC name
Di(1H-imidazol-1-yl)methanethione | |
Other names
TCDI
| |
Identifiers | |
3D model (
JSmol)
|
|
ECHA InfoCard | 100.025.622 |
EC Number |
|
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
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).
|
1,1'-Thiocarbonyldiimidazole (TCDI) is a thiourea containing two imidazole rings. [1] It is the sulfur analog of the peptide coupling reagent carbonyldiimidazole (CDI).
TCDI is commercially available but can also be prepared via the reaction of thiophosgene with two equivalents of imidazole. [1]
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 carbonothioyl species (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]