Thiocarbonyldiimidazole

Last updated
Thiocarbonyldiimidazole
Thiocarbonyldiimidazole.svg
Names
Preferred IUPAC name
Di(1H-imidazol-1-yl)methanethione
Other names
TCDI
Identifiers
3D model (JSmol)
ECHA InfoCard 100.025.622 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 228-183-4
PubChem CID
UNII
  • InChI=1S/C7H6N4S/c12-7(10-3-1-8-5-10)11-4-2-9-6-11/h1-6H
    Key: RAFNCPHFRHZCPS-UHFFFAOYSA-N
  • C1=CN(C=N1)C(=S)N2C=CN=C2
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).

Contents

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 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]

References

  1. 1 2 Adrian, L. Schwan; Jeffrey, H. Byers (15 March 2007). "1,1′-Thiocarbonyldiimidazole". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/9780470842898.rt094.pub2. ISBN   978-0-471-93623-7.
  2. ↑ Corey, E. J.; Winter, Roland A. E. (September 1963). "A New, Stereospecific Olefin Synthesis from 1,2-Diols". Journal of the American Chemical Society. 85 (17): 2677–2678. Bibcode:1963JAChS..85.2677C. doi:10.1021/ja00900a043.
  3. ↑ Esser, Franz; Roos, Otto (June 1978). "N-Terminal Cyclization of Peptides with N,N′-Carbonyldiimidazole orN,N′-Thiocarbonyldiimidazole". Angewandte Chemie International Edition in English. 17 (6): 467–468. doi:10.1002/anie.197804671.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.