6160-65-2

1,1'-Thiocarbonyldiimidazole (TCDI,6160-65-2) is an imidazole compound that can be prepared by reacting thiophosphoryl chloride with two corresponding imidazoles.  Its structure has two imidazole rings, and the imidazole groups can be rapidly displaced, making it a safer alternative to thiophosphoryl chloride.  TCDI is used as an organic synthesis or chemical reaction reagent for the synthesis of thiosemicarbazones and thioamides.  It is also used in the Corey-Winter olefin synthesis and in the Barton-McCombie deoxygenation reaction.  In addition, it is the sulfur analogue of the peptide addition reagent carbodiimidazole (CDI), which is used to couple peptides.

yellow powder

1,1′-Thiocarbonyldiimidazole (TCDI,6160-65-2) is generally used as a reagent to carry out the deoxygenation of vicinal diols by forming cyclic thionocarbonate in Corey-Winter alkene synthesis.
It is used as a reagent in the enantioselective total synthesis of (+)-hapalindole Q, 12-epi-fischerindole U and welwitindolinone A.
It is also used in the preparation of trithiocarbonates, xanthates, and dithiocarbamates as chain transfer agents for the reversible addition fragmentation chain transfer and macromolecular design (RAFT/ MADIX) polymerization.

1,1’Thiocarbonyldiimidazole(6160-65-2) can be used to deoxygenate carboxylic monosaccharide analogues.

The Journal of Organic Chemistry, 43, p. 337, 1978 DOI: 10.1021/jo00396a035

It forms yellow crystals on recrystallisation from tetrahydrofuran or by sublimation at 10-3torr (bath temperature 70-80o). It is hydrolysed by H2O and should be stored dry. [Staab & Walther Justus Liebigs Ann Chem 657 98 1962; Pullukat et al. Tetrahedron Lett 1953 1967, Hanessian et al. Can J Chem 65 1859 1987, Rajanbabu et al. J Am Chem Soc 111 1759 1989.] Thiochrome {2,7-dimethyl-5H -thiachromine-8-ethanol; 3,8-dimethyl-2-hydroxyethyl-5H -