1, 1'-Thiocarbonyldiimidazole: An organic compound that acts as a coupling or condensing agent for the synthesis of polyamides, modified polyolefin, and polypeptide
1, 1'-Thiocarbonyldiimidazole (TCDI) is an organic compound found in a white crystalline solid form. The compound is thiourea containing two imidazole rings and is the sulfur analog of the peptide coupling reagent carbonyldiimidazole. It is basically used for coupling of amino acids for peptide synthesis and also used as an essential reagent in biochemical synthesis. The reagent is used for deoxygenation of alcohols with tributyltin hydride and diols with lithium aluminum hydride. 1, 1'-Thiocarbonyldiimidazole (TCDI) is commercially available in the market but it can also be formulated via the reaction of thiophosgene with two equivalents of imidazole. On 1, 1'-Thiocarbonyldiimidazole, the imidazole group can be easily displaced making the compound act as a safer alternative to thiophosgene. This behavior of the compound is generally utilized in the Corey-Winter olefin synthesis. 1, 1'-Thiocarbonyldiimidazole also replace carbonothioyl species (RC(S) Cl) in the Barton–McCombie deoxygenation.
Applications of 1, 1'-Thiocarbonyldiimidazole are as follows: -
• Generally, 1, 1'-Thiocarbonyldiimidazole is used as a reagent to carry out the deoxygenation of vicinal diols by producing cyclic thionocarbonate in Corey-Winter alkene synthesis. • The compound is used as a reagent in the enantioselective total synthesis of (+)-hapalindole Q, welwitindolinone A, and 12-epi-fischerindole U. • The compound is also utilized in the formulation of xanthates, trithiocarbonates, and dithiocarbamates which are the chain transfer agents for the reversible addition fragmentation chain transfer and macromolecular design (RAFT/ MADIX) polymerization.
Properties of 1, 1'-Thiocarbonyldiimidazole are: -
• The melting point of 1, 1'-Thiocarbonyldiimidazole is 98-102 degree Celsius. • The boiling point of 1, 1'-Thiocarbonyldiimidazole is 342 degree Celsius (Approximately). • The density of 1, 1'-Thiocarbonyldiimidazole is 1.3046 (Approximately). • The Refractive index of 1, 1'-Thiocarbonyldiimidazole is 1.5500. • The Storage temperature of 1, 1'-Thiocarbonyldiimidazole is 2-8 degree Celsius. • The compound is soluble in tetrahydrofuran, toluene, and dichloromethane. • The compound is available in powder form and is yellow in color. • The compound is stable but it is moisture and air sensitive. • It is incompatible with strong oxidizing agents and strong acids.
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