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| 1,1'-Thiocarbonyldiimidazole Basic information |
| 1,1'-Thiocarbonyldiimidazole Chemical Properties |
| Melting point | 98-102 °C(lit.) | | Boiling point | 342°C (rough estimate) | | density | 1.3046 (rough estimate) | | refractive index | 1.5500 (estimate) | | storage temp. | 2-8°C | | solubility | Soluble in terahydrofuran, toluene and dichloromethane. | | pka | 1.96±0.10(Predicted) | | form | Powder | | color | Bright yellow | | Water Solubility | decomposes | | Sensitive | Moisture Sensitive | | BRN | 609349 | | Stability: | Stable, but air and moisture sensitive. Incompatible with strong oxidizing agents, strong acids. | | InChIKey | RAFNCPHFRHZCPS-UHFFFAOYSA-N | | CAS DataBase Reference | 6160-65-2(CAS DataBase Reference) |
| 1,1'-Thiocarbonyldiimidazole Usage And Synthesis |
| Chemical Properties | yellow powder | | Uses | 1,1’Thiocarbonyldiimidazole can be used to deoxygenate carboxylic monosaccharide analogues. | | Uses | 1,1'-Thiocarbonyldiimidazole is used as a reagent for the deoxygenation of alcohols with tributyltin hydride and diols with lithium aluminum hydride. It is also used to deoxygenate carboxylic monosaccharide analogues. Further, it is a useful reagent involved in biochemical synthesis. In addition to this, it is used to prepare 1-[bis-(4-methoxy-phenyl)-methyl]-1H-imidazole by reacting with 4,4'-dimethoxy-benzhydrol. | | Application | 1,1′-Thiocarbonyldiimidazole (TCDI) 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. | | Synthesis Reference(s) | The Journal of Organic Chemistry, 43, p. 337, 1978 DOI: 10.1021/jo00396a035 | | Purification Methods | 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 - |
| 1,1'-Thiocarbonyldiimidazole Preparation Products And Raw materials |
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