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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.
Reacts with diols to give cyclic thionocarbonates which are desulfurized by trialkyl phosphites to give alkenes by cis-elimination of CO2 from the intermediate carbene (Corey-Winter olefination): J. Am. Chem. Soc., 85, 2677 (1963); Angew. Chem. Int. Ed., 14, 753 (1975). For a modified procedure involving ring-opening of the thionocarbonate intermediate with an alkyl iodide, followed by Zn reduction of the resulting iodo ester, see: Tetrahedron Lett., 3793 (1973). Alternatively, the thionocarbonate of a 1,2-diol can be selectively reduced to the methylenedioxy group with Triphenyltin hydride, L00163, under free-radical conditions: J. Org. Chem., 62, 4159 (1997).
Can be used to deoxygenate carbocyclic monosaccharide analogues: Tetrahedron., 48, 2349 (1992).
Ivanov, A. V.; Virus, E. D.; Luzyanin, B. P.; Kubatiev, A. A. Capillary electrophoresis coupled with 1,1'-thiocarbonyldiimidazole derivatization for the rapid detection of total homocysteine and cysteine in human plasma. J. Chromatogr. B 2015, 1004, 30-36.
Chaurand, P. Introducing specificity and sensitivity in imaging MS. Bioanalysis 2015, 7 (18), 2279-2281.
Hazard Statements: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P501c
Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant