| Identification | More | [Name]
1,1'-Thiocarbonyldiimidazole | [CAS]
6160-65-2 | [Synonyms]
1,1'-CARBONOTHIOYLBIS-1H-IMIDAZOLE
1,1'-thiocarbonylbis(imidazole)
1,1'-THIOCARBONYLDIIMIDAZOLE
1,1-THIOCARBONYLDIIMIDAZOLE
N,N'-THIOCARBONYLDIIMIDAZOLE
TCDI
Thiocarbonyl diimidazole
1,1'-THIOCARBONYLDIIMIDAZOLE, TECH., 90%
N,N'-THIOCARBONYLDIIMIDAZOLE(TCDI)
1,1,-ThiocarbonyldiimidazoleTech90%
1,1'-Thiocarbonyldiimidazole,95%
1H-Imidazole, 1,1-carbonothioylbis-
N,N’-Thiocarboryldiimidazole
1,1''-THIOCARBONYLDIIMIDAZOLE (TCDI)
Di(imidazol-1-yl)methanethione
Thiocarbonylbisimidazole
Bis(1H-imidazole-1-yl) thioketone
Bis(1-imidazolyl) thioketone | [EINECS(EC#)]
228-183-4 | [Molecular Formula]
C7H6N4S | [MDL Number]
MFCD00005289 | [Molecular Weight]
178.21 | [MOL File]
6160-65-2.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow powder | [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. | [form ]
Powder | [pka]
1.96±0.10(Predicted) | [color ]
Bright yellow | [Stability:]
Stable, but air and moisture sensitive. Incompatible with strong oxidizing agents, strong acids. | [Water Solubility ]
decomposes | [Sensitive ]
Moisture Sensitive | [BRN ]
609349 | [InChI]
1S/C7H6N4S/c12-7(10-3-1-8-5-10)11-4-2-9-6-11/h1-6H | [InChIKey]
RAFNCPHFRHZCPS-UHFFFAOYSA-N | [SMILES]
S=C(n1ccnc1)n2ccnc2 | [CAS DataBase Reference]
6160-65-2(CAS DataBase Reference) |
| Questions And Answer | Back Directory | [Synthesis]
1,1'-Thiocarbonyldiimidazole can be prepared from 1-(trimethylsilyl)imidazole and phosgene in a one-step reaction. 
1-(trimethylsilyl)imidazole (7.7 g, 55 mmol) and 50 mL of dry benzene (distilled from CaH2) were placed in a flame-drying flask equipped with a high-efficiency condenser. The flask was purged with nitrogen and cooled to 0 °C. Phosgene (3.2 g, 28 mmol) was slowly added to the flask using a syringe. After addition, the mixture was stirred at 0 °C for 1 hour. The solvent was removed under vacuum to give a yellow solid. The solid was dried under high vacuum for several days to obtain a yellow solid (4.81 g), with a yield of 98% and a mp of 98-100 degrees. |
| Hazard Information | Back Directory | [Description]
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.
| [Chemical Properties]
yellow powder | [Application]
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.
| [Uses]
1,1’Thiocarbonyldiimidazole(6160-65-2) can be used to deoxygenate carboxylic monosaccharide analogues.
| [Synthesis Reference(s)]
The Journal of Organic Chemistry, 43, p. 337, 1978 DOI: 10.1021/jo00396a035 | [reaction suitability]
reaction type: Carbonylations | [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 - |
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Alfa Aesar
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Energy Chemical
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