1,1'-Thiocarbonyldiimidazole
Synonym(s):TCDI
- CAS NO.:6160-65-2
- Empirical Formula: C7H6N4S
- Molecular Weight: 178.21
- MDL number: MFCD00005289
- EINECS: 228-183-4
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-04 13:44:46
What is 1,1'-Thiocarbonyldiimidazole?
Chemical properties
yellow powder
The Uses of 1,1'-Thiocarbonyldiimidazole
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.
The Uses of 1,1'-Thiocarbonyldiimidazole
1,1’Thiocarbonyldiimidazole can be used to deoxygenate carboxylic monosaccharide analogues.
What are the applications of 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 -
Properties of 1,1'-Thiocarbonyldiimidazole
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 |
Water Solubility | decomposes |
Sensitive | Moisture Sensitive |
BRN | 609349 |
Stability: | Stable, but air and moisture sensitive. Incompatible with strong oxidizing agents, strong acids. |
CAS DataBase Reference | 6160-65-2(CAS DataBase Reference) |
Safety information for 1,1'-Thiocarbonyldiimidazole
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P280:Wear protective gloves/protective clothing/eye protection/face protection. P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P405:Store locked up. |
Computed Descriptors for 1,1'-Thiocarbonyldiimidazole
InChIKey | RAFNCPHFRHZCPS-UHFFFAOYSA-N |
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