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HomeProduct name list1,1'-Thiocarbonyldiimidazole

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
1,1'-Thiocarbonyldiimidazole Structural

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)
ghs
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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