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)

Safety Information

Hazard Codes 

Xi

Risk Statements 

22-34

Safety Statements 

22-24/25-45-36/37/39-26

WGK Germany 

3

F 

9-21

Hazard Note 

Irritant/Keep Cold/Moisture Sensitive

HS Code 

29332900

MSDS

• Language:English Provider:1,1'-Thiocarbonylbis(imidazole)
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

1,1'-Thiocarbonyldiimidazole Usage And Synthesis

Chemical Properties

yellow powder

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.

Uses

1,1’Thiocarbonyldiimidazole can be used to deoxygenate carboxylic monosaccharide analogues.

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(6160-65-2)Related Product Information

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