ChemicalBook > Product Catalog >Organic Chemistry >Heterocyclic Compounds >1,1'-Thiocarbonyldiimidazole

1,1'-Thiocarbonyldiimidazole

1,1'-Thiocarbonyldiimidazole Structure
CAS No.
6160-65-2
Chemical Name:
1,1'-Thiocarbonyldiimidazole
Synonyms
TCDI;Di(1H-imidazol-1-yl)methanethione;1,1-THIOCARBONYLDIIMIDAZOLE;Thiocarbonyl diimidazole;bis(1H-imidazol-2-yl)methanethione;DiiMidaz;diimidazoL;1,1'-THIOCARBONYL;1,1'-Thiocarbonyldii;Thiocarbonylbisimidazole
CBNumber:
CB0280138
Molecular Formula:
C7H6N4S
Molecular Weight:
178.21
MOL File:
6160-65-2.mol
MSDS File:
SDS
Modify Date:
2024/5/29 17:03:55

1,1'-Thiocarbonyldiimidazole 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

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Hazard Codes  Xi
Risk Statements  22-34
Safety Statements  22-24/25-45-36/37/39-26
WGK Germany  3
9-21
Hazard Note  Irritant/Keep Cold/Moisture Sensitive
HS Code  29332900
NFPA 704
1
2 1

1,1'-Thiocarbonyldiimidazole price More Price(10)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) 88545 1,1′-Thiocarbonyldiimidazole ≥95.0% (S) 6160-65-2 1G ₹2175.83 2022-06-14 Buy
Sigma-Aldrich(India) 88545 1,1′-Thiocarbonyldiimidazole ≥95.0% (S) 6160-65-2 5G ₹6776.45 2022-06-14 Buy
Sigma-Aldrich(India) 88545 1,1′-Thiocarbonyldiimidazole ≥95.0% (S) 6160-65-2 25G ₹18922.1 2022-06-14 Buy
Sigma-Aldrich(India) 156051 1,1′-Thiocarbonyldiimidazole technical grade, 90% 6160-65-2 5G ₹4611.45 2022-06-14 Buy
Sigma-Aldrich(India) 156051 1,1′-Thiocarbonyldiimidazole technical grade, 90% 6160-65-2 10G ₹7913.08 2022-06-14 Buy
Product number Packaging Price Buy
88545 1G ₹2175.83 Buy
88545 5G ₹6776.45 Buy
88545 25G ₹18922.1 Buy
156051 5G ₹4611.45 Buy
156051 10G ₹7913.08 Buy

1,1'-Thiocarbonyldiimidazole Chemical Properties,Uses,Production

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.

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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