1,1'-Thiocarbonyldiimidazole
- Product Name
- 1,1'-Thiocarbonyldiimidazole
- 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
- Formula Weight
- 178.21
- MOL File
- 6160-65-2.mol
1,1'-Thiocarbonyldiimidazole Property
- 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
- 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
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405Store locked up.
N-Bromosuccinimide Price
- Product number
- 156051
- Product name
- 1,1′-Thiocarbonyldiimidazole
- Purity
- technical grade, 90%
- Packaging
- 5g
- Price
- $42.07
- Updated
- 2025/07/31
- Product number
- 156051
- Product name
- 1,1′-Thiocarbonyldiimidazole
- Purity
- technical grade, 90%
- Packaging
- 10g
- Price
- $79.1
- Updated
- 2025/07/31
- Product number
- C1376
- Product name
- 1,1'-Thiocarbonyldiimidazole
- Purity
- >95.0%(GC)(T)
- Packaging
- 5g
- Price
- $146
- Updated
- 2025/07/31
- Product number
- C1376
- Product name
- 1,1'-Thiocarbonyldiimidazole
- Purity
- >95.0%(GC)(T)
- Packaging
- 25g
- Price
- $508
- Updated
- 2025/07/31
- Product number
- 88545
- Product name
- 1,1′-Thiocarbonyldiimidazole
- Purity
- ≥95.0% (S)
- Packaging
- 1g
- Price
- $45.5
- Updated
- 2025/07/31
1,1'-Thiocarbonyldiimidazole Chemical Properties,Usage,Production
Description
1,1'-Thiocarbonyldiimidazole (TCDI) 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
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
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 -
1,1'-Thiocarbonyldiimidazole Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 1,1'-Thiocarbonyldiimidazole manufacturers
- Product
- Thiocarbonyldiimidazole 6160-65-2
- Price
- US $2.00/kg
- Min. Order
- 10kg
- Purity
- 99%
- Supply Ability
- 10000kg
- Release date
- 2025-06-09
- Product
- 1,1'-Thiocarbonyldiimidazole 6160-65-2
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 500000kg
- Release date
- 2024-11-04
- Product
- 1,1'-Thiocarbonyldiimidazole 6160-65-2
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 98%
- Supply Ability
- 1ton
- Release date
- 2022-10-10