ChemicalBook > CAS DataBase List > 1,1'-Thiocarbonyldiimidazole

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
More
Less

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)
More
Less

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
More
Less

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.

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
Product number
156051
Product name
1,1′-Thiocarbonyldiimidazole
Purity
technical grade, 90%
Packaging
5g
Price
$58.3
Updated
2024/03/01
Sigma-Aldrich
Product number
156051
Product name
1,1′-Thiocarbonyldiimidazole
Purity
technical grade, 90%
Packaging
10g
Price
$110
Updated
2024/03/01
TCI Chemical
Product number
C1376
Product name
1,1'-Thiocarbonyldiimidazole
Purity
>95.0%(GC)(T)
Packaging
5g
Price
$146
Updated
2024/03/01
TCI Chemical
Product number
C1376
Product name
1,1'-Thiocarbonyldiimidazole
Purity
>95.0%(GC)(T)
Packaging
25g
Price
$508
Updated
2024/03/01
Alfa Aesar
Product number
B22008
Product name
1,1'-Thiocarbonyldiimidazole, tech 90%
Packaging
10g
Price
$105
Updated
2024/03/01
More
Less

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

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

More
Less

1,1'-Thiocarbonyldiimidazole Suppliers

Americas 1 Belgium 2 Canada 5 China 364 China Hong Kong 1 Europe 4 Germany 6 India 25 Japan 7 Poland 1 Slovakia 1 South Korea 2 Switzerland 2 Ukraine 2 United Kingdom 19 United States 39 Global 481
R&D Scientific Inc.
Tel
+1-2266000236
Email
sales@rdscientific.com
Country
Canada
ProdList
1609
Advantage
58
Toronto Research Chemicals
Tel
--
Fax
--
Email
info@trc-canada.com
Country
Canada
ProdList
6038
Advantage
71
Canada Fine Chemicals & Scientific Inc., (CFC Scientific Inc.)
Tel
--
Fax
--
Email
es@cfcscientific.com
Country
Canada
ProdList
239
Advantage
58
Maya Biotech
Tel
--
Fax
--
Email
mayabiotech@gmail.com
Country
Canada
ProdList
40
Advantage
42
AB Chemicals Inc.
Tel
--
Fax
--
Email
sales@abcheminc.com
Country
Canada
ProdList
1128
Advantage
47
More
Less

View Lastest Price from 1,1'-Thiocarbonyldiimidazole manufacturers

Shaanxi Dideu Medichem Co. Ltd
Product
1,1'-Thiocarbonyldiimidazole 6160-65-2
Price
US $0.00-0.00/KG
Min. Order
5mg
Purity
99%HPLC
Supply Ability
2000tons
Release date
2020-01-06
Hebei Weibang Biotechnology Co., Ltd
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
Hebei Chuanghai Biotechnology Co,.LTD
Product
Thiocarbonyldiimidazole 6160-65-2
Price
US $2.00/kg
Min. Order
10kg
Purity
99%
Supply Ability
10000kg
Release date
2024-08-20

6160-65-2, 1,1'-ThiocarbonyldiimidazoleRelated Search:

1,1'-Carbonyldiimidazole Imidazole Fenbendazole Albendazole N,O-Bis(trimethylsilyl)acetamide N,N'-Dibenzyl ethylenediamine diacetate N,N'-Diisopropylcarbodiimide N,N-Dimethyl-p-toluidine N,N'-Disuccinimidyl carbonate 1,1,2-TRICHLORO-2,3,3-TRIFLUOROCYCLOBUTANE Nickel carbonyl powder Sodium thiosulfate pentahydrate Adapalene Methimazole 1-Methylimidazole 1,1'-Thiocarbonyldiimidazole

  • N,N'-THIOCARBONYLDIIMIDAZOLE
  • TCDI
  • 1,1'-thiocarbonylbis(imidazole)
  • 1,1'-THIOCARBONYLDIIMIDAZOLE
  • 1-(1H-IMidazol-1-ylcarbothioyl)-1H-iMidazole
  • DiiMidaz
  • 1,1'-CARBONOTHIOYLBIS-1H-IMIDAZOLE
  • N, N - sulfur carbonyl iMidazole
  • 1,1'-Thiocarbonyldiimidazole >=95.0% (S)
  • 1,1'-Thiocarbonyldiimidazole technical grade, 90%
  • 1,1'-Thiocarbonyldiimidazole, technical, 90%
  • 1,1'-THIOCARBONYL
  • 1,1-THIOCARBONYLDIIMIDAZOLE
  • Thiocarbonyl diimidazole
  • 1,1'-THIOCARBONYLDIIMIDAZOLE, TECH., 90%
  • N,N'-THIOCARBONYLDIIMIDAZOLE(TCDI)
  • 1,1,-ThiocarbonyldiimidazoleTech90%
  • 1,1'-Thiocarbonyldiimidazole,95%
  • 1H-Imidazole, 1,1-carbonothioylbis-
  • N,N’-Thiocarboryldiimidazole
  • 1,1''-THIOCARBONYLDIIMIDAZOLE (TCDI)
  • Bis(1H-imidazole-1-yl) thioketone
  • Bis(1-imidazolyl) thioketone
  • Di(imidazol-1-yl)methanethione
  • Thiocarbonylbisimidazole
  • 1,1'-Thiocarbonyldiimidazole,90%,tech.
  • 1.1'-Thiocarbonyldiimidazole 100mg [6160-65-2]
  • 1,1'-Thiocarbonyldiimidazole, tech 90%
  • 1,1'-Thiocarbonyldii
  • N'-ThiocarbonyldiiMidazole(TCDI)
  • 1,1'-Thiocarbonyldi(1H-imidazole) 90%
  • Di(1H-imidazol-1-yl)methanethione
  • bis(1H-imidazol-2-yl)methanethione
  • diimidazoL
  • 1,1'-Thiocarbonyldiimidazole &gt
  • Methanethione, di-1H-imidazol-1-yl-
  • 1,1'-Thicarbonyldiimidazole
  • TIANFU-CHEM 6160-65-2 1,1'-Thiocarbonyldiimidazole
  • THEOCARBONYL DIIMIDAZOLE
  • 1,1'-Thiocarbonyldiimidazole
  • N,N'-Thiocarbonyldiimidazole
  • 6160-65-2
  • 228-183-4
  • Building Blocks
  • Carbonyldiimidazole Derivatives
  • Synthetic Reagents
  • Imidazoles
  • Coupling
  • Heterocyclic Building Blocks
  • Carbonyldiimidazole Derivatives
  • Coupling
  • Synthetic Reagents
  • Carbonyldiimidazole DerivativesBuilding Blocks
  • Heterocyclic Building Blocks
  • Imidazoles