1,1'-Thiocarbonyldiimidazole

1,1'-Thiocarbonyldiimidazole Basic information

Product Name:	1,1'-Thiocarbonyldiimidazole
Synonyms:	N,N'-THIOCARBONYLDIIMIDAZOLE;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)
CAS:	6160-65-2
MF:	C7H6N4S
MW:	178.21
EINECS:	228-183-4
Product Categories:	Carbonyldiimidazole Derivatives;Coupling;Synthetic Reagents;Carbonyldiimidazole DerivativesBuilding Blocks;Heterocyclic Building Blocks;Imidazoles
Mol File:	6160-65-2.mol

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 Information

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

1,1'-Thiocarbonyldiimidazole Usage And Synthesis

Chemical Properties	yellow powder
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.
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.
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

Preparation Products

1-Methyl-2-imidazolidinethione-->3-PHENYLPROPYL ISOTHIOCYANATE-->(S)-4-PHENYL-1,3-OXAZOLIDINE-2-THIONE-->bis(benzylsulfanyl)methanethione-->4-Isothiocyanatobenzene-1-sulfonamide-->4,4-DIMETHYL-2-OXAZOLIDINONE-->Di-o-tolythiourea-->3-CHLOROPHENYL ISOTHIOCYANATE-->4-(TRIFLUOROMETHYL)PHENYL ISOTHIOCYANATE-->NAPHTHALENE, 1-CYCLOPROPYL-4-ISOTHIOCYANATO--->3-CHLORO-4-FLUOROPHENYL ISOTHIOCYANATE-->1,2,4-Triazolo[4,3-b]pyridazine-6-carboxylic acid, 2,3-dihydro-3-thioxo-, methyl ester-->N-(1H-INDAZOL-6-YL)THIOUREA-->1H-Imidazole-1-carbothioic acid, O-propyl ester-->Benzene, 1-fluoro-4-(2-isothiocyanatoethyl)--->Dimorpholino thioketone

1,1'-Thiocarbonyldiimidazole

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