1,1'-Thiocarbonylbis(imidazol)

Bezeichnung:1,1'-Thiocarbonylbis(imidazol)

CAS-Nr6160-65-2

Englisch Name:1,1'-Thiocarbonyldiimidazole

CBNumberCB0280138

SummenformelC7H6N4S

Molgewicht178.21

MOL-Datei6160-65-2.mol

Synonyma

1,1'-Thiocarbonylbis(imidazol)

1,1'-Thiocarbonylbis(imidazol) physikalisch-chemischer Eigenschaften

Schmelzpunkt	98-102 °C(lit.)
Siedepunkt	342°C (rough estimate)
Dichte	1.3046 (rough estimate)
Brechungsindex	1.5500 (estimate)
storage temp.	2-8°C
Löslichkeit	Soluble in terahydrofuran, toluene and dichloromethane.
pka	1.96±0.10(Predicted)
Aggregatzustand	Powder
Farbe	Bright yellow
Wasserlöslichkeit	decomposes
Sensitive	Moisture Sensitive
BRN	609349
Stabilität	Stable, but air and moisture sensitive. Incompatible with strong oxidizing agents, strong acids.
InChIKey	RAFNCPHFRHZCPS-UHFFFAOYSA-N
CAS Datenbank	6160-65-2(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	22-34
S-Sätze:	22-24/25-45-36/37/39-26
WGK Germany	3
F	9-21
Hazard Note	Irritant/Keep Cold/Moisture Sensitive
HS Code	29332900

Gefahreninformationscode (GHS)

1,1'-Thiocarbonyldiimidazole Chemische Eigenschaften,Einsatz,Produktion Methoden

S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
Beschreibung
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.
Chemische Eigenschaften
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.
Verwenden
1,1’Thiocarbonyldiimidazole can be used to deoxygenate carboxylic monosaccharide analogues.
Verwenden
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
läuterung methode
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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