1,1'-Thiocarbonylbis(imidazol)
TCDI · Di(1H-imidazol-1-yl)methanethione · 1,1-THIOCARBONYLDIIMIDAZOLE · Thiocarbonyl diimidazole · Di(imidazol-1-yl)methanethione · bis(1H-imidazol-2-yl)methanethione · DiiMidaz · diimidazoL
Identifikatoren & physikalische Daten
| CAS No. | 6160-65-2 |
|---|---|
| Summenformel | C7H6N4S |
| Durchschnittliche Molmasse | 178,22 g/mol |
| Monoisotopische Masse | 178,03131719 g/mol |
| SMILES | S=C(n1ccnc1)n1ccnc1 |
| InChIKey | RAFNCPHFRHZCPS-UHFFFAOYSA-N |
| PubChem CID | 80264 |
| EC No. | 228-183-4 |
| DTXSID | DTXSID70210614 |
| Lokaler Name | 1,1'-Thiocarbonylbis(imidazol) |
Chemische & physikalische Eigenschaften
| XLogP | 0,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 67,7 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 12 |
| Formalladung | 0 |
| Komplexität | 166 |
| Stoffklassen | Nitrogen Compounds -> Imidazoles |
| Physical Description | Yellow powder[Alfa Aesar MSDS] |
| Schmelzpunkt | 98-102 °C(lit.) |
| Siedepunkt | 342°C (rough estimate) |
| Dichte | 1.3046 (rough estimate) |
| Brechungsindex | 1.5500 (estimate) |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | Soluble in terahydrofuran, toluene and dichloromethane.decomposes |
| pKa (Säurekonstante) | 1.96±0.10(Predicted) |
| Aggregatzustand | Powder |
| Farbe | Bright yellow |
| BRN | 609349 |
| Stabilität | Stable, but air and moisture sensitive. Incompatible with strong oxidizing agents, strong acids. |
| InChI | 1S/C7H6N4S/c12-7(10-3-1-8-5-10)11-4-2-9-6-11/h1-6H |
| InChIKey | RAFNCPHFRHZCPS-UHFFFAOYSA-N |
| SMILES | S=C(n1ccnc1)n2ccnc2 |
| CAS Datenbank | 6160-65-2(CAS DataBase Reference) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 6.7% (1 of 15) of reports.WarningH302 (53.3%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 15 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: 1H-Imidazole, 1,1'-carbonothioylbis-Status: No longer Valid Update: 03-12-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/320051H-Imidazole, 1,1'-carbonothioylbis-: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | Evaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia |
| Gefahrenübersicht | An irritantHarmful by ingestion[Alfa Aesar MSDS] |
| Hazard Classes and Categories | Acute Tox. 4 (53.3%) |
| F | 9-21 |
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 29332900 |
| R-Sätze (R) | 22-34 |
| Gefahrensymbole | Xi |
| hazard_note | Irritant/Keep Cold/Moisture Sensitive |
| Sicherheitshinweise (S) | 22-24/25-45-36/37/39-26 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2 |
Anwendungen & Verwendung
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.
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.