1,1'-Thiocarbonylbis(imidazol)
1,1'-Thiocarbonyldiimidazole
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Grundinformationen
- CAS
6160-65-2- Standard-SMILES
S=C(n1ccnc1)n1ccnc1- InChIKey
RAFNCPHFRHZCPS-UHFFFAOYSA-N- Summenformel
- C7H6N4S
- Durchschnittliche Molmasse
- 178,22 g/mol
- Monoisotopische Masse
- 178,03131719
Namen und Bezeichner
- Bevorzugter Name
- 1,1'-Thiocarbonyldiimidazole
- IUPAC
- di(imidazol-1-yl)methanethione
- Lokaler Name
- 1,1'-Thiocarbonylbis(imidazol)
- Englischer Name
- 1,1'-Thiocarbonyldiimidazole
- Summenformel
- C7H6N4S
- Molmasse
- 178.21
Namen und Synonyme
1,1'-ThiocarbonyldiimidazoleRefChem:8977676160-65-2ThiocarbonyldiimidazoleN,N'-Thiocarbonyldiimidazoledi(imidazol-1-yl)methanethionedi(1H-imidazol-1-yl)methanethione1,1-ThiocarbonyldiimidazoleMFCD000052891H-Imidazole, 1,1'-carbonothioylbis-N,N-ThiocarbonyldiimidazoleTCDI
Weitere Namen anzeigen
Thiocarbonyl diimidazolebis(1H-imidazol-2-yl)methanethioneDiiMidazdiimidazoL1,1'-THIOCARBONYL1,1'-Thiocarbonyldii
Thiocarbonylbisimidazole1,1'-Thiocarbonylbis(imidazole)Di-1H-imidazol-1-ylmethanethione1,1'-Carbonothioylbis-1H-imidazoleH8A75XB5AY1,1'-(Thiocarbonyl)diimidazole1-(1H-imidazole-1-carbothioyl)-1H-imidazoledi-1H-imidazol-1-ylmethanethion
Datenbank-Bezeichner
- CAS
6160-65-2- PubChem CID
- 80264
- DTXSID
DTXSID70210614- UNII
- H8A75XB5AY
- EC Number
- 228-183-4
- Nikkaji
- J5.204C
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 0,7
- Polarare Oberfläche (TPSA)
- 67,7 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 12
- Formalladung
- 0
- Komplexität
- 166
Experimentelle und physikochemische Eigenschaften
Chemical ClassesNitrogen Compounds -> Imidazoles
Physical DescriptionYellow powder; [Alfa Aesar MSDS]
Physikochemische Eigenschaften
- Schmelzpunkt
- 98 · 98-102 °C(lit.)
- Siedepunkt
- 342 °C · 342°C (rough estimate)
- Dichte
- 1.3046 · 1.3046 (rough estimate)
- Brechungsindex
- 1.55 · 1.5500 (estimate)
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- Soluble in terahydrofuran, toluene and dichloromethane.
- pka
- 1.96 · 1.96±0.10(Predicted)
- Aggregatzustand
- Powder
- Farbe
- Bright yellow
- Wasserlöslichkeit
- decomposes
- BRN
- 609349 · 609349
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 6.7% (1 of 15) of reports.
Warning
H302 (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.
Gefahrenhinweise
Regulatory Information
Chemical: 1H-Imidazole, 1,1'-carbonothioylbis-
Status: No longer Valid Update: 03-12-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/32005
1H-Imidazole, 1,1'-carbonothioylbis-: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationEvaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia
Hazards SummaryAn irritant; Harmful by ingestion; [Alfa Aesar MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (53.3%)
Sicherheitsdaten
- F
- 9-21
- wgk
- 3
- hs_code
- 29332900
- risk_code
- 22-34
- hazard_code
- Xi
Chemie und Industrie
Anwendungen
Beschreibung1,1'-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.
Verwenden1,1'-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.
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