1,1'-Thiocarbonylbis(imidazol)

1,1'-Thiocarbonyldiimidazole

HCID 80264CAS 6160-65-2

Grundinformationen

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 Struktureigenschaften

XLogP
0,7
Polarare Oberfläche (TPSA)
67,7 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
0
Schwere Atome
12

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.

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

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 · 3 Einträge

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
hazard_note
Irritant/Keep Cold/Moisture Sensitive

Chemie und Industrie

Anwendungen · 2 Einträge

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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