HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
1,1'-Carbonylbis-1H-imidazol
CDI · CARBONYLDIIMIDAZOLE · 1,1'-CARBONYLDIIMIDAZOLE (CDI) · DI(1H-IMIDAZOL-1-YL)METHANONE · N,N-CARBONYLDIIMIDAZOLE · N,N'-Carbonyldiimidazole · 1,1-CARBONYL DIIMIDAZOLE · Diimidazolyl ketone
Identifikatoren & physikalische Daten
| CAS No. | 530-62-1 |
|---|---|
| Summenformel | C7H6N4O |
| Durchschnittliche Molmasse | 162,15 g/mol |
| Monoisotopische Masse | 162,05416083 g/mol |
| SMILES | O=C(n1ccnc1)n1ccnc1 |
| InChIKey | PFKFTWBEEFSNDU-UHFFFAOYSA-N |
| PubChem CID | 68263 |
| ChEMBL | CHEMBL3903881 |
| EC No. | 208-488-9 |
| DTXSID | DTXSID9038761 |
| Lokaler Name | 1,1'-Carbonylbis-1H-imidazol |
Chemische & physikalische Eigenschaften
| XLogP | -0,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 52,7 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 12 |
| Formalladung | 0 |
| Komplexität | 166 |
| Physical Description | Solid[Merck Index] White crystalline powder[Alfa Aesar MSDS] |
| Schmelzpunkt | 117-122 °C(lit.) |
| Siedepunkt | 288.83°C (rough estimate) |
| Dichte | 1.303 g/mL at 25 °C |
| Dampfdruck | 0.006-0.012Pa at 20-25℃ |
| Brechungsindex | n20/D1.434 |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | Soluble in dimethylformamide.Insoluble in water |
| pKa (Säurekonstante) | 2.90±0.10(Predicted) |
| Aggregatzustand | Crystalline Powder |
| Farbe | White to light cream |
| pH | 7.7 (50g/l, H2O, 20℃) |
| Merck | 14,1819 |
| BRN | 6826 |
| Stabilität | Stable, but moisture-sensitive. Incompatible with acids, strong oxidizing agents, water. |
| InChI | 1S/C7H6N4O/c12-7(10-3-1-8-5-10)11-4-2-9-6-11/h1-6H |
| InChIKey | PFKFTWBEEFSNDU-UHFFFAOYSA-N |
| SMILES | O=C(n1ccnc1)n2ccnc2 |
| CAS Datenbank | 530-62-1(CAS DataBase Reference) |
| EPA chemische Informationen | 1H-Imidazole, 1,1'-carbonylbis- (530-62-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 0.4% (1 of 233) of reports.DangerH302 (84.1%): Harmful if swallowed [Warning Acute toxicity, oral]H314 (83.3%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]H315 (15.9%): Causes skin irritation [Warning Skin corrosion/irritation]H318 (45.9%): Causes serious eye damage [Danger Serious eye damage/eye irritation]H319 (15.9%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H360 (26.2%): May damage fertility or the unborn child [Danger Reproductive toxicity]H360D (16.3%): May damage the unborn child [Danger Reproductive toxicity]P203, P260, P264, P264+P265, P270, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P318, P321, P330, P332+P317, P337+P317, P362+P364, P363, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 233 reports by companies from 28 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 1 of 233 reports by companies.There are 27 notifications provided by 232 of 233 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatorische Informationen | Chemical: 1H-Imidazole, 1,1'-carbonylbis-Status: Active Update: 30-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/103641,1'-Carbonyldiimidazole: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | Hydrolyzed by water evolving carbon dioxide[Merck Index] Causes burnsInhalation may cause corrosive injuries to upper respiratory tract and lungsHarmful by ingestion[Alfa Aesar MSDS] |
| Hazard Classes and Categories | Acute Tox. 4 (84.1%)Skin Corr. 1B (83.3%)Skin Irrit. 2 (15.9%)Eye Dam. 1 (45.9%)Eye Irrit. 2 (15.9%)Repr. 1B (26.2%)Repr. 1B (16.3%) |
| Unerwünschte Wirkungen | Dermatotoxin - Skin burns.Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors. |
| F | 10-21 |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3263 8/PG 2 |
| Zollcode | 29332990 |
| R-Sätze (R) | 22-34-36/37/38-40-36/38 |
| Toxizität | LD50 orally in Rabbit: 1071 mg/kg |
| Gefahrensymbole | C,Xi,Xn |
| hazard_note | Harmful/Corrosive/Moisture Sensitive |
| Sicherheitshinweise (S) | 26-36/37/39-45-37/39-27-36/37 |
| Gefahrenklasse | 8Acute Tox. 4 OralEye Dam. 1Skin Corr. 1B |
| Verpackungsgruppe | III |
| Lagerklasse | 8A - Combustible corrosive hazardous materials |
Anwendungen & Verwendung
Verwenden
CDI, also known as 1,1'-carbonyldiimidazole, is a commonly used peptide coupling reagent in the synthesis of peptides and nucleoside triphosphates. It usually contains approximately 10% imidazole and reacts rapidly with carboxylic acids to produce acyl imidazoles. Later, it readily reacts with amines to create amides. In addition, CDI is useful in converting alcohols and amines into a range of chemical compounds, including carbamates, esters, and ureas.
Herstellung & Synthese
synthetische
1,1'-Carbonyldiimidazole has been prepared by the reaction of imidazole and phosgene in anhydrous benzene and anhydrous tetrahydrofuran. It has also been obtained by the reaction of 1-(trimethylsilyl)imidazole and phosgene in anhydrous benzene, but that method offers no advantages that justify the more extensive preparative effort required.DOI: 10.15227/orgsyn.048.0044